(Z)-3-Chloro-3-(3-chloro-phenyl)-acrylonitrile | 107818-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-Chloro-3-(3-chloro-phenyl)-acrylonitrile
• 英文别名: 3-Chloro-3-(3-chloro-phenyl)-acrylonitrile；3-chloro-3-(3-chlorophenyl)prop-2-enenitrile
• CAS: 107818-32-6
• 化学式: C₉H₅Cl₂N
• 分子量: 198.051
• InChiKey: DGGWSENVWXITNW-UHFFFAOYSA-N

物化性质

• 沸点：
  318.6±30.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-Chloro-3-(3-chloro-phenyl)-acrylonitrile 在 甲醇 、 sodium 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 生成 3-Amino-5-(3-chlorophenyl)-2-thiophenecarboxylic acid
  参考文献：
  名称：

  Novel small molecule inhibitors targeting the “switch region” of bacterial RNAP: Structure-based optimization of a virtual screening hit

  摘要：

  Rising resistance against current antibiotics necessitates the development of antibacterial agents with alternative targets. The "switch region" of RNA polymerase (RNAP), addressed by the myxopyronins, could be such a novel target site. Based on a hit candidate discovered by virtual screening, a small library of 5-phenyl-3-ureidothiophene-2-carboxylic acids was synthesized resulting in compounds with increased RNAP inhibition. Hansch analysis revealed pi (lipophilicity constant) and sigma (Hammet substituent constant) of the substituents at the 5-phenyl moiety to be crucial for activity. The binding mode was proven by the targeted introduction of a moiety mimicking the enecarbamate side chain of myxopyronin into the hit compound, accompanied by enhanced RNAP inhibitory potency. The new compounds displayed good antibacterial activities against Gram positive bacteria and Gram negative Escherichia coli TolC and a reduced resistance frequency compared to the established antibiotic rifampicin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.060
• 作为产物：
  描述：

  3-(3-chlorophenyl)-3-chloropropenal 在 ammonium hydroxide 、 碘 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.75h， 生成 (Z)-3-Chloro-3-(3-chloro-phenyl)-acrylonitrile
  参考文献：
  名称：

  致命的KCN和昂贵的无金属轨道，使用温和的反应条件即可获得β-酮腈

  摘要：

  摘要 已经描述了使用温和的反应条件，使用经济上良性的碘，氨水和氢氧化钠溶液从易于获得的3-氯丙烯一锅合成β-乙腈。该报告提出了一种便捷，廉价，无毒无害，环保的β-乙腈方法。

  DOI：

  10.1080/00397911.2021.1910846

文献信息

• Cyclocarbamate and cyclic amide derivatives
  申请人：——

  公开号：US20020002173A1

  公开（公告）日：2002-01-03

  This invention provides compounds of the formula: 1 wherein A and B are independent substituents selected from S, CH or N; provided that when A is S, B is CH or N; and when B is S, A is CH or N; and A and B cannot both be CH; and when A and B both equal N, one N may be optionally substituted with an C 1 to C 6 alkyl group; R 1 and R 2 are independent substituents selected from the group of H, C 1 to C 6 alkyl, substituted C 1 to C 6 alkyl, C 2 to C 6 alkenyl, substituted C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, substituted C 2 to C 6 alkynyl, C 3 to C 8 cycloalkyl, substituted C 3 to C 8 cycloalkyl, aryl, substituted aryl, heterocyclic, substituted heterocyclic, COR A , or NR B COR A ; or R 1 and R 2 are fused to form optionally substituted 3 to 8 membered spirocyclic alkyl, alkenyl or heterocyclic ring, the heterocyclic ring containing one to three heteroatoms selected from the group of O, S and N; or pharmaceutically useful salts thereof. The compounds of this invention are useful as agonists and antagonists of the progesterone receptor and in methods of inducing contraception and in the treatment or prevention of benign or malignant neoplastic diseases.

  这项发明提供了公式为1的化合物：其中A和B是独立的取代基，选择自S、CH或N；但当A为S时，B为CH或N；当B为S时，A为CH或N；且A和B不能都为CH；当A和B都等于N时，一个N可以选择性地被C1到C6烷基取代；R1和R2是独立的取代基，选择自H、C1到C6烷基、取代的C1到C6烷基、C2到C6烯基、取代的C2到C6烯基、C2到C6炔基、取代的C2到C6炔基、C3到C8环烷基、取代的C3到C8环烷基、芳香族、取代的芳香族、杂环、取代的杂环、CORA或NRBCORA组中的一种；或者R1和R2融合形成选择性取代的3到8成员的螺环烷基、烯基或杂环环，其中杂环环含有1到3个从O、S和N组成的杂原子；或其药学上有用的盐。该发明的化合物可用作孕激素受体的激动剂和拮抗剂，并用于诱导避孕和治疗或预防良性或恶性肿瘤疾病的方法。
• Cyclic regimens using cyclocarbamate and cyclic amide derivatives
  申请人：American Home Products Corporation

