2-(2-furyl)ethyl ethenesulfinate | 235104-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(2-furyl)ethyl ethenesulfinate
• 英文别名: 2-(Furan-2-yl)ethyl ethenesulfinate；2-(furan-2-yl)ethyl ethenesulfinate
• CAS: 235104-10-6
• 化学式: C₈H₁₀O₃S
• 分子量: 186.232
• InChiKey: TUHMXLBFUXWGKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-furyl)ethyl ethenesulfinate 在 氯化二乙基铝 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以53%的产率得到
  参考文献：
  名称：

  Highly Diastereoselective Intramolecular Diels−Alder Reactions of Furan-Tethered 1-Alkenesulfinic Acid Esters

  摘要：

  [GRAPHICS]The capture of selected 1-alkenesulfinyl chlorides with furan-tethered alcohols leads to the formation of diene-tethered 1-alkenesulfinate esters, The esters can spontaneously or with Lewis acid treatment undergo an IM DA reaction to form exo adducts with very high diastereoselectivity. Computational predictions using density functional theory indicate the preferred transition state for cyclization and find little preference for the sulfinyl configuration in the products.

  DOI：

  10.1021/ol990674i
• 作为产物：
  描述：

  β-2-呋喃基乙醇 、 ethenesulfinyl chloride 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以1.17 g的产率得到2-(2-furyl)ethyl ethenesulfinate
  参考文献：
  名称：

  Highly Diastereoselective Intramolecular Diels−Alder Reactions of Furan-Tethered 1-Alkenesulfinic Acid Esters

  摘要：

  [GRAPHICS]The capture of selected 1-alkenesulfinyl chlorides with furan-tethered alcohols leads to the formation of diene-tethered 1-alkenesulfinate esters, The esters can spontaneously or with Lewis acid treatment undergo an IM DA reaction to form exo adducts with very high diastereoselectivity. Computational predictions using density functional theory indicate the preferred transition state for cyclization and find little preference for the sulfinyl configuration in the products.

  DOI：

  10.1021/ol990674i

文献信息

• Highly Diastereoselective Intramolecular Diels−Alder Reactions of Furan-Tethered 1-Alkenesulfinic Acid Esters
  作者：Adrian L. Schwan、Jennifer L. Snelgrove、Mark L. Kalin、Robert D. J. Froese、Keiji Morokuma

  DOI：10.1021/ol990674i

  日期：1999.8.1

  [GRAPHICS]The capture of selected 1-alkenesulfinyl chlorides with furan-tethered alcohols leads to the formation of diene-tethered 1-alkenesulfinate esters, The esters can spontaneously or with Lewis acid treatment undergo an IM DA reaction to form exo adducts with very high diastereoselectivity. Computational predictions using density functional theory indicate the preferred transition state for cyclization and find little preference for the sulfinyl configuration in the products.