(E)-5-Phenyl-2-((E)-3-phenyl-allyl)-2-vinyl-pent-4-en-1-ol | 133130-04-8

• 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: (E)-5-Phenyl-2-((E)-3-phenyl-allyl)-2-vinyl-pent-4-en-1-ol
• CAS: 133130-04-8
• 化学式: C₂₂H₂₄O
• 分子量: 304.432
• InChiKey: TXHTURZIJOSJBQ-KAVGSWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (E)-5-Phenyl-2-((E)-3-phenyl-allyl)-2-vinyl-pent-4-en-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-benzyl-5-(3-phenyl-2(E)-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：

  反式-2-丁烯酸乙酯 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 1.17h， 生成 (E)-5-Phenyl-2-((E)-3-phenyl-allyl)-2-vinyl-pent-4-en-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