methyl 2-cyano-3-propylacrylate | 288089-53-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-cyano-3-propylacrylate
• 英文别名: Methyl 2-cyano-2-hexenoate；methyl 2-cyanohex-2-enoate
• CAS: 288089-53-2
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: LVYSUCUZCFLAET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  丙二酸二甲酯 、 methyl 2-cyano-3-propylacrylate 在 sodium bromide 作用下， 以 甲醇 为溶剂， 以77%的产率得到trimethyl 2-cyanocyclopropane-3-propyl-1,1,2-tricarboxylate
  参考文献：
  名称：

  Stereoselective electrocatalytic transformation of malonate and alkylidenecyanoacetates into (E)-3-substituted 2-cyanocyclopropane-1,1,2-tricarboxylates

  摘要：

  Electrolysis of malonate and alkylidenecyanoacetates in alcohols in an undivided cell in the presence of NaBr results in stereoselective formation of (E)-3-substituted 2-cyanocyclopropane-1,1,2-tricarboxylates in 75-90% yields. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.02.027

文献信息

• Organocatalytic enantioselective domino synthesis of highly functionalized cyclohexanes with an all-carbon quaternary stereocenter
  作者：Gui-Ling Zhao、Pawel Dziedzic、Farman Ullah、Lars Eriksson、Armando Córdova

  DOI：10.1016/j.tetlet.2009.02.209

  日期：2009.7

  A highly enantioselective organocatalytic domino Michael/aldol reaction is presented. The reaction is catalyzed by chiral amines and gives access to highly functionalized cyclohexanes with one all-carbon quaternary stereocenter and multiple chiral stereocenters in high yields and 83–98% ee.

  提出了高度对映选择性的有机催化多米诺骨牌迈克尔/羟醛反应。该反应被手性胺催化，并以高收率和83-98％ee获得具有一个全碳四元立体中心和多个手性立体中心的高度官能化的环己烷。
• Stereoselective electrochemical transformation of alkylidenecyanoacetates and malonate into (E)-3-substituted-2-cyanocyclopropane-1,1,2-tricarboxylates
  作者：Michail N Elinson、Sergey K Feducovich、Zoya A Starikova、Olga S Olessova、Anatolii N Vereshchagin、Gennady I Nikishin

  DOI：10.1016/s0040-4039(00)00733-4

  日期：2000.6

  Electrolysis of malonate and alkylidenecyanoacetates in alcohols in the presence of sodium bromide in an undivided cell results in the stereoselective formation of (E)-3-substituted 2-cyanocyclopropane-1,1,2-tricarboxylates in 75-85% yields. (C) 2000 Elsevier Science Ltd. All rights reserved.