neopentylglycol acetal of 6,7-didehydro-2,3,4,5-tetrahydro-5-hydroxy-1Hbenzo[a]cyclopropa[c]cyclononen-1-one | 1093862-76-0

• 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: neopentylglycol acetal of 6,7-didehydro-2,3,4,5-tetrahydro-5-hydroxy-1Hbenzo[a]cyclopropa[c]cyclononen-1-one
• 英文别名: 5,5-Dimethylspiro[1,3-dioxane-2,3'-tricyclo[8.4.0.02,4]tetradeca-1(14),2(4),10,12-tetraen-8-yne]-7'-ol
• CAS: 1093862-76-0
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: BILGJYXCMCNMOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• 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：

  neopentylglycol acetal of 6,7-didehydro-2,3,4,5-tetrahydro-5-hydroxy-1Hbenzo[a]cyclopropa[c]cyclononen-1-one 在 amberlyst resin 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以77%的产率得到6,7-didehydro-2,3,4,5-tetrahydro-5-hydroxy-1H-benzo[a]cyclopropa[c]cyclononen-1-one
  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：

  2-(o-(iodoethynyl)phenyl)-6,6-dimethyl1-(3-oxopropyl)-4,8-dioxaspiro[2.5]oct-1-ene 在 chromium dichloride 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以36%的产率得到neopentylglycol acetal of 6,7-didehydro-2,3,4,5-tetrahydro-5-hydroxy-1Hbenzo[a]cyclopropa[c]cyclononen-1-one
  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