(E)-2-[2'-cyano-3'-(trimethylsilyl)prop-2'-enyl]phthalimide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (E)-2-[2'-cyano-3'-(trimethylsilyl)prop-2'-enyl]phthalimide
• 英文别名: (E)-2-[(1,3-dioxoisoindol-2-yl)methyl]-3-trimethylsilylprop-2-enenitrile
• 化学式: C₁₅H₁₆N₂O₂Si
• 分子量: 284.39
• InChiKey: YJHIKERJSVEFBC-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-[2'-cyano-3'-(trimethylsilyl)prop-2'-enyl]phthalimide 在 Lindlar's catalyst 氢气 作用下， 以 乙酸乙酯 为溶剂， 70.0 ℃ 、999.74 kPa 条件下， 反应 16.0h， 以92%的产率得到2-(2'-cyano-3'-trimethylsilylpropyl)phthalimide
  参考文献：
  名称：

  A new enantioselective synthesis of β-amino acids

  摘要：

  Enantioselective hydrogenation of some alpha,beta -unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the alpha -carbon using Rh-DuPHOS catalysts afforded beta -amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the alpha,beta -unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00097-0
• 作为产物：
  描述：

  氢氰酸 、 N-[3-(三甲基硅基)-2-丙炔基]邻苯二甲酰亚胺 在 亚磷酸三苯酯 、 四(亚磷酸三苯酯)镍 作用下， 以 苯 为溶剂， 以70%的产率得到(E)-2-[2'-cyano-3'-(trimethylsilyl)prop-2'-enyl]phthalimide
  参考文献：
  名称：

  A new enantioselective synthesis of β-amino acids

  摘要：

  Enantioselective hydrogenation of some alpha,beta -unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the alpha -carbon using Rh-DuPHOS catalysts afforded beta -amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the alpha,beta -unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00097-0

文献信息

• A new enantioselective synthesis of β-amino acids
  作者：Dilek Saylik、Eva M. Campi、Andrew C. Donohue、W.Roy Jackson、Andrea J. Robinson

  DOI：10.1016/s0957-4166(01)00097-0

  日期：2001.3

  Enantioselective hydrogenation of some alpha,beta -unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the alpha -carbon using Rh-DuPHOS catalysts afforded beta -amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the alpha,beta -unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.