1-[(2E)-3-chloroprop-2-en-1-yl]piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-[(2E)-3-chloroprop-2-en-1-yl]piperidine
• 英文别名: (E)-1-(3-chloro-prop-2-enyl)-piperidine；[(2E)-3-chloroprop-2-en-1-yl]piperidine；((2E)-3-chloroprop-2-enyl)piperidine；1-[(E)-3-chloroprop-2-enyl]piperidine
• 化学式: C₈H₁₄ClN
• 分子量: 159.659
• InChiKey: BHUQRWSKYCJKDU-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  正丁基氯化镁 、 1-[(2E)-3-chloroprop-2-en-1-yl]piperidine 在 iron(III)-acetylacetonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 1.5h， 以80%的产率得到1-[(2E)-hept-2-en-1-yl]piperidine
  参考文献：
  名称：

  Stereoselective synthesis of allylamines by iron-catalyzed cross-coupling of 3-chloroprop-2-en-1-amines with grignard reagents. Synthesis of naftifine

  摘要：

  A general procedure for the synthesis of trans- and cis-allylamines has been developed on the basis of iron-catalyzed cross-coupling of Grignard reagents with stereochemically pure 3-chloroprop-2-en-1-amines prepared by allylation of amines with commercially available 1,3-dichloropropene isomers.

  DOI：

  10.1134/s1070428014030038
• 作为产物：
  描述：

  哌啶 、 反式-1,3-二氯-1-丙烯 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以89%的产率得到1-[(2E)-3-chloroprop-2-en-1-yl]piperidine
  参考文献：
  名称：

  Reactions of (E)- and (Z)-1,3-dichloropropenes with secondary amines

  摘要：

  An efficient procedure was developed for preparation of (E)- and (Z)-3-chloroprop-2-ne-1-ylamines from commercially available 1,3-dichloropropene.

  DOI：

  10.1134/s1070427211030293

文献信息

• Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature
  作者：Mouâd Alami、Benoit Crousse、Fabiola Ferri

  DOI：10.1016/s0022-328x(00)00909-8

  日期：2001.4

  Copper iodide and weakly ligated palladium complexes PdCl2(RCN)(2) (R = Ph, Me) catalyzed efficiently the coupling reaction of vinyl chlorides with 1-alkynes in the presence of piperidine to give the corresponding conjugated enynes in good to excellent yields. The reaction takes place rapidly and cleanly at room temperature. Application to the synthesis of terbinafine which exhibits strong antimycotic activity has been realized. (C) 2001 Elsevier Science B.V. All rights reserved.
• Pd-Cu-catalyzed synthesis of N-(2E,4)- and N-(2Z,4)-enyne cyclic amines
  作者：A. Sh. Sunagatullina、R. N. Shakhmaev、V. V. Zorin

  DOI：10.1134/s1070428013050163

  日期：2013.5

  By Pd-Cu-catalyzed coupling of (2E)- and (2Z)-3-chloroprop-2-en-1-ylamines and alkynes a stereoselective method of the synthesis was developed for a series of (2E,4)- and (2Z,4)-enyne cyclic amines.
• US6359174B1
  申请人：——

  公开号：US6359174B1

  公开（公告）日：2002-03-19
• Stereoselective synthesis of allylamines by iron-catalyzed cross-coupling of 3-chloroprop-2-en-1-amines with grignard reagents. Synthesis of naftifine
  作者：R. N. Shakhmaev、A. Sh. Sunagatullina、V. V. Zorin

  DOI：10.1134/s1070428014030038

  日期：2014.3

  A general procedure for the synthesis of trans- and cis-allylamines has been developed on the basis of iron-catalyzed cross-coupling of Grignard reagents with stereochemically pure 3-chloroprop-2-en-1-amines prepared by allylation of amines with commercially available 1,3-dichloropropene isomers.
• Reactions of (E)- and (Z)-1,3-dichloropropenes with secondary amines
  作者：A. U. Takhautdinova、E. R. Mindiyarova、R. N. Shakhmaev、V. V. Zorin

  DOI：10.1134/s1070427211030293

  日期：2011.3

  An efficient procedure was developed for preparation of (E)- and (Z)-3-chloroprop-2-ne-1-ylamines from commercially available 1,3-dichloropropene.