(1-chloro-2-propenylidene)cyclohexane | 386278-63-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (1-chloro-2-propenylidene)cyclohexane
• 英文别名: (2-Chloro-allylidene)cyclohexane；2-chloroprop-2-enylidenecyclohexane
• CAS: 386278-63-3
• 化学式: C₉H₁₃Cl
• 分子量: 156.655
• InChiKey: RZPHHAHHYZKBKC-UHFFFAOYSA-N

物化性质

• 沸点：
  221.1±9.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  N-甲基苯胺 、 (1-chloro-2-propenylidene)cyclohexane 在 tris(dibenzylideneacetone)dipalladium (0) sodium t-butanolate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以95%的产率得到N-(3-cyclohexylideneprop-1-en-2-yl)-N-methylaniline
  参考文献：
  名称：

  Palladium catalyzed amination of vinyl chlorides: a new entry to imines, enamines and 2-amino-1,3-butadienes

  摘要：

  在钯催化的与胺的交叉偶联反应中，首次使用了氯乙烯来生成亚胺和烯胺。这种新方法被应用于 2-氨基-1,3-丁二烯的合成，而相应的溴化物则无法实现这种合成。

  DOI：

  10.1039/b403655g
• 作为产物：
  描述：

  炔环己醇 在 吡啶 、 4-二甲氨基吡啶 、 palladium diacetate 、 二异丙胺 、 lithium chloride 、 copper(I) bromide 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 (1-chloro-2-propenylidene)cyclohexane
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x

文献信息

• Gold Catalysis: Evidence for the In-situ Reduction of Gold(III) During the Cyclization of Allenyl Carbinols
  作者：A. Stephen K. Hashmi、M. Carmen Blanco、Dirk Fischer、Jan W. Bats

  DOI：10.1002/ejoc.200600009

  日期：2006.3

  Products of an oxidative coupling were obtained in the gold(III)-catalyzed cycloisomerization of tertiary allenyl carbinols. The absence of reduced organic products and an increase of these coupling products with the amount of gold(III) catalyst suggests that gold(III) is reduced in situ, possibly to gold(I) catalysts which were also shown to be active for these transformations. (© Wiley-VCH Verlag

  在金 (III) 催化的叔烯醇环异构化中获得氧化偶联产物。不存在还原的有机产物以及这些偶联产物随金 (III) 催化剂量的增加表明金 (III) 原位还原，可能还原为金 (I) 催化剂，其也显示出对这些转化具有活性. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (<i>Z</i>,<i>E</i>)-2-Bromo-1,3-dienes
  作者：Attila Horváth、Jan-E. Bäckvall

  DOI：10.1021/jo015950x

  日期：2001.11.1

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.
• Palladium catalyzed amination of vinyl chlorides: a new entry to imines, enamines and 2-amino-1,3-butadienes
  作者：José Barluenga、M. Alejandro Fernández、Fernando Aznar、Carlos Valdés

  DOI：10.1039/b403655g

  日期：——

  Vinyl chlorides are employed for the first time in palladium catalyzed cross-coupling reactions with amines to furnish imines and enamines. The new methodology has been applied to the synthesis of 2-amino-1,3-butadienes, that could not be achieved from the corresponding bromides.

  在钯催化的与胺的交叉偶联反应中，首次使用了氯乙烯来生成亚胺和烯胺。这种新方法被应用于 2-氨基-1,3-丁二烯的合成，而相应的溴化物则无法实现这种合成。