Methyl β-tert-butyl-2-nitrohippurate | 171819-62-8

• 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: Methyl β-tert-butyl-2-nitrohippurate
• 英文别名: Methyl 2-[tert-butyl-(2-nitrobenzoyl)amino]acetate
• CAS: 171819-62-8
• 化学式: C₁₄H₁₈N₂O₅
• 分子量: 294.307
• InChiKey: LJARABYNDYBPQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl β-tert-butyl-2-nitrohippurate 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 、 copper(l) iodide 硫酸 、 氢气 、 碘 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 20.34h， 生成 4-tert-butyl-3,4-dihydro-7-[(trimethylsilyl)ethynyl]-1H-1,4-benzodiazepine-2,5-dione
  参考文献：
  名称：

  Palladium(II)-mediated coupling reactions of bromo- and iodo-1H-1,4-benzodiazepine-2,5-diones. A route to functionalized benzodiazepinediones

  摘要：

  A series of 7-, 8-, and 9-bromo- and iodo-1,4-benzodiazepine-2,5-diones have been prepared and examined as substrates for palladium(II)-mediated coupling reactions with alkenes, alkynes, arylstannanes, and heteroarylstannanes. The benzodiazepinediones 6a,e,g were prepared from the reaction of o-nitrobenzoyl chlorides 3a-c and methyl tert-butylglycinate followed by nitro reduction and cyclization. Regioselective halogenation gave 6c,d,f. Bromo- and iodobenzodiazepinediones 6c,d,f,g were then converted to alkenyl-, alkynyl-, aryl-, and heteroaryl-substituted benzodiazepinediones in moderate to good yield in the presence of palladium(II).

  DOI：

  10.1021/jo00123a016
• 作为产物：
  描述：

  N-(t-butyl)glycine methyl ester 、 2-硝基苯甲酰氯 在 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 以60%的产率得到Methyl β-tert-butyl-2-nitrohippurate
  参考文献：
  名称：

  Palladium(II)-mediated coupling reactions of bromo- and iodo-1H-1,4-benzodiazepine-2,5-diones. A route to functionalized benzodiazepinediones

  摘要：

  A series of 7-, 8-, and 9-bromo- and iodo-1,4-benzodiazepine-2,5-diones have been prepared and examined as substrates for palladium(II)-mediated coupling reactions with alkenes, alkynes, arylstannanes, and heteroarylstannanes. The benzodiazepinediones 6a,e,g were prepared from the reaction of o-nitrobenzoyl chlorides 3a-c and methyl tert-butylglycinate followed by nitro reduction and cyclization. Regioselective halogenation gave 6c,d,f. Bromo- and iodobenzodiazepinediones 6c,d,f,g were then converted to alkenyl-, alkynyl-, aryl-, and heteroaryl-substituted benzodiazepinediones in moderate to good yield in the presence of palladium(II).

  DOI：

  10.1021/jo00123a016

文献信息

• Palladium(II)-mediated coupling reactions of bromo- and iodo-1H-1,4-benzodiazepine-2,5-diones. A route to functionalized benzodiazepinediones
  作者：Gary M. Karp

  DOI：10.1021/jo00123a016

  日期：1995.9

  A series of 7-, 8-, and 9-bromo- and iodo-1,4-benzodiazepine-2,5-diones have been prepared and examined as substrates for palladium(II)-mediated coupling reactions with alkenes, alkynes, arylstannanes, and heteroarylstannanes. The benzodiazepinediones 6a,e,g were prepared from the reaction of o-nitrobenzoyl chlorides 3a-c and methyl tert-butylglycinate followed by nitro reduction and cyclization. Regioselective halogenation gave 6c,d,f. Bromo- and iodobenzodiazepinediones 6c,d,f,g were then converted to alkenyl-, alkynyl-, aryl-, and heteroaryl-substituted benzodiazepinediones in moderate to good yield in the presence of palladium(II).