2-(o-ethynylphenyl)-1-(3-hydroxypropyl)-6,6-dimethyl-4,8-dioxaspiro[2.5]oct-1-ene | 1093862-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(o-ethynylphenyl)-1-(3-hydroxypropyl)-6,6-dimethyl-4,8-dioxaspiro[2.5]oct-1-ene
• 英文别名: 3-[2-(2-Ethynylphenyl)-6,6-dimethyl-4,8-dioxaspiro[2.5]oct-1-en-1-yl]propan-1-ol
• CAS: 1093862-73-7
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: NADUGQMYWYTUPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(o-ethynylphenyl)-1-(3-hydroxypropyl)-6,6-dimethyl-4,8-dioxaspiro[2.5]oct-1-ene 在 吗啉 、 碘 作用下， 以 苯 为溶剂， 反应 0.5h， 以78%的产率得到1-(3-hydroxypropyl)-2-(o-(iodoethynyl)phenyl)-6,6-dimethyl-4,8-dioxaspiro[2.5]oct-1-ene
  参考文献：
  名称：

  Photochemical Generation and Reversible Cycloaromatization of a Nine-Membered Ring Cyclic Enediyne

  摘要：

  Irradiation of the nine-membered ring enediyne precursor, which has one of its triple bonds masked as cyclopropenone, efficiently (Phi = 0.34) generates the reactive 4,5-benzocyclonona-2,6-diynol. The latter rapidly equilibrates with the corresponding 1,4-didehydronaphthalene diradical and then undergoes rate-limiting hydrogen abstraction to produce the ultimate product of the Bergman cyclization, benz[f]indanol.

  DOI：

  10.1021/ja8077076
• 作为产物：
  描述：

  1-(3-acetoxypropyl)-2-(o-((trimethylsilyl)ethynyl)phenyl)-6,6-dimethyl-4,8-dioxaspiro[2.5]oct-1-ene 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到2-(o-ethynylphenyl)-1-(3-hydroxypropyl)-6,6-dimethyl-4,8-dioxaspiro[2.5]oct-1-ene
  参考文献：
  名称：

  Photochemical Generation and Reversible Cycloaromatization of a Nine-Membered Ring Cyclic Enediyne

  摘要：

  Irradiation of the nine-membered ring enediyne precursor, which has one of its triple bonds masked as cyclopropenone, efficiently (Phi = 0.34) generates the reactive 4,5-benzocyclonona-2,6-diynol. The latter rapidly equilibrates with the corresponding 1,4-didehydronaphthalene diradical and then undergoes rate-limiting hydrogen abstraction to produce the ultimate product of the Bergman cyclization, benz[f]indanol.

  DOI：

  10.1021/ja8077076