(Z)-4,4-dimethyl-2-phenylpent-2-enenitrile | 110327-47-4

• 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: (Z)-4,4-dimethyl-2-phenylpent-2-enenitrile
• 英文别名: Z-2-phenyl-3-tert-butylacrylonitrile
• CAS: 110327-47-4
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: JSQXNFBSJZAFFJ-FMIVXFBMSA-N

物化性质

• 沸点：
  120-122 °C(Press: 0.41 Torr)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (Z)-4,4-dimethyl-2-phenylpent-2-enenitrile 生成 1.1.2-Trimethyl-3-phenyl-cyclopropan-3-carbonsaeurenitril
  参考文献：
  名称：

  KUMAGAI TSUTOMU; SEGAWA TORU; ENDO ZEN-ICHIROU; MUKAI TOSHIO, TETRAHEDRON LETT., 27,(1986) N 51, 6225-6228

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙腈 、 特戊醛 在 氢氧化钾 作用下， 反应 0.17h， 以87%的产率得到(Z)-4,4-dimethyl-2-phenylpent-2-enenitrile
  参考文献：
  名称：

  Solvent-free condensation of arylacetonitrile with aldehydes

  摘要：

  The condensation of a series of arylacetonitriles with aldehydes can be carried out by mixing equivalent amounts of reagents with neat powdered KOH at room temperature for 3-60 min depending on the aldehyde steric hindrance. At higher temperature (110 degrees C), yields were generally higher and purity increased within very short reaction times (1-5 min). With pentamethylphenylacetonitrile, a phase transfer agent was necessary to give a satisfactory yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.040

文献信息

• Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions
  作者：Amreen K. Bains、Yadav Ankit、Debashis Adhikari

  DOI：10.1021/acs.orglett.1c00162

  日期：2021.3.19
• Direct Synthesis of α,β-Unsaturated Nitriles Catalyzed by Nonionic Superbases
  作者：Bosco A. D'Sa、Philip Kisanga、John G. Verkade

  DOI：10.1021/jo972343u

  日期：1998.6.1

  We report herein the use of 3-30 mol % of a new class of tricyclic strong nonionic Lewis bases P(MeNCH2CH2)(3)N and P(HNCH2CH2)(i-PrNCH2CH2)(2)N for the direct catalytic synthesis of a variety of functionalized alpha,beta-unsaturated nitriles in high yields from aldehydes and acetonitrile or benzyl cyanide at 40-50 degrees C. Evidence for a novel mechanistic pathway proposed for this reaction in a polar protic solvent such as methanol, and a nonpolar aprotic solvent such as benzene is also presented. Under these conditions, primary and secondary aliphatic aldehydes do not condense satisfactorily with acetonitrile to give the alpha,beta-unsaturated nitrile, and ketones do not condense with either benzyl cyanide or acetonitrile.
• Photoreaction of α-phenylcrotononitrile derivatives: the facile cyclopropane ring formation
  作者：Tsutomu Kumagai、Toru Segawa、Zen-Ichirou Endo、Toshio Mukai

  DOI：10.1016/s0040-4039(00)85438-6

  日期：1986.1
• Solvent-free condensation of arylacetonitrile with aldehydes
  作者：Régis Guillot、André Loupy、Abdelkrim Meddour、Michèle Pellet、Alain Petit

  DOI：10.1016/j.tet.2005.07.040

  日期：2005.10

  The condensation of a series of arylacetonitriles with aldehydes can be carried out by mixing equivalent amounts of reagents with neat powdered KOH at room temperature for 3-60 min depending on the aldehyde steric hindrance. At higher temperature (110 degrees C), yields were generally higher and purity increased within very short reaction times (1-5 min). With pentamethylphenylacetonitrile, a phase transfer agent was necessary to give a satisfactory yield. (c) 2005 Elsevier Ltd. All rights reserved.
• KUMAGAI TSUTOMU; SEGAWA TORU; ENDO ZEN-ICHIROU; MUKAI TOSHIO, TETRAHEDRON LETT., 27,(1986) N 51, 6225-6228
  作者：KUMAGAI TSUTOMU、 SEGAWA TORU、 ENDO ZEN-ICHIROU、 MUKAI TOSHIO

  DOI：——

  日期：——