(3R,4S,5S)-3-butyl-4-(methoxymethoxy)-5-methyloxolan-2-one | 342386-04-3

• 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: (3R,4S,5S)-3-butyl-4-(methoxymethoxy)-5-methyloxolan-2-one
• CAS: 342386-04-3
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: QWCXTUDSVXNIFO-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-3-butyl-4-(methoxymethoxy)-5-methyloxolan-2-one 在 盐酸 作用下， 以 甲醇 为溶剂， 以88%的产率得到(3R,4S,5S)-3-butyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Asymmetric synthesis of (−)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction

  摘要：

  Enantiocontrolled syntheses of the natural lactones 1 and 2 were achieved based on a tungsten-mediated cyclization. The whole syntheses comprise of six or seven steps from readily available 1-trimethylsilyl-pent-1-yne; the overall yields are 25 and 28% for 1 and 2, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00189-7
• 作为产物：
  描述：

  (E)-trimethyl(pent-3-en-1-yn-1-yl)silane 在 palladium on activated charcoal AD-mix-α 、 copper(l) iodide 、 cyclopentadienylW(carbonyl)3 、 甲基磺酰胺 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二乙胺 为溶剂， 生成 (3R,4S,5S)-3-butyl-4-(methoxymethoxy)-5-methyloxolan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of (−)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction

  摘要：

  Enantiocontrolled syntheses of the natural lactones 1 and 2 were achieved based on a tungsten-mediated cyclization. The whole syntheses comprise of six or seven steps from readily available 1-trimethylsilyl-pent-1-yne; the overall yields are 25 and 28% for 1 and 2, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00189-7

文献信息

• Asymmetric synthesis of (−)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction
  作者：Bo Liu、Ming-Jung Chen、Ching-Yu Lo、Rai-Shung Liu

  DOI：10.1016/s0040-4039(01)00189-7

  日期：2001.3

  Enantiocontrolled syntheses of the natural lactones 1 and 2 were achieved based on a tungsten-mediated cyclization. The whole syntheses comprise of six or seven steps from readily available 1-trimethylsilyl-pent-1-yne; the overall yields are 25 and 28% for 1 and 2, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.