(S)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((1S,2R,3S,4S)-3-(4-methoxyphenyl)-2-methyl-4-nitrocyclobutyl)pyrrolidine | 1309664-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((1S,2R,3S,4S)-3-(4-methoxyphenyl)-2-methyl-4-nitrocyclobutyl)pyrrolidine
• CAS: 1309664-93-4
• 化学式: C₃₂H₄₀N₂O₄Si
• 分子量: 544.766
• InChiKey: CSDWPUQFODCNCQ-ZHQYQSJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  反式硝基苯乙烯 、 (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((1S,2R,3S,4S)-3-(4-methoxyphenyl)-2-methyl-4-nitrocyclobutyl)pyrrolidine 以 氘代甲苯 为溶剂， 生成 4-甲氧基-β-硝基苯乙烯 、 (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}-1-[(1S,2R,3S,4S)-2-methyl-4-nitro-3-phenylcyclobutyl]pyrrolidine
  参考文献：
  名称：

  Mechanistic Rationalization of Organocatalyzed Conjugate Addition of Linear Aldehydes to Nitro-olefins

  摘要：

  Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.

  DOI：

  10.1021/ja203660r
• 作为产物：
  描述：

  (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 4-甲氧基-β-硝基苯乙烯 、 丙醛 以 氘代甲苯 为溶剂， 生成 (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((1S,2R,3S,4S)-3-(4-methoxyphenyl)-2-methyl-4-nitrocyclobutyl)pyrrolidine
  参考文献：
  名称：

  Mechanistic Rationalization of Organocatalyzed Conjugate Addition of Linear Aldehydes to Nitro-olefins

  摘要：

  Kinetic studies of the conjugate addition of propanal to nitrostyrene catalyzed by diarylprolinol ethers reveal that formation of the product iminium species is rate-determining and is promoted by both the reaction product and acid additives. The beneficial role of a dominant cyclobutane intermediate in maintaining high stereoselectivity is highlighted. This mechanistic understanding led to the design of highly productive reaction protocols.

  DOI：

  10.1021/ja203660r