3-phenyl-2-propionylbicyclo[2.2.2]oct-5-ene-2-carbonitrile

• 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: 3-phenyl-2-propionylbicyclo[2.2.2]oct-5-ene-2-carbonitrile
• 英文别名: (1R,2R,3S,4S)-3-phenyl-2-propanoylbicyclo[2.2.2]oct-5-ene-2-carbonitrile
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: OTUSEGRCBRTGEP-ATLSCFEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-2-benzylidene-3-oxopentanenitrile 、 1,3-环己二烯 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到3-phenyl-2-propionylbicyclo[2.2.2]oct-5-ene-2-carbonitrile
  参考文献：
  名称：

  Diels–Alder reactions of acyclic α-cyano α,β-alkenones: a new approach to highly substituted cyclohexene system

  摘要：

  The Diels-Alder reactions of a variety of acyclic a-cyano a,p-unsaturated ketones 8 have been investigated. With the assistance of boron trichloride, these compounds were found to undergo the cycloaddition readily with dienes to give the corresponding adducts 9 in good to high yields. In addition, some of 9 could be further subjected to the reductive alkylation reactions using lithium naphthalenide (LN) and an appropriate alkylating agent, thus allowing for the generation of highly substituted cyclohexenes 10 with the replacement of the cyano group with an alkyl substituent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.105

文献信息

• Diels–Alder reactions of acyclic α-cyano α,β-alkenones: a new approach to highly substituted cyclohexene system
  作者：Prashanth K. Amancha、Yi-Chun Lai、I.-Chia Chen、Hsing-Jang Liu、Jia-Liang Zhu

  DOI：10.1016/j.tet.2009.11.105

  日期：2010.1

  The Diels-Alder reactions of a variety of acyclic a-cyano a,p-unsaturated ketones 8 have been investigated. With the assistance of boron trichloride, these compounds were found to undergo the cycloaddition readily with dienes to give the corresponding adducts 9 in good to high yields. In addition, some of 9 could be further subjected to the reductive alkylation reactions using lithium naphthalenide (LN) and an appropriate alkylating agent, thus allowing for the generation of highly substituted cyclohexenes 10 with the replacement of the cyano group with an alkyl substituent. (C) 2009 Elsevier Ltd. All rights reserved.