(2E)-2-diazonio-1-methoxy-1-oxo-4,4-diphenylhepta-2,6-dien-3-olate | 564450-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E)-2-diazonio-1-methoxy-1-oxo-4,4-diphenylhepta-2,6-dien-3-olate
• CAS: 564450-52-8
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: QQRVPXHRPWFIMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-2-diazonio-1-methoxy-1-oxo-4,4-diphenylhepta-2,6-dien-3-olate 在 dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate] bis(ethyl acetate) 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 9.5h， 生成
  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：

  2,2-二苯基戊-4-烯酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 、 甲烷磺酰基叠氮化物 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 生成 (2E)-2-diazonio-1-methoxy-1-oxo-4,4-diphenylhepta-2,6-dien-3-olate
  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

文献信息

• Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate]: an exceptionally effective Rh(II) catalyst for enantiotopically selective aromatic C–H insertions of diazo ketoesters
  作者：Hideyuki Tsutsui、Yukiko Yamaguchi、Shinji Kitagaki、Seiichi Nakamura、Masahiro Anada、Shunichi Hashimoto

  DOI：10.1016/s0957-4166(03)00075-2

  日期：2003.4

  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.