Tag: M.W=150-200

Wang, Yanping published the artcileAn efficient cyanosilylation of aldehydes with trimethylsilyl cyanide catalysed by MgI₂ etherate, COA of Formula: C8H6ClNO, the publication is Journal of Chemical Research (2012), 36(10), 566-567, database is CAplus.

A convenient procedure for the synthesis of cyanohydrins by the addition of Me₃SiCN to aromatic aldehydes, heteroaromatic aldehydes, aliphatic aldehydes and unsaturated aldehydes catalyzed by MgI₂.(OEt₂)_n in good to excellent yields was described.

Journal of Chemical Research published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, COA of Formula: C8H6ClNO.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Xu, Lili published the artcileProcess improvement on synthesis of 1,4-bis(o-cyanostyryl) benzene, Name: 2-(Chloromethyl)benzonitrile, the publication is Yingyong Huagong (2010), 39(3), 456-458, 462, database is CAplus.

1,4-Dimethylbenzene was chlorinated by dry Cl₂, then the mixed chloride products was hydrolyzed to terephthalaldehyde by hexamethylenetetramine. The purity of the product was 99.5% and the yield was 78.4%. Di-Et o-cyanobenzyl phosphonate was synthesized by the esterification reaction of tri-Et phosphatidate and o-cyanobenzyl chloride dissolved in dimethylbenzene, the yield was 86.5%. 1,4-Bis(o-cyanostyryl) -benzene was synthesized from di-Et o-cyanobenzyl phosphonate and terephthalaldehyde. The purity of the product is 99.5% (HPLC) and the yield is 84.1%.

Yingyong Huagong published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C22H38O2, Name: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Gutierrez-Bonet, Alvaro published the artcileFe-Catalyzed Regiodivergent [1,2]-Shift of α-Aryl Aldehydes, Category: nitriles-buliding-blocks, the publication is Journal of the American Chemical Society (2013), 135(34), 12576-12579, database is CAplus and MEDLINE.

An Fe-catalyzed conversion of aldehydes to ketones via [1,2]-shift has been developed. This skeletal rearrangement shows a wide substrate scope and chemoselectivity profile while exhibiting an excellent [1,2]-aryl or [1,2]-alkyl shift selectivity that is easily switched by electronic effects.

Journal of the American Chemical Society published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Visser, Michael S. published the artcileSynthesis and biological evaluation of novel hygromycin A antibacterial agents, Name: 2-(Chloromethyl)benzonitrile, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(22), 6730-6734, database is CAplus and MEDLINE.

Novel hygromycin A derivatives, e.g. I, bearing a variety of functionalized aminocyclitol moieties have been synthesized in an effort to increase the antibacterial activity and drug-like properties of this class of agents. A systematic study of the effect of alkylation and removal of the hydroxyls of the aminocyclitol directed us to a series of alkylated aminocyclitol derivatives with improved Gram-pos. activity.

Bioorganic & Medicinal Chemistry Letters published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C5H6BNO2, Name: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Yamamoto, Yasunori published the artcileIridium-catalyzed hydroboration of alkenes with pinacolborane, Synthetic Route of 238088-16-9, the publication is Tetrahedron (2004), 60(47), 10695-10700, database is CAplus.

Hydroboration of terminal and internal alkenes with pinacolborane was carried out at room temperature in the presence of an iridium(I) catalyst. Addition of dppm to [Ir(cod)Cl]₂ gave the best catalyst for hydroboration of aliphatic terminal and internal alkenes at room temperature, resulting in addition of the boron atom to the terminal carbon of 1-alkenes with excellent selectivities. On the other hand, a complex prepared from dppe and [Ir(cod)Cl]₂ resulted in the best yields for vinylarenes such as styrene. These complexes exhibited higher levels of catalyst activity and selectivity than those of corresponding rhodium complexes.

Tetrahedron published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C44H28ClFeN4, Synthetic Route of 238088-16-9.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Zhang, Huifang M. published the artcileAntiviral Activity of an Isatin Derivative via Induction of PERK-Nrf2-Mediated Suppression of Cap-Independent Translation, Synthetic Route of 612-13-5, the publication is ACS Chemical Biology (2014), 9(4), 1015-1024, database is CAplus and MEDLINE.

