3-(2-氰基甲基苯基)丙腈 | 16061-73-7

• 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: 3-(2-氰基甲基苯基)丙腈
• 英文名称: 3-(2-cyanomethylphenyl)propionitrile
• 英文别名: 3-propionitril；3-[2-(Cyanomethyl)phenyl]propanenitrile
• CAS: 16061-73-7
• 化学式: C₁₁H₁₀N₂
• mdl: MFCD09923666
• 分子量: 170.214
• InChiKey: FVBBHBKNBNHLGD-UHFFFAOYSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  363.8±22.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-氰基甲基苯基)丙腈 在 硫酸 作用下， 生成 3-[2-(羧甲基)苯基]丙酸
  参考文献：
  名称：

  The degenerate side chain approach to the carbon analog of the Claisen rearrangement. Formation of nine-membered rings by a sterically accelerated ene reaction

  摘要：

  DOI：

  10.1021/ja00501a026
• 作为产物：
  描述：

  邻溴氰苄 、 丙烯腈 在 乙醇 、 nickel dibromide 四丁基溴化铵 、 四丁基碘化铵 、 1,2-二溴乙烷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 以62%的产率得到3-(2-氰基甲基苯基)丙腈
  参考文献：
  名称：

  Synthesis of functionalized benzannulated compounds

  摘要：

  Functionalized indane and naphthalene derivatives have been prepared according to two routes involving a nickel-catalyzed electrochemical arylation of activated olefins as the key step. The first method is a cascade process including the intramolecular nucleophilic addition of the first formed enolate intermediate. In the second method the cascade reaction is prevented by in situ protonation of the enolate, and the cyclization is further conducted chemically. This is an overall more efficient method than the first one, based on the electrochemical process. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.098

文献信息

• Quinazolines. V. Synthesis and proof of structure of 1,3-diamino-5,6-dihydrobenzo[f]quinazoline
  作者：Elizabeth P. Burrows、Andre Rosowsky、Edward J. Modest

  DOI：10.1021/jo01287a094

  日期：1967.12
• The degenerate side chain approach to the carbon analog of the Claisen rearrangement. Formation of nine-membered rings by a sterically accelerated ene reaction
  作者：Joseph B. Lambert、Dietrich M. Fabricius、James J. Napoli

  DOI：10.1021/ja00501a026

  日期：1979.3
• Synthesis of functionalized benzannulated compounds
  作者：Sylvie Condon、Amane El Ouarradi、Estelle Métay、Eric Léonel、Maryse Bourdonneau、Jean-Yves Nédélec

  DOI：10.1016/j.tet.2008.07.098

  日期：2008.9

  Functionalized indane and naphthalene derivatives have been prepared according to two routes involving a nickel-catalyzed electrochemical arylation of activated olefins as the key step. The first method is a cascade process including the intramolecular nucleophilic addition of the first formed enolate intermediate. In the second method the cascade reaction is prevented by in situ protonation of the enolate, and the cyclization is further conducted chemically. This is an overall more efficient method than the first one, based on the electrochemical process. (C) 2008 Elsevier Ltd. All rights reserved.