(2aR,2bR,4aS,4bS)-1-(4-Methoxy-benzyl)-2-oxo-hexahydro-1-aza-cyclopropa[cd]pentalene-4a-carboxylic acid methyl ester | 597540-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2aR,2bR,4aS,4bS)-1-(4-Methoxy-benzyl)-2-oxo-hexahydro-1-aza-cyclopropa[cd]pentalene-4a-carboxylic acid methyl ester
• 英文别名: methyl (1S,2R,5S,8R)-4-[(4-methoxyphenyl)methyl]-3-oxo-4-azatricyclo[3.3.0.02,8]octane-5-carboxylate
• CAS: 597540-60-8
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: FPFGZHWOVHAESW-LOUJCGABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2aR,2bR,4aS,4bS)-1-(4-Methoxy-benzyl)-2-oxo-hexahydro-1-aza-cyclopropa[cd]pentalene-4a-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydroxide 、 ammonium cerium(IV) nitrate 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 71.83h， 生成 (1S,2S,5R,6S)-2-氨基二环[3.1.0]己烷-2,6-二羧酸
  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：

  (2aR,4aS,6aR,6bS)-4-(4-Methoxy-benzyl)-3-oxo-3,4,5,6,6a,6b-hexahydro-2aH-1,2,4-triaza-cyclopenta[cd]pentalene-4a-carboxylic acid methyl ester 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 以100%的产率得到(2aR,2bR,4aS,4bS)-1-(4-Methoxy-benzyl)-2-oxo-hexahydro-1-aza-cyclopropa[cd]pentalene-4a-carboxylic acid 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

文献信息

• Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives
  作者：Yasufumi Ohfune、Takashi Demura、Seiji Iwama、Hiromi Matsuda、Kosuke Namba、Keiko Shimamoto、Tetsuro Shinada

  DOI：10.1016/s0040-4039(03)01316-9

  日期：2003.7

  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.