(3aS,7aR)-2-benzyloctahydroisoindol-1-one

• 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: (3aS,7aR)-2-benzyloctahydroisoindol-1-one
• 英文别名: (3aS,7aR)-2-benzyl-3a,4,5,6,7,7a-hexahydro-3H-isoindol-1-one
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: QXGJOUACXOXZKX-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-benzylhexahydro-1H-isoindole-1,3(2H)-dione 在 三乙基硅烷 、 三氟化硼四氢呋喃络合物 、 chiral oxazaborolidine catalyst 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3aS,7aR)-2-benzyloctahydroisoindol-1-one
  参考文献：
  名称：

  Efficient desymmetrisation of a meso-imide using a chiral oxazaborolidine catalyst

  摘要：

  Desymmetrisation of a meso-imide by enantioselective reduction using a chiral oxazaborolidine catalyst derived from (1R,2S)-cis-1-amino-2-indanol followed by reduction of the hydroxylactam product proceeded with good enantiomeric excess (80-91%) at significantly lower catalyst loadings compared to reactions using the prolinol-derived catalyst. Models for the selectivity observed are proposed based upon structural probes and experimental observations. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00248-3

文献信息

• The crucial role of the nitrogen substituent in the desymmetrisation of cyclic meso-imides using B-Me and B-OMe oxazaborolidine catalysts
  作者：Mike D. Barker、Rachel A. Dixon、Simon Jones、Barrie J. Marsh

  DOI：10.1016/j.tet.2006.09.051

  日期：2006.12

  Various cyclic meso-imides have been desymmetrised via enantioselective reduction using two chiral oxazaborolidine catalysts derived from (1R,2S)-cis-1-amino-indan-2-ol followed by the reduction of the hydroxylactarn product to give the gamma-lactam. The enantiomeric excesses were shown to be 27-99% by chiral HPLC and chiral GC of the gamma-lactam products with the nitrogen substituent playing a pivotal role in determining yield and selectivity. (c) 2006 Elsevier Ltd. All rights reserved.
• BRETTLE, R.;SHIBIB, SAAD, M., J. CHEM. SOC. PERKIN TRANS., 1981, N 11, 2912-2919
  作者：BRETTLE, R.、SHIBIB, SAAD, M.

  DOI：——

  日期：——
• Efficient desymmetrisation of a meso-imide using a chiral oxazaborolidine catalyst
  作者：Rachel A. Dixon、Simon Jones

  DOI：10.1016/s0957-4166(02)00248-3

  日期：2002.6

  Desymmetrisation of a meso-imide by enantioselective reduction using a chiral oxazaborolidine catalyst derived from (1R,2S)-cis-1-amino-2-indanol followed by reduction of the hydroxylactam product proceeded with good enantiomeric excess (80-91%) at significantly lower catalyst loadings compared to reactions using the prolinol-derived catalyst. Models for the selectivity observed are proposed based upon structural probes and experimental observations. (C) 2002 Elsevier Science Ltd. All rights reserved.