benzyl-(2-chloro-5-nitrophenyl)amine | 906371-85-5

• 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: benzyl-(2-chloro-5-nitrophenyl)amine
• 英文别名: N-benzyl-2-chloro-5-nitroaniline
• CAS: 906371-85-5
• 化学式: C₁₃H₁₁ClN₂O₂
• 分子量: 262.696
• InChiKey: HICXTYNFKLCPST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  benzyl-(2-chloro-5-nitrophenyl)amine 在 双(乙腈)氯化钯(II) 、 2-二环己基磷-2,4,6-三异丙基联苯 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 16.5h， 生成 1-benzyl-6-nitro-2-phenyl-1H-indole
  参考文献：
  名称：

  Efficient Access to Azaindoles and Indoles

  摘要：

  An expedient, catalytic method for the synthesis of diverse azaindoles and indoles, starting from readily available and inexpensive starting materials, is described. Conditions were developed for effective reductive alkylation of electron-deficient o-chloroarylamines, substrates previously viewed as poor partners in this reaction. The derived N-alkylated o-chloroarylamines were elaborated to N-alkylazaindoles and N-alkylindoles via a novel one-pot process comprising copper-free Sonogashira alkynylation and a base-mediated indolization reaction.

  DOI：

  10.1021/ol061232r
• 作为产物：
  描述：

  2-氯-5-硝基苯胺 、 苯甲醛 在 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 醋酸异丙酯 为溶剂， 反应 0.17h， 以84%的产率得到benzyl-(2-chloro-5-nitrophenyl)amine
  参考文献：
  名称：

  Efficient Access to Azaindoles and Indoles

  摘要：

  An expedient, catalytic method for the synthesis of diverse azaindoles and indoles, starting from readily available and inexpensive starting materials, is described. Conditions were developed for effective reductive alkylation of electron-deficient o-chloroarylamines, substrates previously viewed as poor partners in this reaction. The derived N-alkylated o-chloroarylamines were elaborated to N-alkylazaindoles and N-alkylindoles via a novel one-pot process comprising copper-free Sonogashira alkynylation and a base-mediated indolization reaction.

  DOI：

  10.1021/ol061232r

文献信息

• Efficient Access to Azaindoles and Indoles
  作者：Mark McLaughlin、Michael Palucki、Ian W. Davies

  DOI：10.1021/ol061232r

  日期：2006.7.1

  An expedient, catalytic method for the synthesis of diverse azaindoles and indoles, starting from readily available and inexpensive starting materials, is described. Conditions were developed for effective reductive alkylation of electron-deficient o-chloroarylamines, substrates previously viewed as poor partners in this reaction. The derived N-alkylated o-chloroarylamines were elaborated to N-alkylazaindoles and N-alkylindoles via a novel one-pot process comprising copper-free Sonogashira alkynylation and a base-mediated indolization reaction.