(1S,2R,5S,6S,7R)-4-benzyl-5-ethoxy-10-oxa-4-azatricyclo<5.2.1.0>decan-3-one | 155397-96-9

• 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: (1S,2R,5S,6S,7R)-4-benzyl-5-ethoxy-10-oxa-4-azatricyclo<5.2.1.0>decan-3-one
• 英文别名: (3S,3aS,4R,7S,7aR)-2-benzyl-3-ethoxy-3a,4,5,6,7,7a-hexahydro-3H-4,7-epoxyisoindol-1-one
• CAS: 155397-96-9
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: VZVBXKCZDRVMKW-SVZOTFJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S,6S,7R)-4-benzyl-5-ethoxy-10-oxa-4-azatricyclo<5.2.1.0>decan-3-one 、 烯丙基三甲基硅烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(1S,2R,5R,6S,7R)-5-allyl-4-benzyl-10-oxa-4-azatricyclo<5.2.1.0>decan-3-one
  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：

  norcantharidin 在 硼烷四氢呋喃络合物 、 硫酸 、 乙酰氯 、 (S)-CBS 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (1S,2R,5S,6S,7R)-4-benzyl-5-ethoxy-10-oxa-4-azatricyclo<5.2.1.0>decan-3-one
  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 catalyzed enantioselective reductions of cyclic meso-imides
  作者：Romeo Romagnoli、Eric C. Roos、Henk Hiemstra、Marinus J. Moolenaar、W. Nico Speckamp、Bernard Kaptein、Hans E. Schoemaker

  DOI：10.1016/s0040-4039(00)79972-2

  日期：1994.2

  A new asymmetric reduction method for meso-imides is reported. Treatment of various imides with a mixture of a chiral oxazaborolidine and BH3 leads 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 75-89% by both chiral HPLC-determinations and conversion of the reduction products into the corresponding, known lactones.