(E)-4-(2-cyanovinyl)benzonitrile | 27519-25-1

• 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: (E)-4-(2-cyanovinyl)benzonitrile
• 英文别名: trans-p-cyanocinnamonitrile；4-[(E)-2-cyanovinyl]benzonitrile；4-[(E)-2-cyanoethenyl]benzonitrile
• CAS: 27519-25-1
• 化学式: C₁₀H₆N₂
• 分子量: 154.171
• InChiKey: GUYNBGVJDVSEGA-OWOJBTEDSA-N

物化性质

• 沸点：
  348.9±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(2-cyanovinyl)benzonitrile 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.75h， 生成 ethyl 2-chloro-5-{[3-cyano-4-(4-cyanophenyl)-5-methyl-1H-pyrrol-1-yl]methyl}pyridine-3-carboxylate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 4-phenylpyrrole derivatives as novel androgen receptor antagonists

  摘要：

  A series of 4-phenylpyrrole derivatives D were designed, synthesized, and evaluated for their potential as novel orally available androgen receptor antagonists therapeutically effective against castration-resistant prostate cancers. 4-Phenylpyrrole compound 1 exhibited androgen receptor (AR) antagonistic activity against T877A and W741C mutant-type ARs as well as wild-type AR. An arylmethyl group incorporated into compound 1 contributed to enhancement of antagonistic activity. Compound 4n, 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile exhibited inhibitory effects on tumor cell growth against the bicalutamide-resistant LNCaP-cxD2 cell line as well as the androgen receptor-dependent JDCaP cell line in a mouse xenograft model. These results demonstrate that this series of pyrrole compounds are novel androgen receptor antagonists with efficacy against prostate cancer cells, including castration-resistant prostate cancers such as bicalutamide-resistant prostate cancer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.067
• 作为产物：
  描述：

  对氰基苯甲酸 在 palladium dichloride 异喹啉 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-4-(2-cyanovinyl)benzonitrile
  参考文献：
  名称：

  Pd-Catalyzed Decarbonylative Olefination of Aryl Esters: Towards a Waste-Free Heck Reaction

  摘要：

  DOI：

  10.1002/1521-3773(20020402)41:7<1237::aid-anie1237>3.0.co;2-f

文献信息

• Pd(II)-Catalyzed C═C Bond Cleavage by a Formal Group-Exchange Reaction
  作者：Runyou Ye、Maoshuai Zhu、Xufei Yan、Yang Long、Ying Xia、Xiangge Zhou

  DOI：10.1021/acscatal.1c01850

  日期：2021.7.16

  A chelation-assisted palladium-catalyzed C═C bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1═C2 + C3 → C1═C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity

  α的螯合辅助钯催化的C = C键的断裂，β不饱和酮向腈的存在形式烯腈，公开了一种正式基交换反应的配制为C的基础上，1 = C 2 + C 3 →C 1 = C 3 + C 2，从正常烯烃氧化裂解和复分解型不同。分离出的关键活性 Pd(II) 配合物以及氘标记实验揭示了螯合基团的必要性，并提出了一条合理的催化途径。
• The reduction of α,β-unsaturated nitriles and α-halonitriles with sodium hydrogen telluride
  作者：Gonzalo Blay、Luz Cardona、Begoña García、Luisa Lahoz、JoséR. Pedro

  DOI：10.1016/0040-4020(96)00401-2

  日期：1996.6

  Sodium hydrogen telluride reacts chemoselectively with α,β-unsaturated nitriles and α-halonitriles linked to aromatic and aliphatic substituents to give the corresponding saturated nitriles with good yields.

  碲化氢钠与α，β-不饱和腈和与芳族和脂族取代基连接的α-卤代腈进行化学选择反应，以高收率得到相应的饱和腈。
• 一种反式α,β-不饱和腈类化合物的制备方法
  申请人：西北师范大学

  公开号：CN106588696B

  公开（公告）日：2018-12-25

  本发明涉及一种反式 α , β ‑不饱和腈类化合物的制备方法，该方法是指依次将苯甲醇类化合物、乙腈、促进剂和碱混合均匀，回流反应完全后得反应液；该反应液依次经常规萃取、干燥、浓缩、柱层析分离后即得反式 α , β ‑不饱和腈类化合物。本发明属双组分一锅反应，条件较温和，原料制备简单易得，操作简单，收率较高，绿色环保经济，可实现规模化生产，在精细化学品方面有着很好的应用潜力，具有较好的工业应用前景。
• [EN] PROCESS FOR HYDROCYANATION OF TERMINAL ALKYNES<br/>[FR] PROCÉDÉ D'HYDROCYANATION D'ALCYNES TERMINAUX
  申请人：STUDIENGESELLSCHAFT KOHLE MBH

  公开号：WO2018210631A1

  公开（公告）日：2018-11-22

  The present invention refers to a process for a Rh-catalyzed Anti-Markovnikov hydrocyanation of terminal alkynes which process discloses, for the first time, the highly stereo- and regio-selective hydrocyanation of terminal alkynes to furnish E- configured alkenyl nitriles and the catalyst used in the present process.

  本发明涉及一种Rh催化的末端炔烃反Markovnikov加氢过程，该过程首次披露了末端炔烃的高立体和区域选择性加氢，以生成E-构型的烯基腈和本过程中使用的催化剂。
• Rh-Catalyzed Anti-Markovnikov Hydrocyanation of Terminal Alkynes
  作者：Fei Ye、Junting Chen、Tobias Ritter

  DOI：10.1021/jacs.7b03749

  日期：2017.5.31

  We report the first highly stereo- and regioselective hydrocyanation of terminal alkynes to furnish E-configured alkenyl nitriles. Acrylonitriles can be accessed on gram scale with broad substrate scope and functional group tolerance. The hydrocyanation reaction employs acetone cyanohydrin as a practical alternative to HCN gas.

  我们报告了第一个高度立体和区域选择性的末端炔烃氢氰化反应，以提供 E 构型的烯基腈。丙烯腈可以在克级获得，具有广泛的底物范围和官能团耐受性。氢氰化反应使用丙酮氰醇作为 HCN 气体的实用替代品。