methyl (2R)-2-[(2R)-2-[(2S,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]pyrrolidin-1-yl]-3-hydroxy-3,3-diphenylpropanoate | 188429-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2R)-2-[(2R)-2-[(2S,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]pyrrolidin-1-yl]-3-hydroxy-3,3-diphenylpropanoate
• CAS: 188429-10-9
• 化学式: C₃₁H₄₃NO₆Si
• 分子量: 553.771
• InChiKey: QDRQXLPPAOWZBJ-LHWXFDGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[(2R)-2-[(2S,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]pyrrolidin-1-yl]-3-hydroxy-3,3-diphenylpropanoate 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到{(R)-2-[(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl]-pyrrolidin-1-yl}-acetic acid methyl ester
  参考文献：
  名称：

  An unexpected photoadduct of N-carbomethoxymethylpyrrolidine with a chiral butenolide and benzophenone: X-ray structure and synthetic utility

  摘要：

  The regio- and stereoselective photoinduced addition of N-carbomethoxymethylpyrrolidine to 5(S)-tert-butyldimethylsiloxymethyl-furan-2(5H)-one in the presence of benzophenone yields 3(R)-[N-(diphenylhydroxymethyl)carbo methoxymethylpyrrolidin-2'-yl]-4(S)-tert-butyldimethylsiloxymethyl)-butan-4-olides (epimeric at C-2'), and we report the X-ray structure of the major adduct together with its conversion into the 1-azabicyclo[4.3.0]-nonane ring system. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01057-5
• 作为产物：
  描述：

  二苯甲酮 、 2-(1-吡咯烷基)乙酸甲酯 、 (5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one 以 乙腈 为溶剂， 反应 24.0h， 生成 、 {(R)-2-[(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl]-pyrrolidin-1-yl}-acetic acid methyl ester 、 methyl (2R)-2-[(2R)-2-[(2S,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]pyrrolidin-1-yl]-3-hydroxy-3,3-diphenylpropanoate 、 methyl (2R)-2-[(2S)-2-[(2S,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-oxooxolan-3-yl]pyrrolidin-1-yl]-3-hydroxy-3,3-diphenylpropanoate
  参考文献：
  名称：

  An unexpected photoadduct of N-carbomethoxymethylpyrrolidine with a chiral butenolide and benzophenone: X-ray structure and synthetic utility

  摘要：

  The regio- and stereoselective photoinduced addition of N-carbomethoxymethylpyrrolidine to 5(S)-tert-butyldimethylsiloxymethyl-furan-2(5H)-one in the presence of benzophenone yields 3(R)-[N-(diphenylhydroxymethyl)carbo methoxymethylpyrrolidin-2'-yl]-4(S)-tert-butyldimethylsiloxymethyl)-butan-4-olides (epimeric at C-2'), and we report the X-ray structure of the major adduct together with its conversion into the 1-azabicyclo[4.3.0]-nonane ring system. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01057-5

文献信息

• An unexpected photoadduct of N-carbomethoxymethylpyrrolidine with a chiral butenolide and benzophenone: X-ray structure and synthetic utility
  作者：Elson Santiago de Alvarenga、Christine J. Cardin、John Mann

  DOI：10.1016/s0040-4020(96)01057-5

  日期：1997.1

  The regio- and stereoselective photoinduced addition of N-carbomethoxymethylpyrrolidine to 5(S)-tert-butyldimethylsiloxymethyl-furan-2(5H)-one in the presence of benzophenone yields 3(R)-[N-(diphenylhydroxymethyl)carbo methoxymethylpyrrolidin-2'-yl]-4(S)-tert-butyldimethylsiloxymethyl)-butan-4-olides (epimeric at C-2'), and we report the X-ray structure of the major adduct together with its conversion into the 1-azabicyclo[4.3.0]-nonane ring system. (C) 1997, Elsevier Science Ltd.