2-amino-3-phenylindole | 55875-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-amino-3-phenylindole
• 英文别名: 3-phenyl-indol-2-ylamine；3-phenyl-1H-indol-2-amine
• CAS: 55875-30-4
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: FWNNKDOSGRZAPP-UHFFFAOYSA-N

物化性质

• 沸点：
  439.4±33.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-amino-3-phenylindole 在 sodium nitrite 、 sodium carbonate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 3.0h， 以50%的产率得到2-diazo-3-phenyl-2H-indole
  参考文献：
  名称：

  2-Diazo-2H-indoles

  摘要：

  2-Diazo-2H-indoles were prepared by diazotization of the corresponding 1H-indol-2-amines and subsequent neutralization. On the basis of NMR data and ab initio, and semiempirical calculations, we suggest that the zwitterionic form A is the most representative structure for 2-diazo-2H-indoles. In fact, spectral data are compatible with a IH-indole structure, and the fully optimized molecules gave distances in agreement with those reported for the anion obtained from 1H-indole. The calculated charges are compatible with a zwitterionic structure in which the negative charge is mainly located at the ring N-atom at variance with the case of diazopyrroles and 3-diazo-3H-indoles where the negative charge is essentially located on the ipso C-atom.

  DOI：

  10.1002/1522-2675(20010815)84:8<2212::aid-hlca2212>3.0.co;2-s
• 作为产物：
  描述：

  1-(pyridine-2-carbonyl)-3-phenylindole 在 亚硝酸特丁酯 、 copper dichloride 、 hydrazine hydrate 、 FeCl₃/C 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 11.0h， 以91%的产率得到2-amino-3-phenylindole
  参考文献：
  名称：

  一种制备2-氨基吲哚衍生物的方法

  摘要：

  本发明公开了一种制备2‑氨基吲哚衍生物的方法。本发明使用吡啶甲酰基吲哚为起始物，原料易得，种类广泛；利用本发明方法得到的产物类型多样，用途广泛，既可直接使用，又可用于合成药物；此外，本发明公开的方法步骤简单、反应条件温和、目标产物的收率高、污染小、反应操作和后处理过程简单，适合于工业化生产。

  公开号：

  CN108440496B

文献信息

• Antiinflammatory 2-imino-indolines and their pharmaceutical compositions
  申请人：Gruppo Lepetit S.p.A.

  公开号：US03984563A1

  公开（公告）日：1976-10-05

  Compounds with antiinflammatory, analgesic and CNS depressant activity having the following general formula ##SPC1## Wherein R represents hydrogen or methoxy; R.sub.1 represents hydrogen; lower alkyl; lower alkyl substituted with a group carboxy, carbo(lower alkoxy) or carbamyl; phenyl; benzyl, lower aliphatic acyl; benzoyl; benzoyl substituted with a halo group; R.sub.2 represents hydrogen; lower alkyl; carbo(lower alkoxy); carbamyl; phenylcarbamyl; lower aliphatic acyl; benzoyl; benzoyl substituted with a halo group, R.sub.3 represents halo; lower alkyl; lower alkyl substituted with a group selected from carboxy, carbo(lower alkoxy), carbamyl, halo, amino, mono and di-lower alkylamino, phthalimido and morpholino; phenyl; phenyl substituted with a group selected from lower alkoxy, halo, nitro, amino and acetamido; R.sub.4 represents hydrogen or lower alkyl; with the proviso that when simultaneously R.sub.1 represents hydrogen, methyl, phenyl, benzyl, acetyl or benzoyl, R.sub.2 represents hydrogen, lower alkyl or acetyl, R.sub.3 represents lower alkyl or phenyl, R.sub.4 must be different from hydrogen and methyl; Or R.sub.3 and R.sub.4 taken together with the adjacent carbon atom may represent a 5-6 membered alicyclic ring.

