2-{(R)-4,4,4-Trifluoro-3-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-1-phenyl-butyl}-malonic acid diethyl ester | 432030-79-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-{(R)-4,4,4-Trifluoro-3-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-1-phenyl-butyl}-malonic acid diethyl ester
• 英文别名: diethyl 2-[(1R,3E)-4,4,4-trifluoro-3-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]imino-1-phenylbutyl]propanedioate
• CAS: 432030-79-0
• 化学式: C₂₃H₃₁F₃N₂O₅
• 分子量: 472.505
• InChiKey: CUODNKMIAKFNKW-LXNJAMRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-{(R)-4,4,4-Trifluoro-3-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-1-phenyl-butyl}-malonic acid diethyl ester 在 ammonium carbonate 、 甲酸 、 硫酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (S)-1-(3-Iodo-propyl)-4-phenyl-6-trifluoromethyl-3,4-dihydro-1H-pyridin-2-one
  参考文献：
  名称：

  Synthesis of Optically Active Trifluoromethylated Indolizidine Derivatives via Stereoselective Radical Cyclization

  摘要：

  Asymmetric Michael reaction of lithiated trifluoroacetone SAMP-hydrazone with alkylidenemalonates gave addition products stereoselectively. Hydrolyzed enantiomerically pure ketoacids were cyclized to dihydropyridinones. N-lodopropylation followed by radical cyclization gave optically active trifluoromethylated indolizidinones stereoselectively.

  DOI：

  10.1021/ol025792b
• 作为产物：
  描述：

  (S)-1-amino-2-(methoxymethyl)pyrrolidine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 生成 2-{(R)-4,4,4-Trifluoro-3-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-1-phenyl-butyl}-malonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of Optically Active Trifluoromethylated Indolizidine Derivatives via Stereoselective Radical Cyclization

  摘要：

  Asymmetric Michael reaction of lithiated trifluoroacetone SAMP-hydrazone with alkylidenemalonates gave addition products stereoselectively. Hydrolyzed enantiomerically pure ketoacids were cyclized to dihydropyridinones. N-lodopropylation followed by radical cyclization gave optically active trifluoromethylated indolizidinones stereoselectively.

  DOI：

  10.1021/ol025792b

文献信息

• Synthesis of Optically Active Trifluoromethylated Indolizidine Derivatives via Stereoselective Radical Cyclization
  作者：Takashi Okano、Masataka Fumoto、Takahiro Kusukawa、Makoto Fujita

  DOI：10.1021/ol025792b

  日期：2002.5.1

  Asymmetric Michael reaction of lithiated trifluoroacetone SAMP-hydrazone with alkylidenemalonates gave addition products stereoselectively. Hydrolyzed enantiomerically pure ketoacids were cyclized to dihydropyridinones. N-lodopropylation followed by radical cyclization gave optically active trifluoromethylated indolizidinones stereoselectively.