The authors report an isatin derivative 45 (ID45) against coxsackievirus B3 (CVB3) replication, which was synthesized based on a high-throughput screen of a unique natural product library. ID45 showed the most potent anti-CVB3 activity among the four synthesized compounds Treatment of cells with ID45 before or after infection significantly reduced viral particle formation, resulting in protection of cells from virus-induced apoptosis. In addition, ID45 treatment caused remarkable up-regulation of glucose-regulated protein 78 (GRP78), a hallmark of endoplasmic reticulum (ER) stress and an indicator of enhanced cell viability. In identifying the ER stress response pathway induced by ID45, the authors found that ID45 activated PKR-like ER protein kinase (PERK) but failed to up-regulate eIF2α phosphorylation. Instead ID45 activated transcription factor Nrf2 (NF-E2-related factor-2), which is evidenced by its nuclear translocation and upregulation of its downstream target genes NQO1 (NAD(P)H quinone-oxidoreductase 1) and GCLM (glutamate-cysteine ligase, modifier subunit). This observation was further verified by using siRNAs of GRP78 or Nrf2, which blocked both the translocation of Nrf2 and up-regulation of its target genes, leading to aggressive viral replication and enhanced cell apoptosis. Finally, the authors found that ID45-induced up-regulation of NQO1 protected eIF4GI, a eukaryotic cap-dependent translation initiation factor, from cleavage by CVB3 protease and degradation by proteasomes. Taken together, the authors’ findings established that a novel antiviral mechanism of isatin derivative ID45 inhibits CVB3 replication by promoting cell survival through a PERK/Nrf2-dependent ER stress pathway, which benefits host cap-dependent translation but suppresses CVB3 cap-independent translation.

ACS Chemical Biology published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C15H14O3, Synthetic Route of 612-13-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Liu, Da-Chuan published the artcileSynthesis and Anticonvulsant Activity Evaluation of 7-Alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones, Name: 2-(Chloromethyl)benzonitrile, the publication is Archiv der Pharmazie (Weinheim, Germany) (2014), 347(4), 268-275, database is CAplus and MEDLINE.

A new series of 7-alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones were synthesized and evaluated for their anticonvulsant activities. Among these compounds, 7-propoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one and 7-butoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one (I) showed the highest activity against maximal electroshock (MES)-induced tonic extension [(ED)₅₀ = 11.4 and 13.6 mg/kg, resp.]. It is worth mentioning that compound I showed especially low neurotoxicity, which led to a high protective index (PI >51). The orally anticonvulsant activity data of compound I further confirmed its efficacy, in an MES test, and its high safety with a PI value of 50.2. In addition, the potency of compound I against seizures induced by pentylenetetrazole, 3-mercaptopropionic acid, and bicuculline in the chem.-induced seizure tests suggested that compound I may exert its anticonvulsant activity through affecting the GABAergic system.

Archiv der Pharmazie (Weinheim, Germany) published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Name: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wang, Shi-Ben published the artcileSynthesis and evaluation of anticonvulsant and antidepressant activities of 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives, Application In Synthesis of 612-13-5, the publication is Medicinal Chemistry Research (2014), 23(10), 4619-4626, database is CAplus.

7-Alkyl-7H-tetrazolo[1,5-g]purines were synthesized, and their anticonvulsant and antidepressant activities were evaluated in a mouse model. The anticonvulsant effect and neurotoxicity of the compounds were evaluated with a maximal electroshock test and a rotated test in mice, resp. Most of the compounds had anticonvulsant activity. Among the compounds studied, 7-(3-chlorobenzyl)-7H-tetrazolo[1,5-g]purine (I) was the most potent compound with a median ED (ED₅₀) of 28.9 mg/kg and a protective index of 15.8, possessing better anticonvulsant activity and higher safety than carbamazepine. To explain the possible mechanism of anticonvulsant activity, I was tested in pentylenetetrazole-induced seizures, and the results suggest that I exerts anticonvulsant activity through a GABA-mediated mechanism. Forced swimming test showed that at 40 mg/kg, some of the compounds have significant antidepressant activity, the most active compound being 7-(2-chlorobenzyl)-7H-tetrazolo[1,5-g]purine decreasing immobility time by 56%.

Medicinal Chemistry Research published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H7NO4, Application In Synthesis of 612-13-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Becart, Diane published the artcileHelical Oligourea Foldamers as Powerful Hydrogen Bonding Catalysts for Enantioselective C-C Bond-Forming Reactions, Category: nitriles-buliding-blocks, the publication is Journal of the American Chemical Society (2017), 139(36), 12524-12532, database is CAplus and MEDLINE.

Substantial progress has been made toward the development of metal-free catalysts of enantioselective transformations, yet the discovery of organic catalysts effective at low catalyst loadings remains a major challenge. Here we report a novel synergistic catalyst combination system consisting of a peptide-inspired chiral helical (thio)urea oligomer and a simple tertiary amine that is able to promote the Michael reaction between enolizable carbonyl compounds and nitroolefins with excellent enantioselectivities at exceptionally low (1/10,000) chiral catalyst/substrate molar ratios. In addition to high selectivity, which correlates strongly with helix folding, the system we report here is also highly amenable to optimization, as each of its components can be fine-tuned sep. to increase reaction rates and/or selectivities. The predictability of the foldamer secondary structure coupled to the high level of control over the primary sequence results in a system with significant potential for future catalyst design.

