(2S,3S,4S)-2-allyl-3-hydroxy-4-methyl-4-butanolide | 861902-86-5

• 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: (2S,3S,4S)-2-allyl-3-hydroxy-4-methyl-4-butanolide
• 英文别名: (3R,4S,5S)-4-hydroxy-5-methyl-3-prop-2-enyloxolan-2-one
• CAS: 861902-86-5
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: VNXDDDITQDJISD-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-allyl-3-hydroxy-4-methyl-4-butanolide 在 Wilkinson's catalyst 、 Grubbs catalyst first generation 、 氢气 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 15.5h， 生成 (3R,4S,5R)-3-dihydro-4,5-dihydroxy-3-tetradecylfuran-2(3H)-one
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol

  摘要：

  A novel approach to natural beta-hydroxy-gamma-lactone 2 from 2,5-anhydro-D-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathes is of 3-allyl-4-hydroxy-gamma-lactone 16 with 1-tridecene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.059
• 作为产物：
  描述：

  (2S,3aR,6S,6aS)-2-hydroxymethyl-6-methyltetrahydrofuro[3,4-b]furan-4-one 在 4-二甲氨基吡啶 、 水 、 三乙胺 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 25.0h， 生成 (2S,3S,4S)-2-allyl-3-hydroxy-4-methyl-4-butanolide
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol

  摘要：

  A novel approach to natural beta-hydroxy-gamma-lactone 2 from 2,5-anhydro-D-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathes is of 3-allyl-4-hydroxy-gamma-lactone 16 with 1-tridecene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.059

文献信息

• Stereoselective synthesis of (2R,3S,4S)-3-hydroxy-4-methyl-2-tetradecyl-4-butanolide starting from 2,5-anhydro-d-mannitol
  作者：Shunya Takahashi、Narihito Ogawa、Nobuo Sakairi、Tadashi Nakata

  DOI：10.1016/j.tet.2005.04.059

  日期：2005.7

  A novel approach to natural beta-hydroxy-gamma-lactone 2 from 2,5-anhydro-D-mannitol (1) is described. The key reactions in this synthesis include stereoselective methylation of aldehyde 3 with lithium dimethylcuprate, an intramolecular radical cyclization of seleno carbonate 11 and an intermolecular cross-metathes is of 3-allyl-4-hydroxy-gamma-lactone 16 with 1-tridecene. (c) 2005 Elsevier Ltd. All rights reserved.