ethyl (E)-3-chloro-2-cyano-3-phenylpropenoate | 62979-68-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-3-chloro-2-cyano-3-phenylpropenoate
• 英文别名: methyl (E)-3-chloro-2-cyanocinnamate；β-Chlor-α-cyan-zimtsaeure-aethylester；ethyl (E)-3-chloro-2-cyano-3-phenylprop-2-enoate
• CAS: 62979-68-4
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: HJZQRZCRZCQMDQ-ZHACJKMWSA-N

物化性质

• 沸点：
  340.3±42.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氨基吡唑 、 ethyl (E)-3-chloro-2-cyano-3-phenylpropenoate 生成
  参考文献：
  名称：

  Regiochemistry of addition of aminoheterocycles to α-cyanocinnamonitriles: formation of aza-bridged bi- and tricycles

  摘要：

  The additions of various five-membered ring ammoheterocycles to alpha-cyanocinnamonitriles were studied. Regiochemistry of product formation can in most cases be controlled by choosing the appropriate electrophile. An mu-cyanocinnamonitrile with an additional P-leaving group normally provides products arising from initial attack of the ring amino group, while exo attack predominates in the case of the parent alpha-cyanocinnamonitrile. Aminopyrazole and aminoindazole provide only exo products with either electrophile. Product assignments were made via X-ray and 2D NMR methods; these assignments serve as a benchmark to several literature references and to future investigations of conjugate additions of these nucleophiles. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.039
• 作为产物：
  描述：

  ethyl (E) 2-cyano-3-hydroxy-3-phenylpropenoate 生成 ethyl (E)-3-chloro-2-cyano-3-phenylpropenoate
  参考文献：
  名称：

  Jalander Lars F., Synth. Commun, 23 (1993) N 16, S 2293- 2302

  摘要：

  DOI：

文献信息

• Vinylic Nonionic Substitutions of Ethyl (<i>E</i>)- and (<i>Z</i>)-3-Chloro-2-cyano-3-phenylpropenoate by Alcohols
  作者：Lars F. Jalander

  DOI：10.1080/00397919308013787

  日期：1993.8

  title compounds were prepared and the stereochemistry of the nonionic vinylic substitutions by methanol, ethanol, propanol, 2-propanol, and allylalcohol with ethyl (E)- and (Z)-3-chloro-2-cyano-3-phenylpropenoate (2 E,2 Z) in the presence of potassium carbonate, triethylamine and N-methyl-2-pyrrolidone were studied. The reactions with the alcohols gave ethyl (E)-3-alkoxy-2-cyano-3-phe- nylpropenoate

  摘要 制备了标题化合物，并通过甲醇、乙醇、丙醇、2-丙醇和烯丙醇与 (E)- 和 (Z)-3-氯-2-氰基-3-苯基丙烯酸乙酯进行了非离子乙烯基取代的立体化学（ 2 E,2 Z) 在碳酸钾、三乙胺和 N-甲基-2-吡咯烷酮存在下进行了研究。与醇的反应得到 (E)-3-烷氧基-2-氰基-3-苯基丙烯酸乙酯，与起始氯丙烯酸酯（2 E 和 2 Z）的构型无关。反应产物的构型由 NOESY 2D NMR 谱确定。