4-tert-Butyl-7-chloro-1H-1,4-benzodiazepine-2,5-dione | 167689-85-2

• 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-1H-1,4-benzodiazepine-2,5-dione
• 英文别名: 7-chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione；4-Tert-butyl-7-chloro-1,3-dihydro-1,4-benzodiazepine-2,5-dione
• CAS: 167689-85-2
• 化学式: C₁₃H₁₅ClN₂O₂
• 分子量: 266.727
• InChiKey: OELNYTJWSYITDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-tert-Butyl-7-chloro-1H-1,4-benzodiazepine-2,5-dione 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 溴 、 sodium acetate 、 三氯化铁 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 54.0h， 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
• 作为产物：
  描述：

  5-氯-2-硝基苯甲酸 在 platinum on activated charcoal 氯化亚砜 、 硫酸 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 25.0~80.0 ℃ 、344.73 kPa 条件下， 反应 34.34h， 生成 4-tert-Butyl-7-chloro-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

• Methods for controlling undesirable plant species with benzodiazepine
  申请人：American Cyanamid Company

  公开号：US05438035A1

  公开（公告）日：1995-08-01

  There are provided methods for controlling undesirable plant species with benzodiazepine compounds of formulas I and II ##STR1## Further provided are herbicidal compositions comprising those compounds.

  提供了一种使用公式I和II的苯二氮卓类化合物控制不良植物物种的方法。还提供了包含这些化合物的除草剂组合物。
• Synthesis and Herbicidal Activity of 1<i>H</i>-1,4-Benzodiazepine-2,5-diones
  作者：Gary M. Karp、Mark C. Manfredi、Michael A. Guaciaro、Charles L. Ortlip、Pierre Marc、Iwona T. Szamosi

  DOI：10.1021/jf960669i

  日期：1997.2.1

  A series of 1H-1,4-benzodiazepine-2,5-diones, which have been found to inhibit photosystem II electron transport, were evaluated for their herbicidal activity. Many of the analogues tested exhibited moderate to good herbicidal activity both preemergence and postemergence. The structure-activity relationships were probed by substitution in both the benzene and diazepine ring. Among the variations investigated, it was found that maximal herbicidal activity was obtained by substitution at C-7 and C-9 in the aromatic portion and by bulky aliphatic substitution at N-4 while leaving N-1, C-6, and C-8 unsubstituted.
• US5438035A
  申请人：——

  公开号：US5438035A

  公开（公告）日：1995-08-01
• 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).