(1S,2S,4S,5R,6S)-2-Amino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid | 1379471-55-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,4S,5R,6S)-2-Amino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid
• 英文别名: (1S,2S,4S,5R,6S)-2-amino-4-methylbicyclo[3.1.0]hexane-2,6-dicarboxylic acid
• CAS: 1379471-55-2
• 化学式: C₉H₁₃NO₄
• 分子量: 199.207
• InChiKey: BQVZICWQBFTOJX-DJBRRKJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  di-tert-butyl (1S,2S,4S,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate 在 甲烷磺酸 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 以77%的产率得到(1S,2S,4S,5R,6S)-2-Amino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid
  参考文献：
  名称：

  Improved Synthesis of C4α- and C4β-Methyl Analogues of 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylate

  摘要：

  An efficient and divergent synthesis of C4 alpha- and C4 beta-methyl-substituted analogues of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate, which are important tools in the study of metabotropic glutamate receptor function, has been achieved. By taking advantage of an unanticipated facial selectivity of the bicyclo[3.1.0]hexane ring system, either the C4 alpha- or C4 beta-methyl substituent was introduced In a highly stereoselective and high-yielding manner.

  DOI：

  10.1021/ol300516y

文献信息

• Improved Synthesis of C4α- and C4β-Methyl Analogues of 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylate
  作者：Steven S. Henry、Molly D. Brady、Dana L. T. Laird、J. Craig Ruble、David L. Varie、James A. Monn

  DOI：10.1021/ol300516y

  日期：2012.6.1

  An efficient and divergent synthesis of C4 alpha- and C4 beta-methyl-substituted analogues of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate, which are important tools in the study of metabotropic glutamate receptor function, has been achieved. By taking advantage of an unanticipated facial selectivity of the bicyclo[3.1.0]hexane ring system, either the C4 alpha- or C4 beta-methyl substituent was introduced In a highly stereoselective and high-yielding manner.