Dimethylethyl α-diazobicyclo<2.2.1>hept-5-ene-2-acetate | 156731-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Dimethylethyl α-diazobicyclo<2.2.1>hept-5-ene-2-acetate
• CAS: 156731-95-2
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: CMEGUWYOHBFEDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Dimethylethyl α-diazobicyclo<2.2.1>hept-5-ene-2-acetate 在 dirhodium tetraacetate 环戊二烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (Z)-5-(2-((Dimethylethoxy)carbonyl)ethylidene)bicyclo<2.2.1>hept-2-ene 、 (E)-5-(2-((Dimethylethoxy)carbonyl)ethylidene)bicyclo<2.2.1>hept-2-ene
  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
• 作为产物：
  描述：

  Dimethylethyl α-(N-(toluenesulfonyl)hydrazo)bicyclo<2.2.1>hept-5-ene-2-acetate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以36%的产率得到Dimethylethyl α-diazobicyclo<2.2.1>hept-5-ene-2-acetate
  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：——