(2S)-1-tert-butoxycarbonyl-2-[(trans-(2S,5S)-2,5-dimethyl-1-pyrrolidinyl)carbonyl]pyrrolidine | 409339-93-1

• 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: (2S)-1-tert-butoxycarbonyl-2-[(trans-(2S,5S)-2,5-dimethyl-1-pyrrolidinyl)carbonyl]pyrrolidine
• 英文别名: tert-butyl (2S)-2-[(2S,5S)-2,5-dimethylpyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate
• CAS: 409339-93-1
• 化学式: C₁₆H₂₈N₂O₃
• 分子量: 296.41
• InChiKey: MDKLPJXNANUBNX-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-1-tert-butoxycarbonyl-2-[(trans-(2S,5S)-2,5-dimethyl-1-pyrrolidinyl)carbonyl]pyrrolidine 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (2S)-2-[(trans-(2S,5S)-2,5-dimethyl-1-pyrrolidinyl)methyl]pyrrolidine
  参考文献：
  名称：

  New Catalysts for the Base-Promoted Isomerization of Epoxides to Allylic Alcohols. Broadened Scope and Near-Perfect Asymmetric Induction

  摘要：

  Optically active (1S,3R,4R)-3-[N-(trans-2,5-dialkyl)pyrrolidinyl]methyl-2-azabicyclo-[2.2.1]heptanes were evaluated as catalysts for the enantioselective beta-elimination of meso-epoxides. The (2R,5R)-dimethylpyrrolidinyl-substituted catalyst 4 exhibited exceptionally high enantioselectivity and reactivity, and several substrates were rearranged with enantioselectivities of 98-99% ee. In addition, the use of 4 allowed the first successful, true catalytic rearrangement of the difficult substrates cyclopentene oxide (81%, 96% ee) and (Z)-4-octene oxide (80%, 91% ee).

  DOI：

  10.1021/jo010934l
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 (2S,5S)-2,5-二甲基吡咯烷盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到(2S)-1-tert-butoxycarbonyl-2-[(trans-(2S,5S)-2,5-dimethyl-1-pyrrolidinyl)carbonyl]pyrrolidine
  参考文献：
  名称：

  New Catalysts for the Base-Promoted Isomerization of Epoxides to Allylic Alcohols. Broadened Scope and Near-Perfect Asymmetric Induction

  摘要：

  Optically active (1S,3R,4R)-3-[N-(trans-2,5-dialkyl)pyrrolidinyl]methyl-2-azabicyclo-[2.2.1]heptanes were evaluated as catalysts for the enantioselective beta-elimination of meso-epoxides. The (2R,5R)-dimethylpyrrolidinyl-substituted catalyst 4 exhibited exceptionally high enantioselectivity and reactivity, and several substrates were rearranged with enantioselectivities of 98-99% ee. In addition, the use of 4 allowed the first successful, true catalytic rearrangement of the difficult substrates cyclopentene oxide (81%, 96% ee) and (Z)-4-octene oxide (80%, 91% ee).

  DOI：

  10.1021/jo010934l

文献信息

• New Catalysts for the Base-Promoted Isomerization of Epoxides to Allylic Alcohols. Broadened Scope and Near-Perfect Asymmetric Induction
  作者：Sophie K. Bertilsson、Mikael J. Södergren、Pher G. Andersson

  DOI：10.1021/jo010934l

  日期：2002.3.1

  Optically active (1S,3R,4R)-3-[N-(trans-2,5-dialkyl)pyrrolidinyl]methyl-2-azabicyclo-[2.2.1]heptanes were evaluated as catalysts for the enantioselective beta-elimination of meso-epoxides. The (2R,5R)-dimethylpyrrolidinyl-substituted catalyst 4 exhibited exceptionally high enantioselectivity and reactivity, and several substrates were rearranged with enantioselectivities of 98-99% ee. In addition, the use of 4 allowed the first successful, true catalytic rearrangement of the difficult substrates cyclopentene oxide (81%, 96% ee) and (Z)-4-octene oxide (80%, 91% ee).