tert-Butoxycarbonylamino-[(R)-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester | 157825-46-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: tert-Butoxycarbonylamino-[(R)-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester
• CAS: 157825-46-2
• 化学式: C₁₅H₂₆N₂O₇S
• 分子量: 378.447
• InChiKey: PSIPUHPGESLREI-PJSNMCHCSA-N

物化性质

• 熔点：
  121-123 °C(Solvent: Diisopropyl ether)
• 沸点：
  524.9±50.0 °C(predicted)
• 密度：
  1.234±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-Butoxycarbonylamino-[(R)-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以56%的产率得到(1S,5R)-1-Aza-bicyclo[3.1.0]hex-(2E)-ylidene-tert-butoxycarbonylamino-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis, chemical property, and cytotoxicity of the carzinophilin congeners carrying a 2-(1-acylamino-1-alkoxycarbonyl)methylidene-1-azabicyclo[3.1.0]hexane system

  摘要：

  Synthesis of the title compounds was achieved by employing condensation of the 2-methoxy-1-pyrroline with ethyl nitroacetate and construction of 1-azabicyclo[3.1.0]hexane systems from 5-mesyloxymethylpyrrolidines as key steps. Some of these congeners which carry a C-6-C-11 unit involving the naphthalene part, were found to exhibit prominent cytotoxicity and effectively alkylate nucleophiles at both the aziridine and epoxide moieties.

  DOI：

  10.1016/s0040-4039(00)76798-0
• 作为产物：
  描述：

  (R)-2-(tert-butyldiphenylsiloxymethyl)-5-methoxy-3,4-dihydro-2H-pyrrole 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~60.0 ℃ 、506.62 kPa 条件下， 生成 tert-Butoxycarbonylamino-[(R)-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis, chemical property, and cytotoxicity of the carzinophilin congeners carrying a 2-(1-acylamino-1-alkoxycarbonyl)methylidene-1-azabicyclo[3.1.0]hexane system

  摘要：

  Synthesis of the title compounds was achieved by employing condensation of the 2-methoxy-1-pyrroline with ethyl nitroacetate and construction of 1-azabicyclo[3.1.0]hexane systems from 5-mesyloxymethylpyrrolidines as key steps. Some of these congeners which carry a C-6-C-11 unit involving the naphthalene part, were found to exhibit prominent cytotoxicity and effectively alkylate nucleophiles at both the aziridine and epoxide moieties.

  DOI：

  10.1016/s0040-4039(00)76798-0