tert-butyl (1S,2S,5R)-2-(hydroxymethyl)-4-oxo-3-azabicyclo[3.1.0]hexane-3-carboxylate | 134419-21-9

• 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: tert-butyl (1S,2S,5R)-2-(hydroxymethyl)-4-oxo-3-azabicyclo[3.1.0]hexane-3-carboxylate
• CAS: 134419-21-9
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: VWRHEPAGKDNMPA-XLPZGREQSA-N

物化性质

• 沸点：
  390.1±15.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2S,5R)-2-(hydroxymethyl)-4-oxo-3-azabicyclo[3.1.0]hexane-3-carboxylate 在 lithium hydroxide 、 sodium hydroxide 、 jones reagent 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 19.5h， 生成 (2S,3S,4R)-α-(carboxycyclopropyl)glycine
  参考文献：
  名称：

  Shimamoto, Keiko; Ohfune, Yasufumi, Tetrahedron Letters, 1989, vol. 30, # 29, p. 3803 - 3804

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(tert-Butoxycarbonyl)-3-aza-4-(((tert-butyldimethylsilyl)oxy)methyl)bicyclo<3.1.0>hexan-2-one 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 tert-butyl (1S,2S,5R)-2-(hydroxymethyl)-4-oxo-3-azabicyclo[3.1.0]hexane-3-carboxylate
  参考文献：
  名称：

  Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs

  摘要：

  To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereomeric L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues of the extended and folded conformers of L-Glu, were synthesized and subjected to neutrophysiological assay. Compounds 1-4 were efficiently synthesized from chiral amino acids. Cyclopropanation of the (2S)-2-amino-3-butenol derivative 5b gave intermediates for the synthesis of all four diastereomers. Stereoselective cyclopropanation of both the alpha,beta-unsaturated gamma-lactam 16 and the delta-lactone 19 gave precursors of (2S,1'S,2'R)-3 and (2S,1'R,2'S)-4, respectively. Neurophysiological assays of 1-4 performed with the newborn rat spinal cord demonstrated that the compounds induced a variety of depolarizing effects. The results of the assays strongly suggested that the N-methyl-D-aspartic acid (NMDA) receptor is activated by the folded conformer of L-Glu and that the extended conformer of L-Glu activates the metabotropic L-Glu receptor. The four analogous D-2-(carboxycyclopropyl)glycines (D-1-D-4), which were synthesized from (2R)-5b, proved to be NMDA agonists.

  DOI：

  10.1021/jo00013a018