Journal of the American Chemical Society published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Cramer, Friedrich published the artcileOcclusion compounds. XVI. Stereospecific reactions with inclusion compounds, HPLC of Formula: 13312-84-0, the publication is Chemische Berichte (1959), 1739-47, database is CAplus.

cf. C.A. 53, 11245h. The following asym. reactions could be carried out with aqueous cyclodextrins (I): (1) asym. conversion of an easily racemizable atropisomeric 4,2-Me(p-MeC₆H₄SO₂)C₆H₃NAcMe (II); (2) synthesis of optically active mandelonitriles; (3) asym. partial oxidation of substituted benzoins; (4) partial saponification of racemic esters to optically active acids. The effect of the I depended on the ratio of the size of the I cavity to the geometric size of the included mol. The analogies to the mode of action of enzymes were discussed. β-I (1.00 g.) in 100 cc. H₂O treated with 0.03 g. II in 60 cc. Et₂O, shaken 7 hrs. at 25°, the Et₂O layer dried briefly, evaporated at 20°, and the residue (0.215 g.) dissolved in CHCl₃ and the rotation measured gave the following values of [α]²⁵_D at the time intervals in hrs. indicated in parentheses: -0.136° (0.33), -0.068° (0.67), -0.007° (15), -0.272° (0) (extrapolated). A similar run with 3.5 hrs. reaction time gave the following values: -0.125° (0.33), -0.063° (0.67), 0.0° (20), -0.250° (0) (extrapolated). α-I (2.0 g.) in 100 cc. pH 9 glycine buffer treated with 2 cc. o-ClC₆H₄CHO then dropwise with 2 g. liquid HCN, stirred 5 hrs. at 22°, extracted with 60 cc. Et₂O, and the Et₂O extract evaporated gave 2.316 g. o-ClC₆H₄CH(OH)CN (III), [α]²⁵_D 0.19° (EtOAc). α-I (1.5 g.) and 2.0 g. powd. p-ClC₆H₄CHO treated in the same manner with 2 g. HCN and stirred 2 hrs. at 22° yielded the p-isomer of III, [α]²⁵_D 0.21° (EtOAc); a portion in 10 cc. concentrated HCl kept 10 min. and worked up gave p-ClC₆H₄CH(OH)CO₂H, [α]²⁵_D -0.37° (EtOAc). 2,2′-Dichlorobenzoin (IV) (2.80 g.) and 1.0 g. α-I in 100 cc. pH 10 glycine buffer shaken 71 hrs. at 25° under O and extracted with 80 cc. Et₂O gave a solution of IV and active (o-ClC₆H₄CO)₂ (V), [α]²⁵_D 0.42; since only 50% active V was present in the oxidation product, the rotation was [α]²⁵_D 0.84°. 4,4′-Dichlorobenzoin (VI) gave similarly during 172 hrs. a solution of 50% VI and 50% (p-ClC₆H₄CO)₂ (VII), [α]²⁵_D 0.32° (EtOAc); pure VII had [α]²⁵_D 0.64°. β-I (1.5 g.) in 100 cc. pH 9 buffer treated with 1 cc. o-ClC₆H₄CH(OH)CO₂Et (VIII), b₁₃ 158-60°, stirred 2.5 hrs. at 58°, basified with 6 cc. 2N NaOH, extracted with EtOAc to isolate the unreacted VIII, the aqueous layer acidified with 25 cc. 4N H₂SO₄, extracted with EtOAc, and the extract evaporated in vacuo at 50° yielded 0.546 g. o-ClC₆H₄CH(OH)CO₂H, [α]²⁵_D 1.19° (EtOAc),and 0.480 g. VlII, [α]²⁵_D -0.73° (EtOAc). PhCHClCO₂Et (IX) (1 cc.), b₁₂ 128-30°, saponified similarly during 3.25 hrs. gave 0.395 g. PhCHClCO₂H, [α]²⁵_D 0.39° (EtOAc), and 0.633 g. IX, [α]²⁵_D -0.20° (EtOH). p-Isomer (X) of VIII (1.35 g.), b₁₆ 167-8°, m. 60-1°, saponified during 2.25 hrs. in pH 9 buffer at 60° yielded 0.417 g. p-ClC₆H⁴CH(OH)CO₂H, [α]²⁵_D 0.38° (EtOAc), and 0.893 g. X, [α]²⁵_D -0.17° (EtOAc). A similar run but at pH 10 and 22° during 6.5 hrs. yielded 0.622 g. acid, [α]²⁵_D 0.16° (EtOAc), and 0.509 g. X, [α]²⁵_D -0.29° (EtOAc). PhCH(OH)CO₂Et(XI) with β-I, and VIII and X with α-I under the same conditions did not yield optically active material. The rates of the ester hydrolyses at constant pH were measured for the following esters (pH, reaction temperature, rates of saponification with 1.32 mmoles β-I and with 1.32 mmoles α-I relative to the rate without I = 1.00, and diameter of ester in A. given): IX, 9.0 ± 0.2, 65°, 1.38, 0.94, 6.7; PhCHBrCO₂Et (b₁₃ 146-8°), 9.0 ± 0.2, 65°, 1.37, 1.01, 6.7; XI, 9.0 ± 0.2, 25°, 1.00, 1.00, 6.2; VIII, 8.0 ± 0.1, 65°, 0.77, 0.94, 8.2; X, 8.0 ± 0.1, 65°, 1.38, 1.05, 6.2.

Chemische Berichte published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, HPLC of Formula: 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts