methyl 5-((tert-butyldimethylsilyloxy)(phenyl)amino)-2-diazo-3-oxo-5-phenylpentanoate | 1344025-66-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-((tert-butyldimethylsilyloxy)(phenyl)amino)-2-diazo-3-oxo-5-phenylpentanoate
• 英文别名: methyl 5-(N-[tert-butyl(dimethyl)silyl]oxyanilino)-2-diazo-3-oxo-5-phenylpentanoate
• CAS: 1344025-66-6
• 化学式: C₂₄H₃₁N₃O₄Si
• 分子量: 453.613
• InChiKey: MHWHAOMMUYPUGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-((tert-butyldimethylsilyloxy)(phenyl)amino)-2-diazo-3-oxo-5-phenylpentanoate 在 rhodium(II) acetate dimer 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到methyl (2S,5R)-2-[tert-butyl(dimethyl)silyl]oxy-3-oxo-1,5-diphenylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Multifunctionalized 3-Hydroxypyrroles in a Three-Step, One-Pot Cascade Process from Methyl 3-TBSO-2-diazo-3-butenoate and Nitrones

  摘要：

  The synthesis of N-aryl-2-carboxyl-3-hydroxy-5-arylpyrroles has been achieved in high yield by the combination of a TBSO-substituted vinyldiazoacetate and nitrones in a one-pot cascade process involving copper-catalyzed Mannich addition, dirhodium-catalyzed dinitrogen extrusion and N-OTBS insertion, and acid-promoted aromatization (elimination).

  DOI：

  10.1021/ol2026125
• 作为产物：
  描述：

  methyl 3-tert-butyldimethylsilyloxy-2-diazobut-3-enoate 、 N-(benzylidene)aniline N-oxide 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以94%的产率得到methyl 5-((tert-butyldimethylsilyloxy)(phenyl)amino)-2-diazo-3-oxo-5-phenylpentanoate
  参考文献：
  名称：

  Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with Nitrones

  摘要：

  Catalyst-controlled divergent addition reactions of enoldiazoacetamides with nitrones have been developed. By using copper(I) tetrafluoroborate/bisoxazoline complex as the catalyst, a [3+3]-cycloaddition reaction was achieved with excellent yield and enantioselectivity under exceptionally mild conditions, which represents the first highly enantioselective base-metal-catalyzed vinyl-carbene transformation. When the catalyst was changed to copper(I) triflate, Mannich addition products were formed in high yields with near exclusivity under otherwise identical conditions.

  DOI：

  10.1021/jacs.5b10860