Methyl 6,7-benzo-4-phenyl-8-oxatricyclo<3.2.1.0^2,4>oct-6-ene-2-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: Methyl 6,7-benzo-4-phenyl-8-oxatricyclo<3.2.1.0^2,4>oct-6-ene-2-carboxylate
• 英文别名: Methyl 6,7-benzo-4-phenyl-8-oxatricyclo[3.2.1.0^2,4]oct-6-ene-2-carboxylate；Methyl 1,8,11-triphenyl-12-oxatetracyclo[6.3.1.02,7.09,11]dodeca-2,4,6-triene-9-carboxylate
• 化学式: C₃₁H₂₄O₃
• 分子量: 444.53
• InChiKey: ADXRMOUZWJVUMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-3-苯基-3-甲基丙烯酸甲酯 在 dirhodium tetraacetate 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酰叠氮 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 Methyl 6,7-benzo-4-phenyl-8-oxatricyclo<3.2.1.0^2,4>oct-6-ene-2-carboxylate
  参考文献：
  名称：

  Carbenoid versus Vinylogous Reactivity in Rhodium(II)-Stabilized Vinylcarbenoids

  摘要：

  Rhodium(II)-stabilized vinylcarbenoid intermediates display electrophilic character at both the carbenoid site and the vinylogous position. The solvent and catalyst as well as the vinylcarbenoid structure have major effects on the regiochemical outcome of the reaction of vinylcarbenoids with alkenes and dienes. Reaction of vinylcarbenoids with vinyl ethers can lead to the formation of either cyclopropanes or cyclopentenes while reaction of vinylcarbenoids with cyclopentadiene can lead to the formation of either bicyclo[3.2.1]octadiene or bicyclo[2.2.1]heptene derivatives.

  DOI：

  10.1021/jo00095a031

文献信息

• Davies Huw M. L., Hu Baihua, Saikali Elie, Bruzinski Paul R., J. Org. Chem, 59 (1994) N 16, S 4535-4541
  作者：Davies Huw M. L., Hu Baihua, Saikali Elie, Bruzinski Paul R.

  DOI：——

  日期：——
• Carbenoid versus Vinylogous Reactivity in Rhodium(II)-Stabilized Vinylcarbenoids
  作者：Huw M. L. Davies、Baihua Hu、Elie Saikali、Paul R. Bruzinski

  DOI：10.1021/jo00095a031

  日期：1994.8

  Rhodium(II)-stabilized vinylcarbenoid intermediates display electrophilic character at both the carbenoid site and the vinylogous position. The solvent and catalyst as well as the vinylcarbenoid structure have major effects on the regiochemical outcome of the reaction of vinylcarbenoids with alkenes and dienes. Reaction of vinylcarbenoids with vinyl ethers can lead to the formation of either cyclopropanes or cyclopentenes while reaction of vinylcarbenoids with cyclopentadiene can lead to the formation of either bicyclo[3.2.1]octadiene or bicyclo[2.2.1]heptene derivatives.