2-(cyclopropanecarbonyl)-3-methylbut-2-enenitrile | 1207895-47-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(cyclopropanecarbonyl)-3-methylbut-2-enenitrile
• CAS: 1207895-47-3
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: USFCPCHDHSHRST-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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反-1,3-戊二烯 、 2-(cyclopropanecarbonyl)-3-methylbut-2-enenitrile 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以64%的产率得到1-(cyclopropanecarbonyl)-2,6,6-trimethylcyclohex-3-ene-1-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
• 作为产物：
  描述：

  3-环丙基-3-氧代丙腈 、 丙酮 在 溶剂黄146 、 β-丙氨酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 2-(cyclopropanecarbonyl)-3-methylbut-2-enenitrile
  参考文献：
  名称：

  Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of β′-Acetoxy Allenoate: Highly Stereoselective Access to 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine

  摘要：

  Two classes of phosphine-catalyzed addition/cycloaddition domino reactions of beta'-acetoxy allenoate 1 have been developed. The reaction of 1 with 2-acyl-3-methyl-acrylonitrile 2 readily occurs to give 2-oxabicyclo[3.3.1]nonane 3, furnishing the beta'-addition/[4 + 4] cycloaddition domino sequence. In this sequence, beta'C of allenoate 1 is an electrophilic center, and its beta'C and gamma C serve as a 1,4-dipole. When the other reaction partner is switched to 2-acyl-3-(2-pyrrole)-acrylonitrile 8, a gamma-addition/[3 + 2] cycloaddition domino reaction is instead observed, in which allenoate 1 exhibits dual electrophilic reactivity of gamma C and 1,3-dipole chemical behavior of beta C and beta'C. Furthermore, both of these two asymmetric variants have also been achieved with up to 93% ee. The domino reactions presented in this report are valuable for highly stereoselective construction of complex structures under mild reaction conditions.

  DOI：

  10.1021/jacs.5b03273

文献信息

• 2,3-DIPHENYL-VALERONITRILDERIVATE, VERFAHREN ZU DEREN HERSTELLUNG UND DEREN VERWENDUNG ALS HERBIZIDE UND PFLANZENWACHSTUMSREGULATOREN
  申请人：Bayer Intellectual Property GmbH

  公开号：EP2731933B1

  公开（公告）日：2015-09-30