O-2-(2-phenyl-1(Z)-propenyl)-2-(2(E)-butenyl)-4(Z)-hexenyl S-methyl dithiocarbonate | 133129-84-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-2-(2-phenyl-1(Z)-propenyl)-2-(2(E)-butenyl)-4(Z)-hexenyl S-methyl dithiocarbonate
• 英文别名: O-[(E)-2-[(E)-but-2-enyl]-2-[(Z)-2-phenylprop-1-enyl]hex-4-enyl] methylsulfanylmethanethioate
• CAS: 133129-84-7
• 化学式: C₂₁H₂₈OS₂
• 分子量: 360.585
• InChiKey: RZPJZEFNSDKOOY-ACRKOEARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  O-2-(2-phenyl-1(Z)-propenyl)-2-(2(E)-butenyl)-4(Z)-hexenyl 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 5-(2(E)-butenyl)-7-ethyl-8-methyl-8-phenyl-3-oxabicyclo<3.3.0>octane-2-thione 、 5-(2(E)-butenyl)-7-ethyl-8-methyl-8-phenyl-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：

  在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 4.08h， 生成 O-2-(2-phenyl-1(Z)-propenyl)-2-(2(E)-butenyl)-4(Z)-hexenyl 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