Month: December 2022

Zheng, Changge published the artcileGeometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF₃ for (E)-Vinyl Trifluoromethyl Thioethers, Application In Synthesis of 5153-73-1, the publication is Organic Letters (2020), 22(12), 4868-4872, database is CAplus and MEDLINE.

An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct C_vinyl-SCF₃ bonds with stable AgSCF₃ as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.

Organic Letters 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 C24H29N5O3, Application In Synthesis of 5153-73-1.

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

Wang, Jian-Shu published the artcileEx Situ Generation of Difluorodiazoethane (CF₂HCHN₂): Application in the Regioselective Synthesis of CF₂H-Containing Pyrazoles, HPLC of Formula: 5153-73-1, the publication is Organic Letters (2019), 21(21), 8751-8755, database is CAplus and MEDLINE.

A new method for the ex situ generation of difluorodiazoethane (CF₂HCHN₂) and a procedure for its efficient use in [3 + 2] cycloaddition with nitroolefins by the AcOH/O₂ catalyst system were developed by using a simple two-chamber system. The method provides a facile and straightforward access to a series of 4-substituted 5-difluoromethyl-3-nitro-1H-pyrazoles that are of interest in medicinal chem. Interestingly, the key factor for the success of this method is the efficient preparation of CF₂HCHN₂ by an ex situ process.

Organic Letters 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 C8H7N3, HPLC of Formula: 5153-73-1.

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

Liu, Tao published the artcileDesign, Synthesis, and Biological Evaluation of Novel 4-Aminopiperidinyl-linked 3,5-Disubstituted-1,2,6-thiadiazine-1,1-dione Derivatives as HIV-1 NNRTIs, Safety of 2-(Chloromethyl)benzonitrile, the publication is Chemical Biology & Drug Design (2015), 86(1), 887-893, database is CAplus and MEDLINE.

A novel series of 4-aminopiperidinyl-linked 3,5-disubstituted-1,2,6-thiadiazine-1,1-dione derivatives I [R = 3-CN, 4-NO₂, 2,4,6-(CH₃)₃, etc.; Ar = 1-naphthyl, 2,4-dichlorophenyl] were designed, synthesized, and evaluated for their in vitro anti-HIV activities in MT-4 cells based on the hybridization of the privileged fragments in DABO and DAPY-typed HIV-1 NNRTIs. Most of the target compounds showed weak inhibitory activity against WT HIV-1. In order to confirm the mode of action of the target compounds, representative compounds I (R = 4-NO₂; Ar = 1-naphthyl) and I (R = 4-NO₂; Ar = 2,4-dichlorophenyl) were selected to perform the HIV-1 RT inhibitory assay. In this assay, I (R = 4-NO₂; Ar = 1-naphthyl) and I (R = 4-NO₂; Ar = 2,4-dichlorophenyl) displayed good activity with IC₅₀ values of 3.15 and 1.52 μM, resp. Addnl., preliminary structure-activity relationships (SARs) anal. and mol. docking studies of newly synthesized compounds were also discussed.

Chemical Biology & Drug Design 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, Safety of 2-(Chloromethyl)benzonitrile.

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

Zou, Shuping published the artcileA integrated process for nitrilase-catalyzed asymmetric hydrolysis and easy biocatalyst recycling by introducing biocompatible biphasic system, COA of Formula: C8H6ClNO, the publication is Bioresource Technology (2021), 320(Part_B), 124392, database is CAplus and MEDLINE.

The whole-cell nitrilase-catalyzed asym. hydrolysis of nitriles is a green and efficient preparation approach for chiral carboxylic acids, but often suffers from toxicity and cell lysis from organic substrates. In this work, a novel integrated process for whole-cell nitrilase-catalyzed asym. hydrolysis was developed for the first time by introducing a biocompatible ionic liquid (IL)-based biphasic system. The whole-cell nitrilases displayed an outstanding stability and recyclability in the biphasic system and still retained > 85% activity even after 7 cycles reaction. A preparative-scale fed-batch hydrolysis of o-chloromandelonitrile to (R)-o-chloromandelic acid (R-CMA) was performed using the integrated process. The results revealed a yield of 91.3% and a space-time yield of 746.4 g·L^-1·d^-1, which are currently the highest reported values for R-CMA biosynthesis. The proposed integrated process avoids substrate inhibition, facilitates the reusability of whole-cell nitrilases, and thus shows great potential for the sustainable production of chiral carboxylic acids.

