3-Methyl-2-oxo-3-phenyl-indan-1-carboxylic acid methyl ester | 164072-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 3-Methyl-2-oxo-3-phenyl-indan-1-carboxylic acid methyl ester
• 英文别名: methyl 3-methyl-2-oxo-3-phenyl-1H-indene-1-carboxylate
• CAS: 164072-88-2
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: KTDUPTNKZXMAQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  3-Methyl-2-oxo-3-phenyl-indan-1-carboxylic acid methyl ester 以 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 以97%的产率得到(S)-(-)-1-methyl-1-phenyl-2-indanone
  参考文献：
  名称：

  Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate]: an exceptionally effective Rh(II) catalyst for enantiotopically selective aromatic C–H insertions of diazo ketoesters

  摘要：

  Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh-2[(S)-TFPTTL](4), in which the phthalimido hydrogen atoms of the parent dirhodium(II) complex are substituted by fluorine atoms, dramatically enhances the reactivity and enantioselectivity (up to 97% ee) in intramolecular aromatic C-H insertion reactions of methyl 4-alkyl-2-diazo-4,4-diphenyl-3-oxopropionates. Catalysis with the use of 0.001 mol% of Rh-2[(S)-TFPTTL](4) has achieved the highest turnover number (up to 98,000 with the methyl substituent) ever recorded for chiral dirhodium(II) complex-catalyzed carbene transformations, without compromising the yield or enantioselectivity of the process. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00075-2
• 作为产物：
  描述：

  2,2-diphenylpropionyl chloride 在 dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate] bis(ethyl acetate) 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.33h， 生成 3-Methyl-2-oxo-3-phenyl-indan-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate]: an exceptionally effective Rh(II) catalyst for enantiotopically selective aromatic C–H insertions of diazo ketoesters

  摘要：

  Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh-2[(S)-TFPTTL](4), in which the phthalimido hydrogen atoms of the parent dirhodium(II) complex are substituted by fluorine atoms, dramatically enhances the reactivity and enantioselectivity (up to 97% ee) in intramolecular aromatic C-H insertion reactions of methyl 4-alkyl-2-diazo-4,4-diphenyl-3-oxopropionates. Catalysis with the use of 0.001 mol% of Rh-2[(S)-TFPTTL](4) has achieved the highest turnover number (up to 98,000 with the methyl substituent) ever recorded for chiral dirhodium(II) complex-catalyzed carbene transformations, without compromising the yield or enantioselectivity of the process. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00075-2