苯乙酰腈,a-2-亚丙烯基- | 13654-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯乙酰腈,a-2-亚丙烯基-
• 英文名称: 2-phenyl-penta-2,4-dienenitrile
• 英文别名: 2-phenyl-2,4-pentadienenitrile；2-Phenylpenta-2,4-dienenitrile
• CAS: 13654-20-1
• 化学式: C₁₁H₉N
• 分子量: 155.199
• InChiKey: UJXSBQBSARSVJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  苯乙酰腈,a-2-亚丙烯基- 在 甲醇 、 bis(1,5-cyclooctadiene)nickel (0) 、 1,3-双(二苯基膦)丙烷 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 5.5h， 生成 3-甲基-5-苯基吡啶
  参考文献：
  名称：

  Direct access to pentenedinitriles via Ni-catalyzed dihydrocyanation of 1,3-enynes

  摘要：

  1,3-烯烃的高区域和立体选择性二氢氰化反应由镍/二膦催化剂实现。

  DOI：

  10.1039/d0cc02938f
• 作为产物：
  描述：

  苯乙酰胺,N-2-炔丙基- 在 四氯化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以56%的产率得到苯乙酰腈,a-2-亚丙烯基-
  参考文献：
  名称：

  Rearrangements of Substituted 3-Aza-1,2,5-hexatrienes. 3. The Scope and Versatility of an Extremely Mild 3-Aza-Cope Reaction

  摘要：

  An investigation of the [3,3]-sigmatropic reaction of substituted 3-aza-1,2,5-hexatrienes to give 4-pentenenitriles is presented. This reaction has been found to occur under a wide variety of reactions conditions (10 are reported) starting from readily available N-allylamides. In contrast to other 3-aza-Cope reactions, this process occurs at room temperature, under essentially neutral conditions, allowing for the facile preparation of substituted nitrile products in moderate to excellent yields. The scope and versatility of this reaction are demonstrated by its use on a wide variety of substrates, including nitrogen- and oxygen-substituted amides. The rearrangements of cis- and trans-4-tert-butyl-N-allylcyclohexanecarboxamides 16a and 16b are reported and were found to give a ratio of axial to equatorial (A:E) products consistent with A:E ratios found for other related sigmatropic reactions. The stereochemical requirements for this reaction appear to be similar to other [3,3]-rearrangements even though the transition state for this rearrangement is most likely neither boat nor chairlike.

  DOI：

  10.1021/jo951587g

文献信息

• Generation and Reaction of Ammonium Ylides in Basic Two-Phase Systems
  作者：Anna Kowalkowska、Dorota Sucho?biak、Andrzej Jo?czyk

  DOI：10.1002/ejoc.200400556

  日期：2005.3

  Reaction of the quaternary ammonium salts 2a–i with electrophilic alkenes 3, active alkylating agents 7 or aromatic aldehydes 11, carried out in basic two-phase systems A–D, afforded cyclopropanes 4, cyanoalkenes 8 or cyanooxiranes 12 respectively, via the corresponding ammonium ylides 2+ –. The method is very simple, and gives cyclopropanes 4 and cyanoalkenes 8 in high yield. Under similar conditions

  季铵盐 2a-i 与亲电烯烃 3、活性烷化剂 7 或芳香醛 11 在碱性两相​​体系 A-D 中进行反应，通过相应的铵分别得到环丙烷 4、氰基烯烃 8 或氰基环氧乙烷 12叶立德 2+ -。该方法非常简单，可以高收率得到环丙烷4和氰基烯烃8。在类似条件下，1-氰基二烯 8aa,ba 在 γ,δ-双键处发生环丙烷化，形成乙烯基环丙烷 9a,b。从文献、1H NMR 光谱数据、NOE 实验或 X 射线单晶分析中阐明了制备的环丙烷的立体化学。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Generation and Reactions of Ammonium Ylides in Basic Two-Phase Systems: Convenient Synthesis of Cyclopropanes, Oxiranes and Alkenes Substituted with Electron-Withdrawing Groups
  作者：Andrzej Jończyk、Anna Konarska

  DOI：10.1055/s-1999-2757

  日期：1999.7
• Direct access to pentenedinitriles <i>via</i> Ni-catalyzed dihydrocyanation of 1,3-enynes
  作者：Feilong Sun、Jihui Gao、Xianjie Fang

  DOI：10.1039/d0cc02938f

  日期：——

  A highly regio- and stereoselective dihydrocyanation of 1,3-enynes was implemented by nickel/diphosphine catalysts.

  1,3-烯烃的高区域和立体选择性二氢氰化反应由镍/二膦催化剂实现。
• Rearrangements of Substituted 3-Aza-1,2,5-hexatrienes. 3. The Scope and Versatility of an Extremely Mild 3-Aza-Cope Reaction
  作者：Michael A. Walters、Andrew B. Hoem、Colleen S. McDonough

  DOI：10.1021/jo951587g

  日期：1996.1.1

  An investigation of the [3,3]-sigmatropic reaction of substituted 3-aza-1,2,5-hexatrienes to give 4-pentenenitriles is presented. This reaction has been found to occur under a wide variety of reactions conditions (10 are reported) starting from readily available N-allylamides. In contrast to other 3-aza-Cope reactions, this process occurs at room temperature, under essentially neutral conditions, allowing for the facile preparation of substituted nitrile products in moderate to excellent yields. The scope and versatility of this reaction are demonstrated by its use on a wide variety of substrates, including nitrogen- and oxygen-substituted amides. The rearrangements of cis- and trans-4-tert-butyl-N-allylcyclohexanecarboxamides 16a and 16b are reported and were found to give a ratio of axial to equatorial (A:E) products consistent with A:E ratios found for other related sigmatropic reactions. The stereochemical requirements for this reaction appear to be similar to other [3,3]-rearrangements even though the transition state for this rearrangement is most likely neither boat nor chairlike.