Bioresource Technology 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 C6H5F4NO3S, COA of Formula: C8H6ClNO.

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

Xu, Han published the artcileSynthesis and herbicidal activities of novel 4-(3-trifluoromethylphenyl)-2H-pyridazin-3-one derivatives, HPLC of Formula: 612-13-5, the publication is Science China: Chemistry (2010), 53(1), 157-166, database is CAplus.

Three series of forty-nine novel 4-(3-trifluoromethylphenyl)-2H-pyridazin-3-one derivatives are designed, synthesized, and evaluated through a Spirodela polyrrhiza test and a greenhouse test. Some compounds show > 80% chlorophyll inhibition of Spirodela polyrrhiza at 10 μg/mL and exhibit some herbicidal activities against Digitaria adscendens in the preemergence treatment at a rate of 150 g/ha. Moreover, the study of the structure-activity relationship (SAR) suggests that the appropriate bulky substituent at the right position is critical for the bleaching and herbicidal activities, which may be useful for the future design of new compounds

Science China: Chemistry 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 C8H10S, HPLC of Formula: 612-13-5.

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

Xiong, Yu-qing published the artcileSynthesis process of diethyl(o-cyanobenzyl)phosphonate, Safety of 2-(Chloromethyl)benzonitrile, the publication is Yingyong Huagong (2014), 43(11), 2012-2013, 2018, database is CAplus.

Aiming at pollution from o-cyanobenzyl chloride and benzene, a green synthesis process was provided by using o-cyanotoluene as starting mol., after photochlorination, o-cyanobenzyl chloride directly reacted with a slight excess of tri-Et phosphate by esterification reaction without adding other organic solvents. The results showed that the optimal technol. condition was chlorination at 140°C, 1.0 of chlorination degree, using incandescent light bulb, esterification at 155°C for 4 h. The critical factor was controlling chlorination degree under 1.0, combination of photochlorination and esterification, in order to reduce pollution to environment.

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 C3H5F3O, Safety of 2-(Chloromethyl)benzonitrile.

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

Lei, Zhen-lin published the artcileSynthesis and antifungal activities of 7-ether coumarin derivatives, Application In Synthesis of 612-13-5, the publication is Huaxue Shiji (2016), 38(2), 157-162, database is CAplus.

7-Hydroxy 4,6-dimethyl-coumarin and 7-hydroxy-4,8-dimethyl-coumarin were synthesized by Peachmann condensation reaction, and then reacted with a substituted benzyl chloride to yield twenty-three new coumarin compounds The structures of all compounds were confirmed by ¹HNMR and LC-MS spectrometry. The preliminary bioassay indicated that compound 7-(4-fluoro-benzyloxy)-4,6-dimethyl-2H-benzopyran-2-one (3c), 4,6-dimethyl-7-(2-methyl-benzyloxy)-2H-pyran-2-one (3j), 7-(4-methoxy-benzyloxy)-4,6-dimethyl-2H-pyran-2-one (3k), 7-(4-fluoro-benzyloxy)-4,8-dimethyl-2H-pyran-2-one (3n) and 7-(4-methoxy-benzyloxy)-4,8-dimethyl-2H-pyran-2-one (3w) showed over 70% antifungal activities against Botryodiplodia theobromae at 100 mg/L, and compound 7-(3-chloro-benzyloxy)-4,8-dimethyl-2H-pyran-2-one (3p) showed broad-spectrum antifungal activity.

Huaxue Shiji 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, Application In Synthesis of 612-13-5.

