cis-2,3-diphenyl-1-benzoyl(meta carboxylic acid)cyclopropane | 845727-31-3

• 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: cis-2,3-diphenyl-1-benzoyl(meta carboxylic acid)cyclopropane
• CAS: 845727-31-3
• 化学式: C₂₃H₁₈O₃
• 分子量: 342.394
• InChiKey: UXVWADLFYVVEOA-AERCQKQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-2,3-diphenyl-1-benzoyl(meta carboxylic acid)cyclopropane 、 S-(-)-2-甲基-1-丁醇 在 4-二甲氨基吡啶 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Enhanced Diastereoselectivity via Confinement:  Diastereoselective Photoisomerization of 2,3-Diphenyl-1-benzoylcyclopropane Derivatives within Zeolites

  摘要：

  Photochemistry of optically pure trans-2,3-diphenyl-1-benzoylcyclopropane has been examined in isotropic solution and within zeolites. Results suggest that it isomerizes by cleavage of either the C-1-C-2 or C-1-C-3 bond. From the perspective of chiral induction, photoisomerization of cis-2,3-diphenyl-1-benzoylcyclopropane derivatives with chiral auxiliaries placed at the meta and para positions of the benzoyl group have been examined both in isotropic solution and within zeolites. Whereas in isotropic solution the chiral auxiliaries placed at the meta position exhibit very little influence during the conversion of triplet cis-2,3-diphenyl-1-benzoylcyclopropane derivatives, they have significant influence within zeolites. For example, a-methyl benzylamine placed at the meta position of the benzoyl group (via an amide bond) yields the trans isomer with a diastereoselectivity (de) of 71% within NaY zeolite, whereas in solution no de is obtained. The chiral induction process within zeolites depends on the nature of the alkali ion and on the presence of water. Results suggest that the chiral auxiliary is able to control the bond being cleaved (C-1-C-2 VS. C-1-C-3 bond) within a zeolite, but it is unable to do so in an isotropic solution.

  DOI：

  10.1021/jo049697n
• 作为产物：
  描述：

  (1α,2β,3β)-2,3-diphenylcyclopropanecarboxylic acid 在 异丙基氯化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 cis-2,3-diphenyl-1-benzoyl(meta carboxylic acid)cyclopropane
  参考文献：
  名称：

  Enhanced Diastereoselectivity via Confinement:  Diastereoselective Photoisomerization of 2,3-Diphenyl-1-benzoylcyclopropane Derivatives within Zeolites

  摘要：

  Photochemistry of optically pure trans-2,3-diphenyl-1-benzoylcyclopropane has been examined in isotropic solution and within zeolites. Results suggest that it isomerizes by cleavage of either the C-1-C-2 or C-1-C-3 bond. From the perspective of chiral induction, photoisomerization of cis-2,3-diphenyl-1-benzoylcyclopropane derivatives with chiral auxiliaries placed at the meta and para positions of the benzoyl group have been examined both in isotropic solution and within zeolites. Whereas in isotropic solution the chiral auxiliaries placed at the meta position exhibit very little influence during the conversion of triplet cis-2,3-diphenyl-1-benzoylcyclopropane derivatives, they have significant influence within zeolites. For example, a-methyl benzylamine placed at the meta position of the benzoyl group (via an amide bond) yields the trans isomer with a diastereoselectivity (de) of 71% within NaY zeolite, whereas in solution no de is obtained. The chiral induction process within zeolites depends on the nature of the alkali ion and on the presence of water. Results suggest that the chiral auxiliary is able to control the bond being cleaved (C-1-C-2 VS. C-1-C-3 bond) within a zeolite, but it is unable to do so in an isotropic solution.

  DOI：

  10.1021/jo049697n