6-Ethenyl-1,1a,6,10b-tetrahydrodibenzocyclopropacyclohepten-6-ol | 169687-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 6-Ethenyl-1,1a,6,10b-tetrahydrodibenzocyclopropacyclohepten-6-ol
• 英文别名: 6-Ethenyl-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-ol；11-Ethenyltetracyclo[10.4.0.02,4.05,10]hexadeca-1(16),5,7,9,12,14-hexaen-11-ol
• CAS: 169687-58-5
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: BILWCTBKYVOJDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-Ethenyl-1,1a,6,10b-tetrahydrodibenzocyclopropacyclohepten-6-ol 在 sodium tetrahydroborate 、 碘 、 silver(I) acetate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 42.0h， 生成 7-<(4-Methyl-1-piperazinyl)methyl>-1a,6,7,11b-tetrahydrodibenzocyclopropacycloocten-6-ol
  参考文献：
  名称：

  .beta.-Iodo Ketones by Prevost Reaction Of Vinyl Carbinols

  摘要：

  Treatment of alpha-ethenyl-alpha-phenylbenzenemethanol with iodine and silver acetate in either acetic acid or benzene gave 1,2-diphenyl-3-iodo-1-propanone (6) in 85% yield. Ring enlargements involving similar rearrangements were observed with a number of cyclic vinyl carbinols. In some cases, mixtures of normal Prevost products and rearranged beta-iodo ketones were obtained. The exact scope of this apparently novel reaction remains to be elucidated. Treatment of the beta-iodo ketones with DBU gave the corresponding alpha,beta-unsaturated ketones from which a number of amino ketones and amino alcohols were prepared by conjugate addition followed by reduction.

  DOI：

  10.1021/jo00119a021
• 作为产物：
  描述：

  乙烯基溴化镁 、 1,1a,6,10b-Tetrahydrodibenzocyclopropacyclohepten-6-one 以87%的产率得到6-Ethenyl-1,1a,6,10b-tetrahydrodibenzocyclopropacyclohepten-6-ol
  参考文献：
  名称：

  .beta.-Iodo Ketones by Prevost Reaction Of Vinyl Carbinols

  摘要：

  Treatment of alpha-ethenyl-alpha-phenylbenzenemethanol with iodine and silver acetate in either acetic acid or benzene gave 1,2-diphenyl-3-iodo-1-propanone (6) in 85% yield. Ring enlargements involving similar rearrangements were observed with a number of cyclic vinyl carbinols. In some cases, mixtures of normal Prevost products and rearranged beta-iodo ketones were obtained. The exact scope of this apparently novel reaction remains to be elucidated. Treatment of the beta-iodo ketones with DBU gave the corresponding alpha,beta-unsaturated ketones from which a number of amino ketones and amino alcohols were prepared by conjugate addition followed by reduction.

  DOI：

  10.1021/jo00119a021

文献信息

• .beta.-Iodo Ketones by Prevost Reaction Of Vinyl Carbinols
  作者：Engelbert Ciganek、J. C. Calabrese

  DOI：10.1021/jo00119a021

  日期：1995.7

  Treatment of alpha-ethenyl-alpha-phenylbenzenemethanol with iodine and silver acetate in either acetic acid or benzene gave 1,2-diphenyl-3-iodo-1-propanone (6) in 85% yield. Ring enlargements involving similar rearrangements were observed with a number of cyclic vinyl carbinols. In some cases, mixtures of normal Prevost products and rearranged beta-iodo ketones were obtained. The exact scope of this apparently novel reaction remains to be elucidated. Treatment of the beta-iodo ketones with DBU gave the corresponding alpha,beta-unsaturated ketones from which a number of amino ketones and amino alcohols were prepared by conjugate addition followed by reduction.