O-2-ethenyl-2-(2-propenyl)-4-pentenyl S-methyl dithiocarbonate | 133129-79-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: O-2-ethenyl-2-(2-propenyl)-4-pentenyl S-methyl dithiocarbonate
• 英文别名: O-(2-ethenyl-2-prop-2-enylpent-4-enyl) methylsulfanylmethanethioate
• CAS: 133129-79-0
• 化学式: C₁₂H₁₈OS₂
• 分子量: 242.406
• InChiKey: VUNBBXCDMXDKON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-2-ethenyl-2-(2-propenyl)-4-pentenyl S-methyl dithiocarbonate 在 偶氮二异丁腈 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 7-methyl-5-(2-propenyl)-3-oxabicyclo<3.3.0>octane-2-thione 、 7-methyl-5-(2-propenyl)-3-oxabicyclo<3.3.0>octane-2-thione
  参考文献：
  名称：

  Tandem radical cyclization of acyclic homoallylic xanthates: cyclopentannulated .gamma.-thionolactone and .gamma.-lactones

  摘要：

  The first tandem radical cyclization of linear homoallylic xanthates was explored. Homoallylic xanthates prepared from alpha,beta-unsaturated esters were easily cyclized by tin hydride with an radical initiator to give the corresponding thionolactone annulated cyclopentane skeleton in a high yield. The stereochemistry of cyclized products was also discussed. Thionolactones obtained were oxidized chemoselectivity with m-CPBA under neutral condition to afford gamma-lactones in a high yield.

  DOI：

  10.1021/jo00008a048
• 作为产物：
  描述：

  2-烯丙基-2-乙烯基-4-烯酸乙酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 O-2-ethenyl-2-(2-propenyl)-4-pentenyl S-methyl dithiocarbonate
  参考文献：
  名称：

  Tandem radical cyclization of acyclic homoallylic xanthates: cyclopentannulated .gamma.-thionolactone and .gamma.-lactones

  摘要：

  The first tandem radical cyclization of linear homoallylic xanthates was explored. Homoallylic xanthates prepared from alpha,beta-unsaturated esters were easily cyclized by tin hydride with an radical initiator to give the corresponding thionolactone annulated cyclopentane skeleton in a high yield. The stereochemistry of cyclized products was also discussed. Thionolactones obtained were oxidized chemoselectivity with m-CPBA under neutral condition to afford gamma-lactones in a high yield.

  DOI：

  10.1021/jo00008a048

文献信息

• Tandem radical cyclization of acyclic homoallylic xanthates: cyclopentannulated .gamma.-thionolactone and .gamma.-lactones
  作者：Seiji Iwasa、Makoto Yamamoto、Shigeo Kohmoto、Kazutoshi Yamada

  DOI：10.1021/jo00008a048

  日期：1991.4

  The first tandem radical cyclization of linear homoallylic xanthates was explored. Homoallylic xanthates prepared from alpha,beta-unsaturated esters were easily cyclized by tin hydride with an radical initiator to give the corresponding thionolactone annulated cyclopentane skeleton in a high yield. The stereochemistry of cyclized products was also discussed. Thionolactones obtained were oxidized chemoselectivity with m-CPBA under neutral condition to afford gamma-lactones in a high yield.