(S,S)-(+)-1-[3-Hydroxy-1-(2,6-di-tert-butyl-4-methoxy-1-phenoxycarbonyl)-3-phenyl-1-propylideneamino]-2-(1-ethyl-1-methoxypropyl)pyrrolidine | 148432-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (S,S)-(+)-1-[3-Hydroxy-1-(2,6-di-tert-butyl-4-methoxy-1-phenoxycarbonyl)-3-phenyl-1-propylideneamino]-2-(1-ethyl-1-methoxypropyl)pyrrolidine
• 英文别名: (2,6-ditert-butyl-4-methoxyphenyl) (2E,4S)-4-hydroxy-2-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]imino-4-phenylbutanoate
• CAS: 148432-25-1
• 化学式: C₃₅H₅₂N₂O₅
• 分子量: 580.808
• InChiKey: XADFYUYQQCLEHE-VNURBOKCSA-N

物化性质

• 沸点：
  647.4±65.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S,S)-(+)-1-[3-Hydroxy-1-(2,6-di-tert-butyl-4-methoxy-1-phenoxycarbonyl)-3-phenyl-1-propylideneamino]-2-(1-ethyl-1-methoxypropyl)pyrrolidine 在 吡啶 、 potassium tert-butylate 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-(-)-3-acetoxy-5-phenyl-2(5H)-furanone
  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 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 (S,S)-(+)-1-[3-Hydroxy-1-(2,6-di-tert-butyl-4-methoxy-1-phenoxycarbonyl)-3-phenyl-1-propylideneamino]-2-(1-ethyl-1-methoxypropyl)pyrrolidine
  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：——
• Enders, Dieter; Dyker, Hubert; Raabe, Gerhard, Angewandte Chemie, 1993, vol. 105, # 3, p. 420 - 423
  作者：Enders, Dieter、Dyker, Hubert、Raabe, Gerhard

  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.