2-Prop-2-ynyl-2-vinyl-pent-4-ynoic acid ethyl ester | 42998-22-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Prop-2-ynyl-2-vinyl-pent-4-ynoic acid ethyl ester
• CAS: 42998-22-1
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: IVGVZKFHZTZFOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-Prop-2-ynyl-2-vinyl-pent-4-ynoic acid ethyl ester 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-propynyl)-4-pentynyl 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
• 作为产物：
  描述：

  反式-2-丁烯酸乙酯 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 反应 1.17h， 生成 2-Prop-2-ynyl-2-vinyl-pent-4-ynoic acid ethyl ester
  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