(E)-1-<(S)-2-t-butyldimethylsiloxymethylpyrrolidin-1-yl>-2-nitropropene | 172095-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-1-<(S)-2-t-butyldimethylsiloxymethylpyrrolidin-1-yl>-2-nitropropene
• 英文别名: tert-butyl-dimethyl-[[(2S)-1-[(E)-2-nitroprop-1-enyl]pyrrolidin-2-yl]methoxy]silane
• CAS: 172095-08-8
• 化学式: C₁₄H₂₈N₂O₃Si
• 分子量: 300.473
• InChiKey: DCQRGAKBRAGFNV-XSNHNAGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-<(S)-2-t-butyldimethylsiloxymethylpyrrolidin-1-yl>-2-nitropropene 、 α-甲基-γ-丁内酯 在 正丁基锂 、 (i-Pr)NH 、 zinc(II) chloride 作用下， 生成 (S)-2-methyl-2-<(E)-2-nitropropenyl>-4-butanolide
  参考文献：
  名称：

  An Asymmetric Nitroolefination of α-Alkyl-γ-and δ-Lactones with Modified Nitroenamines

  摘要：

  New chiral nitroenamines 4a,b having (S)-2-t-butyldimethylsiloxymethylpyrrolidine as an auxiliary were found to be very effective for asymmetric nitroolefination of alpha-alkyl-gamma- and delta-lactones. The enantiomeric excess of the product increased remarkably in the reaction with gamma-lactones compared with previous nitroenamines 1a,b. A possible chelation model for the transition state of the asymmetric nitroolefination is discussed.

  DOI：

  10.1016/0040-4020(95)00683-y
• 作为产物：
  描述：

  L-脯氨醇 在 咪唑 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (E)-1-<(S)-2-t-butyldimethylsiloxymethylpyrrolidin-1-yl>-2-nitropropene
  参考文献：
  名称：

  An improved asymmetric nitroolefination of α-alkyl-γ- and δ-lactones with modified nitroenamines

  摘要：

  New chiral nitroenamines 4a, b were found to be very effective for asymmetric nitroolefination of alpha-alkyl-gamma- and delta-lactones. The enantiomeric excess of the product ran up to 99%. A possible chelation model for the transition state of the asymmetric nitroolefination was discussed.

  DOI：

  10.1016/0040-4039(94)02175-b

文献信息

• An Asymmetric Nitroolefination of α-Alkyl-γ-and δ-Lactones with Modified Nitroenamines
  作者：Kiyoharu Nishide、Ryuichi Kurosaki、Kouichi Hosomi、Hitoshi Imazato、Takehisa Inoue、Manabu Node、Toshiumi Ohmori、Kaoru Fuji

  DOI：10.1016/0040-4020(95)00683-y

  日期：1995.10

  New chiral nitroenamines 4a,b having (S)-2-t-butyldimethylsiloxymethylpyrrolidine as an auxiliary were found to be very effective for asymmetric nitroolefination of alpha-alkyl-gamma- and delta-lactones. The enantiomeric excess of the product increased remarkably in the reaction with gamma-lactones compared with previous nitroenamines 1a,b. A possible chelation model for the transition state of the asymmetric nitroolefination is discussed.
• An improved asymmetric nitroolefination of α-alkyl-γ- and δ-lactones with modified nitroenamines
  作者：Manabu Node、Ryuichi Kurosaki、Kouichi Hosomi、Takehisa Inoue、Kiyoharu Nishide、Toshiumi Ohmori、Kaoru Fuji

  DOI：10.1016/0040-4039(94)02175-b

  日期：1995.1

  New chiral nitroenamines 4a, b were found to be very effective for asymmetric nitroolefination of alpha-alkyl-gamma- and delta-lactones. The enantiomeric excess of the product ran up to 99%. A possible chelation model for the transition state of the asymmetric nitroolefination was discussed.