di-tert-butyl (1S,2S,4S,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate | 1379471-57-4

• 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: di-tert-butyl (1S,2S,4S,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate
• 英文别名: ditert-butyl (1S,2S,4S,5R,6S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]bicyclo[3.1.0]hexane-2,6-dicarboxylate
• CAS: 1379471-57-4
• 化学式: C₂₂H₃₇NO₆
• 分子量: 411.539
• InChiKey: FBGCZFZMYZYJLX-JDBKVLKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (1S,2S,5R,6S)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-methylenebicyclo[3.1.0]hexane-2,6-dicarboxylate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、1.38 MPa 条件下， 以74%的产率得到di-tert-butyl (1S,2S,4S,5R,6S)-2-tert-butoxycarbonylamino-4-methyl-bicyclo[3.1.0]hexane-2,6-dicarboxylate
  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.