[(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2Z)-ylidene]-nitro-acetic acid ethyl ester | 157825-36-0

• 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: [(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2Z)-ylidene]-nitro-acetic acid ethyl ester
• 英文别名: ethyl (2Z)-2-[(5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]pyrrolidin-2-ylidene]-2-nitroacetate
• CAS: 157825-36-0
• 化学式: C₂₅H₃₂N₂O₅Si
• 分子量: 468.625
• InChiKey: PXJPKEOHTMGIQW-VLZBMTSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2Z)-ylidene]-nitro-acetic acid ethyl ester 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 碳酸氢钠 、 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 ℃ 、506.62 kPa 条件下， 生成 (2,2-Dimethyl-propionylamino)-[(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
• 作为产物：
  描述：

  (5R)-5-[[[叔丁基二苯基硅基]氧]甲基]-2-吡咯烷酮 以 苯 为溶剂， 生成 [(R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2Z)-ylidene]-nitro-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

文献信息

• Synthesis, chemical property, and cytotoxicity of the carzinophilin congeners carrying a 2-(1-acylamino-1-alkoxycarbonyl)methylidene-1-azabicyclo[3.1.0]hexane system
  作者：Masaru Hashimoto、Miyoko Matsumoto、Kaoru Yamada、Shiro Terashima

  DOI：10.1016/s0040-4039(00)76798-0

  日期：1994.4

  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.