  具有抗炎、镇痛和中枢神经系统抑制活性的化合物具有以下一般化学式##SPC1##其中R代表氢或甲氧基；R.sub.1代表氢；较低的烷基；带有羧基、羧基（较低的烷氧基）或氨基甲酰基取代的较低烷基；苯基；苄基；较低脂肪酰基；苯甲酰基；带有卤原子取代的苯甲酰基；R.sub.2代表氢；较低的烷基；羧基（较低的烷氧基）；氨基甲酰基；苯基氨基甲酰基；较低脂肪酰基；苯甲酰基；带有卤原子取代的苯甲酰基，R.sub.3代表卤原子；较低的烷基；带有羧基、羧基（较低的烷氧基）、氨基甲酰基、卤原子、氨基、单取代和双取代的较低烷基氨基、邻苯二甲酰亚胺基和吗啉基等基团取代的较低烷基；苯基；带有较低烷氧基、卤原子、硝基、氨基和乙酰氨基等基团取代的苯基；R.sub.4代表氢或较低烷基；但当同时R.sub.1代表氢、甲基、苯基、苄基、乙酰基或苯甲酰基时，R.sub.2代表氢、较低烷基或乙酰基，R.sub.3代表较低烷基或苯基，R.sub.4必须与氢和甲基不同；或者R.sub.3和R.sub.4与相邻的碳原子一起可以代表一个5-6元杂环环。
• 2-Diazoindoles: building blocks for the synthesis of antineoplastic agents
  作者：Paola Barraja、Patrizia Diana、Antonino Lauria、Anna Maria Almerico、Gaetano Dattolo、Girolamo Cirrincione

  DOI：10.1016/s0014-827x(01)01175-2

  日期：2002.2

  2-Diazoindoles were prepared by diazotization of the corresponding 2-aminoindoles followed by neutralisation. 2-Diazoindoles were utilised for the synthesis of 2-triazenoindoles, indolo[2,1-d][1,2,3,5]tetrazines and indolo[2,1-c][1,2,4]triazines. Most of these compounds exhibited in vitro antiproliferative activity. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• TMSOTf-Catalyzed Reactions of <i>N</i>-Arylynamides with Sulfilimines To Construct 2-Aminoindoles and α-Arylated Amidines
  作者：Xiao-Na Wang、Yanan Wang、Nanfang Wang、Jinyue Chen、Chaofan Qi、Junbiao Chang

  DOI：10.1021/acs.joc.3c02342

  日期：2024.1.19
• 2-Diazo-2H-indoles
  作者：Paola Barraja、Patrizia Diana、Antonino Lauria、Anna Maria Almerico、Gaetano Dattolo、Girolamo Cirrincione

  DOI：10.1002/1522-2675(20010815)84:8<2212::aid-hlca2212>3.0.co;2-s

  日期：2001.8.15

  2-Diazo-2H-indoles were prepared by diazotization of the corresponding 1H-indol-2-amines and subsequent neutralization. On the basis of NMR data and ab initio, and semiempirical calculations, we suggest that the zwitterionic form A is the most representative structure for 2-diazo-2H-indoles. In fact, spectral data are compatible with a IH-indole structure, and the fully optimized molecules gave distances in agreement with those reported for the anion obtained from 1H-indole. The calculated charges are compatible with a zwitterionic structure in which the negative charge is mainly located at the ring N-atom at variance with the case of diazopyrroles and 3-diazo-3H-indoles where the negative charge is essentially located on the ipso C-atom.
• 一种制备2-氨基吲哚衍生物的方法
  申请人：苏州大学

  公开号：CN108440496B

  公开（公告）日：2019-09-10

  本发明公开了一种制备2‑氨基吲哚衍生物的方法。本发明使用吡啶甲酰基吲哚为起始物，原料易得，种类广泛；利用本发明方法得到的产物类型多样，用途广泛，既可直接使用，又可用于合成药物；此外，本发明公开的方法步骤简单、反应条件温和、目标产物的收率高、污染小、反应操作和后处理过程简单，适合于工业化生产。

表征谱图