(cyclohexylmethyl)(2,4-dinitrophenyl)amine | 177721-95-8

• 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: (cyclohexylmethyl)(2,4-dinitrophenyl)amine
• 英文别名: N-Cyclohexylmethyl-2,4-dinitroaniline；N-(cyclohexylmethyl)-2,4-dinitroaniline
• CAS: 177721-95-8
• 化学式: C₁₃H₁₇N₃O₄
• 分子量: 279.296
• InChiKey: HOIXDOCOXWSDJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环己烷基甲醛 、 2,4-二硝基苯胺 在 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 0.34h， 以92%的产率得到(cyclohexylmethyl)(2,4-dinitrophenyl)amine
  参考文献：
  名称：

  Facile Reductive Amination of Aldehydes with Electron-Deficient Anilines by Acyloxyborohydrides in TFA: Application to a Diazaindoline Scale-Up

  摘要：

  A scale-up of diazaindoline 1 was achieved in four stages and 32% overall yield. The key step involved rapid reductive amination of aldehyde 8 with aniline 5 by sodium triacetoxyborohydride (STAB-H) and TFA followed by ring closure of intermediate amine 9 to compound 1 in the same pot. These reaction conditions were also applied to facile reductive aminations with anilines known to have little reactivity under STAB-H/AcOH conditions. Spectral data supported the tris(trifluoroacetoxy)borohydride anion (16) as the active reducing agent.

  DOI：

  10.1021/jo900157z

文献信息

• Facile Reductive Amination of Aldehydes with Electron-Deficient Anilines by Acyloxyborohydrides in TFA: Application to a Diazaindoline Scale-Up
  作者：Eric E. Boros、James B. Thompson、Subba R. Katamreddy、Andrew J. Carpenter

  DOI：10.1021/jo900157z

  日期：2009.5.1

  A scale-up of diazaindoline 1 was achieved in four stages and 32% overall yield. The key step involved rapid reductive amination of aldehyde 8 with aniline 5 by sodium triacetoxyborohydride (STAB-H) and TFA followed by ring closure of intermediate amine 9 to compound 1 in the same pot. These reaction conditions were also applied to facile reductive aminations with anilines known to have little reactivity under STAB-H/AcOH conditions. Spectral data supported the tris(trifluoroacetoxy)borohydride anion (16) as the active reducing agent.