N-(2-cyanocyclohex-1-en-1-yl)acetamide | 500896-58-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-cyanocyclohex-1-en-1-yl)acetamide
• 英文别名: 2-acetylamino-1-cyclohexene-1-carbonitrile；N-(2-Cyano-cyclohex-1-enyl)-acetamide；N-(2-cyanocyclohexen-1-yl)acetamide
• CAS: 500896-58-2
• 化学式: C₉H₁₂N₂O
• 分子量: 164.207
• InChiKey: NJAAKBJNTCGTOC-UHFFFAOYSA-N

物化性质

• 沸点：
  363.6±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-cyanocyclohex-1-en-1-yl)acetamide 、 mesityl(phenyl)iodonium triflouromethanesulfonate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙酸乙酯 为溶剂， 以47%的产率得到(Z)-2-methyl-N-phenyl-5,6,7,8-tetrahydro-4H-benzo[d][1,3]oxazin-4-imine
  参考文献：
  名称：

  铜催化的邻氰基苯胺与高价碘鎓盐的氧化环封闭：氨基苯并恶嗪的芳基环封闭方法

  摘要：

  AbstractA novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho‐cyanoanilides and diaryliodonium triflates via an oxidative arylation–cyclization path. The reaction is supposed to involve the formation of highly active aryl‐copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2‐dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2–16 h.magnified image

  DOI：

  10.1002/adsc.201400763
• 作为产物：
  描述：

  1,5-二氰基戊烷 在 吡啶 、 potassium tert-butylate 作用下， 反应 16.0h， 生成 N-(2-cyanocyclohex-1-en-1-yl)acetamide
  参考文献：
  名称：

  Rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles

  摘要：

  The rhodium-catalyzed asymmetric hydrogenation of beta-acetylamino acrylonitriles was investigated by using monophosphine and bisphosphine ligands. It was found that an Rh-QuinoxP* complex exhibited high enantioselectivities for beta-aryl substituted beta-acetylamino acrylonitriles and the Rh-JosiPhos CyPF-t-Bu complex was proven to be effective for the hydrogenation of tetrasubstituted olefins from cyclic beta-acetylamino acrylonitriles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.023

文献信息

• Rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles
  作者：Miaofeng Ma、Guohua Hou、Junru Wang、Xumu Zhang

  DOI：10.1016/j.tetasy.2011.01.023

  日期：2011.3

  The rhodium-catalyzed asymmetric hydrogenation of beta-acetylamino acrylonitriles was investigated by using monophosphine and bisphosphine ligands. It was found that an Rh-QuinoxP* complex exhibited high enantioselectivities for beta-aryl substituted beta-acetylamino acrylonitriles and the Rh-JosiPhos CyPF-t-Bu complex was proven to be effective for the hydrogenation of tetrasubstituted olefins from cyclic beta-acetylamino acrylonitriles. (C) 2011 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Oxidative Ring Closure of<i>ortho</i>-Cyanoanilides with Hypervalent Iodonium Salts: Arylation-Ring Closure Approach to Iminobenzoxazines
  作者：Klára Aradi、Zoltán Novák

  DOI：10.1002/adsc.201400763

  日期：2015.2.9

  AbstractA novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho‐cyanoanilides and diaryliodonium triflates via an oxidative arylation–cyclization path. The reaction is supposed to involve the formation of highly active aryl‐copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2‐dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2–16 h.magnified image