(R)-(-)-3-acetoxy-5-butyl-2(5H)-furanone | 235765-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (R)-(-)-3-acetoxy-5-butyl-2(5H)-furanone
• 英文别名: [(2R)-2-butyl-5-oxo-2H-furan-4-yl] acetate
• CAS: 235765-43-2
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: SXCLDHOMFHBAQE-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-acetoxy-5-butyl-2(5H)-furanone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (3S,5R)-(+)-3-acetoxy-5-butyl-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：

  (3E,5R)-5-butyl-3-[(2S)-2-(3-methoxypentan-3-yl)pyrrolidin-1-yl]iminooxolan-2-one 在 吡啶 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (R)-(-)-3-acetoxy-5-butyl-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

文献信息

• 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.