(3E,5R)-3-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]imino-5-(2-methylpropyl)oxolan-2-one | 204511-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3E,5R)-3-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]imino-5-(2-methylpropyl)oxolan-2-one
• CAS: 204511-95-5
• 化学式: C₁₈H₃₂N₂O₃
• 分子量: 324.464
• InChiKey: WCKTWOADVCHLEG-LMDAOGCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  51.13
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3E,5R)-3-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]imino-5-(2-methylpropyl)oxolan-2-one 在 palladium on activated charcoal 吡啶 、 氢气 、 臭氧 作用下， 以 乙醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 (3S,5R)-(+)-3-acetoxy-5-(2-methylpropyl)-tetrahydrofuran-2-one
  参考文献：
  名称：

  Diastereo- and enantioselective synthesis of 4- and 3,4-substituted 2-acetoxy-butyrolactones

  摘要：

  An efficient asymmetric synthesis of 4-mono- and 3,4-disubstituted 2-acetoxy-butyrolactones 2 has been developed, based on a hydrazone-mediated asymmetric aldol reaction, an intramolecular lactonization and a stereoselective hydrogenation of the resulting butenolides 1. An application of this process in the synthesis of the natural hunger substance 3 (ee = 90%) is also presented, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00283-5
• 作为产物：
  描述：

  (S)-1-氨基-2-(二乙基甲氧基甲基)吡咯烷 在 potassium tert-butylate 、 对甲苯磺酸 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， 反应 1.0h， 生成 (3E,5R)-3-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]imino-5-(2-methylpropyl)oxolan-2-one
  参考文献：
  名称：

  Diastereo- and enantioselective synthesis of 4- and 3,4-substituted 2-acetoxy-butyrolactones

  摘要：

  An efficient asymmetric synthesis of 4-mono- and 3,4-disubstituted 2-acetoxy-butyrolactones 2 has been developed, based on a hydrazone-mediated asymmetric aldol reaction, an intramolecular lactonization and a stereoselective hydrogenation of the resulting butenolides 1. An application of this process in the synthesis of the natural hunger substance 3 (ee = 90%) is also presented, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00283-5

文献信息

• Enders, Dieter; Dyker, Hubert; Leusink, Frederik R., Chemistry - A European Journal, 1998, vol. 4, # 2, p. 311 - 320
  作者：Enders, Dieter、Dyker, Hubert、Leusink, Frederik R.

  DOI：——

  日期：——
• Diastereo- and enantioselective synthesis of 4- and 3,4-substituted 2-acetoxy-butyrolactones
  作者：Dieter Enders、Hongbin Sun、Frederik R. Leusink

  DOI：10.1016/s0040-4020(99)00283-5

  日期：1999.5

  An efficient asymmetric synthesis of 4-mono- and 3,4-disubstituted 2-acetoxy-butyrolactones 2 has been developed, based on a hydrazone-mediated asymmetric aldol reaction, an intramolecular lactonization and a stereoselective hydrogenation of the resulting butenolides 1. An application of this process in the synthesis of the natural hunger substance 3 (ee = 90%) is also presented, (C) 1999 Elsevier Science Ltd. All rights reserved.