4-tert-Butyl-7-chloro-9-(2'-pyridyl)-1H-1,4-benzodiazepine-2,5-dione | 171819-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 4-tert-Butyl-7-chloro-9-(2'-pyridyl)-1H-1,4-benzodiazepine-2,5-dione
• 英文别名: 4-Tert-butyl-7-chloro-9-pyridin-2-yl-1,3-dihydro-1,4-benzodiazepine-2,5-dione
• CAS: 171819-75-3
• 化学式: C₁₈H₁₈ClN₃O₂
• 分子量: 343.813
• InChiKey: HEZACDCXIOHTSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-tert-Butyl-7-chloro-9-(2'-pyridyl)-1H-1,4-benzodiazepine-2,5-dione 在 palladium on activated charcoal ammonium formate 作用下， 以 乙醇 为溶剂， 反应 22.0h， 以68%的产率得到4-tert-Butyl-9-(2'-pyridyl)-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：

  5-氯-2-硝基苯甲酸 在 bis-triphenylphosphine-palladium(II) chloride 、 platinum on activated charcoal copper(l) iodide 、 氯化亚砜 、 硫酸 、 氢气 、 溴 、 sodium acetate 、 三氯化铁 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 、 甲苯 为溶剂， 25.0~80.0 ℃ 、344.73 kPa 条件下， 反应 88.34h， 生成 4-tert-Butyl-7-chloro-9-(2'-pyridyl)-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

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).