2-ethenyl-2-prop-2-ynylpent-4-yn-1-ol | 133130-01-5

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 2-ethenyl-2-prop-2-ynylpent-4-yn-1-ol
• CAS: 133130-01-5
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: CJZYWMLMELAZIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-ethenyl-2-prop-2-ynylpent-4-yn-1-ol 在 偶氮二异丁腈 三正丁基氢锡 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成 7-methylene-5-(2-propynyl)-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-Vinyl-pent-4-ynoic acid ethyl ester 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 0.58h， 生成 2-ethenyl-2-prop-2-ynylpent-4-yn-1-ol
  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.