methyl 2-benzoyl-1,4-dihydro-1,4-ethenonaphthalene-3-carboxylate | 135107-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 2-benzoyl-1,4-dihydro-1,4-ethenonaphthalene-3-carboxylate
• CAS: 135107-66-3
• 化学式: C₂₁H₁₆O₃
• 分子量: 316.356
• InChiKey: ODADEHCDKSAQEC-UHFFFAOYSA-N

物化性质

• 沸点：
  472.2±45.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 2-benzoyl-1,4-dihydro-1,4-ethenonaphthalene-3-carboxylate 以 氘代氯仿 为溶剂， 生成 6c-Benzoyl-6b,6c-dihydro-2aH-benzo[a]cyclopropa[cd]pentalene-2b-carboxylic acid methyl ester
  参考文献：
  名称：

  Selective solid-state photorearrangement through the less stable of two possible biradical intermediates

  摘要：

  The photochemistry of methyl 2-benzoyl-1,4-dihydro-1,4-ethenonaphthalene-3-carboxylate is completely medium-dependent. In solution, two primary di-pi-methane-type photoproducts are formed. Neither of these products is produced when the photolysis is carried out in the solid state; instead, three new photoproducts are formed. The results are interpreted as being due to reaction through 1,3-biradical intermediates, the more stable of which are preferred in solution whereas the less stable ones are formed in the solid state as a result of topochemical restrictions of molecular motion. X-ray crystallographic evidence in support of these ideas is presented and discussed.

  DOI：

  10.1021/jo00031a030
• 作为产物：
  描述：

  1,4-dihydro-1,4-ethenonaphthalene-2,3-dicarboxylic acid monomethyl ester 在 三氯化铝 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.75h， 生成 methyl 2-benzoyl-1,4-dihydro-1,4-ethenonaphthalene-3-carboxylate
  参考文献：
  名称：

  Selective solid-state photorearrangement through the less stable of two possible biradical intermediates

  摘要：

  The photochemistry of methyl 2-benzoyl-1,4-dihydro-1,4-ethenonaphthalene-3-carboxylate is completely medium-dependent. In solution, two primary di-pi-methane-type photoproducts are formed. Neither of these products is produced when the photolysis is carried out in the solid state; instead, three new photoproducts are formed. The results are interpreted as being due to reaction through 1,3-biradical intermediates, the more stable of which are preferred in solution whereas the less stable ones are formed in the solid state as a result of topochemical restrictions of molecular motion. X-ray crystallographic evidence in support of these ideas is presented and discussed.

  DOI：

  10.1021/jo00031a030