ethyl 3'-chloro-10'-oxo-10'H-spiro[cyclohexane-1,9'-phenanthrene]-7'-carboxylate | 1233011-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: ethyl 3'-chloro-10'-oxo-10'H-spiro[cyclohexane-1,9'-phenanthrene]-7'-carboxylate
• 英文别名: Ethyl 6'-chloro-9'-oxospiro[cyclohexane-1,10'-phenanthrene]-2'-carboxylate；ethyl 6'-chloro-9'-oxospiro[cyclohexane-1,10'-phenanthrene]-2'-carboxylate
• CAS: 1233011-89-6
• 化学式: C₂₂H₂₁ClO₃
• 分子量: 368.86
• InChiKey: ILXQBBYHHDHUKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-氯苯基)(环己基)甲酮 、 对碘苯甲酸乙酯 在 palladium diacetate 、 三氟乙酸 、 silver(l) oxide 作用下， 反应 20.0h， 以61%的产率得到ethyl 3'-chloro-10'-oxo-10'H-spiro[cyclohexane-1,9'-phenanthrene]-7'-carboxylate
  参考文献：
  名称：

  Synthesis of Phenanthrone Derivatives from sec-Alkyl Aryl Ketones and Aryl Halides via a Palladium-Catalyzed Dual C−H Bond Activation and Enolate Cyclization

  摘要：

  A palladium-catalyzed chelation-assisted C-H activation of alkyl aryl ketones and their reaction with aryl iodides to afford ortho-arylated products is described. For sec-alkyl aryl ketones, the catalytic reaction proceeds further to give 10,10-dialkylphenanthrone derivatives. A possible reaction mechanism involving directed dual C-H bond activation and enolate cyclization for the formation of 10,10-dialkylphenanthrone derivatives is proposed.

  DOI：

  10.1021/ja1026248

文献信息

• Synthesis of Phenanthrone Derivatives from <i>sec-</i>Alkyl Aryl Ketones and Aryl Halides via a Palladium-Catalyzed Dual C−H Bond Activation and Enolate Cyclization
  作者：Parthasarathy Gandeepan、Kanniyappan Parthasarathy、Chien-Hong Cheng

  DOI：10.1021/ja1026248

  日期：2010.6.30

  A palladium-catalyzed chelation-assisted C-H activation of alkyl aryl ketones and their reaction with aryl iodides to afford ortho-arylated products is described. For sec-alkyl aryl ketones, the catalytic reaction proceeds further to give 10,10-dialkylphenanthrone derivatives. A possible reaction mechanism involving directed dual C-H bond activation and enolate cyclization for the formation of 10,10-dialkylphenanthrone derivatives is proposed.