5-chloro-2-nitro-N-(2-methyl-1-propen-1-yl)benzenamine | 424799-68-8

• 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: 5-chloro-2-nitro-N-(2-methyl-1-propen-1-yl)benzenamine
• 英文别名: 5-chloro-N-(2-methylprop-1-enyl)-2-nitroaniline
• CAS: 424799-68-8
• 化学式: C₁₀H₁₁ClN₂O₂
• 分子量: 226.663
• InChiKey: FCXBFECDRWJPLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-2-nitro-N-(2-methyl-1-propen-1-yl)benzenamine 在 巴拉松 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 1,10-菲罗啉 、 一氧化碳 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 70.0 ℃ 、607.99 kPa 条件下， 以29%的产率得到6-chloro-1,2-dihydro-2,2-dimethylquinoxaline
  参考文献：
  名称：

  A Novel Palladium-Catalyzed Synthesis of 1,2-Dihydroquinoxalines and 3,4-Dihydroquinoxalinones

  摘要：

  [GRAPHICS]Reactions of enamines, derived from 2-nitroanilines and alpha-substituted aldehydes, with carbon monoxide (6 atm) in the presence of a catalytic amount of bis(dibenzylideneacetone)palladium(0) (Pd(dba)(2)) and 1,3-bis(diphenylphosphino)propane (dppp) afford readily separated mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones. Addition of a catalytic amount of 1,10-phenanthroline to the reaction mixture substantially improved the yield of products.

  DOI：

  10.1021/ol025640g
• 作为产物：
  描述：

  2-硝基-5-氯苯胺 、 异丁醛 生成 5-chloro-2-nitro-N-(2-methyl-1-propen-1-yl)benzenamine
  参考文献：
  名称：

  N-烷氧基取代的2 H-苯并咪唑的合成

  摘要：

  的2-硝基治疗ñ - （2-甲基-1-丙烯-1-基）benzenamines钾叔丁醇在叔丁醇，接着添加亲电子试剂，得到的ñ -烷氧基-2- ħ -benzimidazoles。包括甲基碘，烯丙基溴，炔丙基溴，苄基溴和乙酰氯在内的亲电试剂的收率非常好，而1-碘-和2-碘-丁烷的收率却非常低。

  DOI：

  10.1016/j.tetlet.2017.11.007

文献信息

• A facile base-mediated synthesis of N-alkoxy-substituted benzimidazoles
  作者：Nurul H. Ansari、Arica L. Jordan、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2017.06.063

  日期：2017.8

  Base mediated cyclization of enamines derived from condensation of 2-nitroanilines with α-branched aldehydes, in the presence of an electrophile, affords N-alkoxy-substituted benzimidazoles with or without an oxygenate side chain in the 2-position.

  在亲电子试剂的存在下，碱介导的由2-硝基苯胺与α-支化醛缩合衍生的烯胺的环化，可得到在2-位带有或不带有氧化侧链的N-烷氧基取代的苯并咪唑。
• A Novel Palladium-Catalyzed Synthesis of 1,2-Dihydroquinoxalines and 3,4-Dihydroquinoxalinones
  作者：Björn C. G. Söderberg、Jeffery M. Wallace、Joaquín Tamariz

  DOI：10.1021/ol025640g

  日期：2002.4.1

  [GRAPHICS]Reactions of enamines, derived from 2-nitroanilines and alpha-substituted aldehydes, with carbon monoxide (6 atm) in the presence of a catalytic amount of bis(dibenzylideneacetone)palladium(0) (Pd(dba)(2)) and 1,3-bis(diphenylphosphino)propane (dppp) afford readily separated mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones. Addition of a catalytic amount of 1,10-phenanthroline to the reaction mixture substantially improved the yield of products.
• Palladium-catalyzed synthesis of quinoxaline derivatives
  作者：Jeffery M. Wallace、Björn C.G. Söderberg、Joaquín Tamariz、Novruz G. Akhmedov、Mathew T. Hurley

  DOI：10.1016/j.tet.2008.07.083

  日期：2008.10

  A palladium-catalyzed reductive N-heteroannulation of enamines derived from 2-nitrobenzenamines forming mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalin-2-ones is described. The reactions are performed using bis(dibenzylideneacetone)palladium(0), 1,3-bis(diphenylphosphino)propane, and 1,10-phenanthroline in DMF under 6 atm of carbon monoxide at 70 degrees C. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of N-alkoxy-substituted 2H-benzimidazoles
  作者：Nurul H. Ansari、Björn C.G. Söderberg

  DOI：10.1016/j.tetlet.2017.11.007

  日期：2017.12

  Treatment of 2-nitro-N-(2-methyl-1-propen-1-yl)benzenamines with potassium tert-butoxide in tert-butanol followed by the addition of an electrophile affords N-alkoxy-2H-benzimidazoles. Electrophiles including methyl iodide, allylic bromides, propargylic bromides, benzyl bromide, and acetyl chloride gave good to excellent yields of product while 1-iodo- and 2-iodo-butane afforded very low yields.

  的2-硝基治疗ñ - （2-甲基-1-丙烯-1-基）benzenamines钾叔丁醇在叔丁醇，接着添加亲电子试剂，得到的ñ -烷氧基-2- ħ -benzimidazoles。包括甲基碘，烯丙基溴，炔丙基溴，苄基溴和乙酰氯在内的亲电试剂的收率非常好，而1-碘-和2-碘-丁烷的收率却非常低。