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

Chen, Chaohuang published the artcilePalladium(II)-Catalyzed Aminotrifluoromethoxylation of Alkenes: Mechanistic Insight into the Effect of N-Protecting Groups, Category: nitriles-buliding-blocks, the publication is Chinese Journal of Chemistry (2020), 38(4), 346-350, database is CAplus.

An efficient palladium-catalyzed regioselective 5-exo aminotrifluoromethoxylation of alkenes was established herein, which provided a practical route toward the synthesis of OCF₃-containing pyrrolidines such as I [R¹ = H, allyl, 4-ClC₆H₄, etc.; R² = allyl, Bn, 4-FC₆H₄, etc.; R¹R² = (CH₂)₃, (CH₂)₄, (CH₂)₂O(CH₂)₂, etc.] and II. Tert-Butyloxycarbonyl (Boc) as an amino protecting group played a significant role in both chemo- and regioselectivities. In addition, preliminary mechanistic studies revealed that amino protecting group of substrates and counter anion of palladium catalyst play critical roles in reaction efficiency presumably due to an isomerization of alkyl- Pd(II) intermediates. Moreover, the asym. 5-exo aminotrifluoromethoxylation reaction had also been achieved by introducing a sterically bulky pyridinyl-oxazoline ligand.

Chinese Journal of Chemistry published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Category: nitriles-buliding-blocks.

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

Ieda, Naoya published the artcilePhotomanipulation of Vasodilation with a Blue-Light-Controllable Nitric Oxide Releaser, Computed Properties of 26187-28-0, the publication is Journal of the American Chemical Society (2014), 136(19), 7085-7091, database is CAplus and MEDLINE.

Spatiotemporally controllable nitric oxide (NO)-releasers allow us to analyze the physiol. effects of NO, a gaseous mediator that modulates many biol. signaling networks, and are also candidate chemotherapeutic agents. We designed and synthesized a blue-light-controllable NO releaser, named NOBL-1, which bears an N-nitrosoaminophenol moiety for NO release tethered to a BODIPY dye moiety for harvesting blue light. Photoinduced electron transfer from N-nitrosoaniline to the antenna moiety upon irradiation with relatively noncytotoxic blue light (470-500 nm) should result in NO release with formation of a stable quinone moiety. NO release from NOBL-1 was confirmed by ESR spin trapping and fluorescence detection. Spatially controlled NO release in cells was observed with DAR-4M AM, a fluorogenic NO probe. We also demonstrated temporally controlled vasodilation of rat aorta ex vivo by blue-light-induced NO release from NOBL-1. This compound should be useful for precise examination of the functions of NO with excellent spatiotemporal control.

Journal of the American Chemical Society published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Computed Properties of 26187-28-0.

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

Schoellkopf, Ulrich published the artcileSyntheses with α-metalated isocyanides. XXIX. Higher amino acids by alkylation of α-metalated ethyl α-isocyanopropionate and alkyl isocyanoacetates, Synthetic Route of 30431-99-3, the publication is Chemische Berichte (1975), 108(5), 1580-92, database is CAplus.

Treatment of α-metalated CNCHR1CO2R2 [R1 = Me, R2 = Et (I); R1 = H, R2 = Et (II); R1 = H, R2 = CMe3 (III)] with alkylating agents (R3X, e.g., R3 = Bu, PhCH2, X = Br, Iodo) gave monoalkylation of I and III but dialkylation of II. Hydrolysis of the alkylated products with HCl/EtOH at 25° or KOH/EtOH at 80° gave R1R3C(NH2)CO2R2 or R1R3C(NHCHO)CO2R2, resp. II and III reacted with 1,2-dibromoethane, bis(2-chloroethyl) ether, and 1,4-dibromobutane to give IV, V, and VI, resp.

Chemische Berichte published new progress about 30431-99-3. 30431-99-3 belongs to nitriles-buliding-blocks, auxiliary class Tetrahydropyran,Nitrile,Ester, name is Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, and the molecular formula is C9H13NO3, Synthetic Route of 30431-99-3.

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