(3RS,4RS,7RS)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (3RS,4RS,7RS)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide
• 英文别名: (3aS,5S,7aS)-7a-methyl-5-prop-1-en-2-yl-3a,5,6,7-tetrahydro-3H-furo[3,2-b]pyran-2-one
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: AULQLQUPDNVFNJ-QXEWZRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(1,3-Dioxolan-2-yl)-2-methylpent-1-en-3-ol 在 N-甲基吗啉 、 盐酸 、 甲醇 、 samarium diiodide 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3RS,4RS,7RS)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide
  参考文献：
  名称：

  Synthesis of a lactone natural product found in Greek tobacco

  摘要：

  A short and stereoselective synthesis of (3R*,4R*,7R*)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide, a natural product isolated from cured tobacco leaves, has been completed in six steps and 22% overall yield. A samarium(II) iodide mediated reductive cyclisation has been used to construct the functionalised tetrahydropyranol core and subsequent sequential stereoselective addition of methyllithium and lactonisation furnished the natural product. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.039

文献信息

• Synthesis of a Greek tobacco lactonic natural product and its analogues
  作者：Andrea Zúñiga、Gonzalo Pazos、Pedro Besada、Yagamare Fall

  DOI：10.1016/j.tetlet.2012.05.151

  日期：2012.8

  A total synthesis of a Greek tobacco lactonic natural product and three of its analogues has been achieved using a commercially available starting material and our furan approach to oxacyclic systems, the proven scope of which is thus broadened. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of a lactone natural product found in Greek tobacco
  作者：J. Stephen Clark、Stewart T. Hayes、Alexander J. Blake、Luca Gobbi

  DOI：10.1016/j.tetlet.2007.02.039

  日期：2007.4

  A short and stereoselective synthesis of (3R*,4R*,7R*)-3,7-epoxy-4,8-dimethyl-8-nonen-4-olide, a natural product isolated from cured tobacco leaves, has been completed in six steps and 22% overall yield. A samarium(II) iodide mediated reductive cyclisation has been used to construct the functionalised tetrahydropyranol core and subsequent sequential stereoselective addition of methyllithium and lactonisation furnished the natural product. (c) 2007 Elsevier Ltd. All rights reserved.