3-[(1S,3aS,7aR)-1-ethoxy-3-oxo-octahydroisoindol-2-yl]propionitrile | 192824-63-8

• 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: 3-[(1S,3aS,7aR)-1-ethoxy-3-oxo-octahydroisoindol-2-yl]propionitrile
• 英文别名: 3-[(1S,3aS,7aR)-1-ethoxy-3-oxo-3a,4,5,6,7,7a-hexahydro-1H-isoindol-2-yl]propanenitrile
• CAS: 192824-63-8
• 化学式: C₁₃H₂₀N₂O₂
• 分子量: 236.314
• InChiKey: XWORNHLOYMKTGY-LOWVWBTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(1S,3aS,7aR)-1-ethoxy-3-oxo-octahydroisoindol-2-yl]propionitrile 在 三氟化硼乙醚 、 calcium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 生成 3-[(1R,3aS,7aR)-1-allyl-3-oxo-octahydroisoindol-2-yl]propionitrile
  参考文献：
  名称：

  Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides

  摘要：

  Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00154-7
• 作为产物：
  描述：

  1,2-cis-cyclohexanedicarboxylic anhydride 在 硼烷四氢呋喃络合物 、 硫酸 、 (S)-CBS 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 生成 3-[(1S,3aS,7aR)-1-ethoxy-3-oxo-octahydroisoindol-2-yl]propionitrile
  参考文献：
  名称：

  Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides

  摘要：

  Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00154-7

文献信息

• Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides
  作者：Martin Ostendorf、Romeo Romagnoli、Isabel Cabeza Pereiro、Eric C. Roos、Marinus J. Moolenaar、W.Nico Speckamp、Henk Hiemstra

  DOI：10.1016/s0957-4166(97)00154-7

  日期：1997.6

  Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-alpha,alpha-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity. (C) 1997 Elsevier Science Ltd.