  公开号：US06380178B1

  公开（公告）日：2002-04-30

  This invention relates to cyclic combination therapies and regimens utilizing, in combination with progestins, substituted indoline derivative compounds which are antagonists of the progesterone receptor having the general structure: where A and B are independent substituents selected from S, CH or N; provided that when A is S, B is CH or N; and when B is S, A is CH or N; and A and B cannot both be CH; and when A and B both equal N, one N may be optionally substituted with an C1 to C6 alkyl group; R1 and R2 are independent substituents selected from the group of H, C1 to C6 alkyl, substituted C1 to C6 alkyl, C2 to C6 alkenyl, substituted C2 to C6 alkenyl, C2 to C6 alkynyl, substituted C2 to C6 alkynyl, C3 to C8 cycloalkyl, substituted C3 to C8 cycloalkyl, aryl, substituted aryl, heterocyclic, substituted heterocyclic, CORA, or NRBCORA; or R1 and R2 are fused to form optionally substituted 3 to 8 membered spirocyclic alkyl, alkenyl or heterocyclic ring, the heterocyclic ring containing one to three heteroatoms selected from the group of O, S and N; or pharmaceutically useful salts thereof. These methods of treatment may be used for contraception.

  本发明涉及循环联合疗法和方案，其中与孕激素联合使用的取代吲哚啉衍生物化合物作为孕激素受体的拮抗剂，其具有一般结构：其中A和B是独立的取代基，选择自S、CH或N；前提是当A为S时，B为CH或N；当B为S时，A为CH或N；A和B不能同时为CH；当A和B均等于N时，一个N可以选择性地被取代为C1至C6烷基；R1和R2是独立的取代基，选择自H、C1至C6烷基、取代C1至C6烷基、C2至C6烯基、取代C2至C6烯基、C2至C6炔基、取代C2至C6炔基、C3至C8环烷基、取代C3至C8环烷基、芳基、取代芳基、杂环、取代杂环、CORA、或NRCORA；或者R1和R2被融合形成可选择性取代的3至8个成员的螺环烷基、烯基或杂环，其中杂环含有选自O、S和N的一到三个杂原子；或其药用盐。这些治疗方法可用于避孕。
• Novel small molecule inhibitors targeting the “switch region” of bacterial RNAP: Structure-based optimization of a virtual screening hit
  作者：J. Henning Sahner、Matthias Groh、Matthias Negri、Jörg Haupenthal、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2013.04.060

  日期：2013.7

  Rising resistance against current antibiotics necessitates the development of antibacterial agents with alternative targets. The "switch region" of RNA polymerase (RNAP), addressed by the myxopyronins, could be such a novel target site. Based on a hit candidate discovered by virtual screening, a small library of 5-phenyl-3-ureidothiophene-2-carboxylic acids was synthesized resulting in compounds with increased RNAP inhibition. Hansch analysis revealed pi (lipophilicity constant) and sigma (Hammet substituent constant) of the substituents at the 5-phenyl moiety to be crucial for activity. The binding mode was proven by the targeted introduction of a moiety mimicking the enecarbamate side chain of myxopyronin into the hit compound, accompanied by enhanced RNAP inhibitory potency. The new compounds displayed good antibacterial activities against Gram positive bacteria and Gram negative Escherichia coli TolC and a reduced resistance frequency compared to the established antibiotic rifampicin. (C) 2013 Elsevier Masson SAS. All rights reserved.
• The discovery and optimization of pyrimidinone-containing MCH R1 antagonists
  作者：Donald L. Hertzog、Kamal A. Al-Barazanji、Eric C. Bigham、Michael J. Bishop、Christy S. Britt、David L. Carlton、Joel P. Cooper、Alex J. Daniels、Dulce M. Garrido、Aaron S. Goetz、Mary K. Grizzle、Yu C. Guo、Anthony L. Handlon、Diane M. Ignar、Ronda O. Morgan、Andrew J. Peat、Francis X. Tavares、Huiqiang Zhou

  DOI：10.1016/j.bmcl.2006.07.008

  日期：2006.9

  Optimization of a series of constrained melanin-concentrating hormone receptor 1 (MCH RI) antagonists has provided compounds with potent and selective MCH R1 activity. Details of the optimization process are provided and the use of one of the compounds in an animal model of diet-induced obesity is presented. (c) 2006 Elsevier Ltd. All rights reserved.
• Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions
  作者：Pawan K. Sharma、Rajiv Kumar、Sita Ram、Navneet Chandak

  DOI：10.1080/00397911.2021.1910846

  日期：2021.6.18

  synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

  摘要 已经描述了使用温和的反应条件，使用经济上良性的碘，氨水和氢氧化钠溶液从易于获得的3-氯丙烯一锅合成β-乙腈。该报告提出了一种便捷，廉价，无毒无害，环保的β-乙腈方法。