(2aR,2bR,5aS,5bS)-2-Oxo-hexahydro-1-aza-cyclopropa[cd]indene-1,5a-dicarboxylic acid 1-tert-butyl ester 5a-methyl ester | 597540-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2aR,2bR,5aS,5bS)-2-Oxo-hexahydro-1-aza-cyclopropa[cd]indene-1,5a-dicarboxylic acid 1-tert-butyl ester 5a-methyl ester
• 英文别名: 7-O-tert-butyl 6-O-methyl (1S,2R,6S,9R)-8-oxo-7-azatricyclo[4.3.0.02,9]nonane-6,7-dicarboxylate
• CAS: 597540-83-5
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: YCMKXDISWMICDT-OFYUCFFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2aR,2bR,5aS,5bS)-2-Oxo-hexahydro-1-aza-cyclopropa[cd]indene-1,5a-dicarboxylic acid 1-tert-butyl ester 5a-methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (1S,2S,6R,7R)-2-tert-Butoxycarbonylamino-bicyclo[4.1.0]heptane-2,7-dicarboxylic acid
  参考文献：
  名称：

  Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives

  摘要：

  Efficient synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740: 1) and its structurally related analogs (-)-2 and (-)-3 has been accomplished starting with (1S,2R)-1-amino-2-hydroxycyclopentane- or cyclohexanecarboxylic acid (4 or 17) via an intramolecular cyclopropanation of alpha-diazo acetamide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01316-9
• 作为产物：
  描述：

  (1S,2S,6R,7R)-2-tert-Butoxycarbonylamino-bicyclo[4.1.0]heptane-2,7-dicarboxylic acid dimethyl ester 在 双(三甲基硅烷基)氨基钾 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(2aR,2bR,5aS,5bS)-2-Oxo-hexahydro-1-aza-cyclopropa[cd]indene-1,5a-dicarboxylic acid 1-tert-butyl ester 5a-methyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives

  摘要：

  Efficient synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740: 1) and its structurally related analogs (-)-2 and (-)-3 has been accomplished starting with (1S,2R)-1-amino-2-hydroxycyclopentane- or cyclohexanecarboxylic acid (4 or 17) via an intramolecular cyclopropanation of alpha-diazo acetamide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01316-9