(4S,5R,6S)-4-(1,3-dithiolan-2-yl)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-one | 1197132-98-1

• 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: (4S,5R,6S)-4-(1,3-dithiolan-2-yl)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-one
• 英文别名: (4S,5R,6S)-4-(1,3-dithiolan-2-yl)-5-hydroxy-6-methyloxan-2-one
• CAS: 1197132-98-1
• 化学式: C₉H₁₄O₃S₂
• 分子量: 234.34
• InChiKey: IRVZEPHOZYJQDQ-HAFWLYHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1R,3S,5S,6R)-ethyl 4-hydroxy-3-methyl-2-oxa-bicyclo[3.1.0]hexane-6-carboxylate 、 1,2-乙二硫醇 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(4S,5R,6S)-4-(1,3-dithiolan-2-yl)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Donor−Acceptor Substituted Cyclopropafuranones by Intramolecular Cyclopropanation of Vinylogous Carbonates: Divergent Synthesis of Tetrahydrofuran-3-one, Tetrahydropyran-3-one, and Lactones

  摘要：

  A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbonate with carbenes using copper catalyst is described. Each of the cyclopropane bonds of these two acceptor substituted cyclopropafuranones can be cleaved with complete regiocontrol by judicious choice of reaction conditions, leading to a diverse array of frameworks such as tetra hydrofuran-3-one, tetrahydropyran-3-one, and lactones.

  DOI：

  10.1021/ol902301h

文献信息

• Stereoselective Synthesis of Donor−Acceptor Substituted Cyclopropafuranones by Intramolecular Cyclopropanation of Vinylogous Carbonates: Divergent Synthesis of Tetrahydrofuran-3-one, Tetrahydropyran-3-one, and Lactones
  作者：Santosh J. Gharpure、Manoj K. Shukla、U. Vijayasree

  DOI：10.1021/ol902301h

  日期：2009.12.3

  A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbonate with carbenes using copper catalyst is described. Each of the cyclopropane bonds of these two acceptor substituted cyclopropafuranones can be cleaved with complete regiocontrol by judicious choice of reaction conditions, leading to a diverse array of frameworks such as tetra hydrofuran-3-one, tetrahydropyran-3-one, and lactones.