3-phenylcinnolin-4-amine | 33738-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-phenylcinnolin-4-amine
• 英文别名: 4-Amino-3-phenyl-cinnolin；3-Phenyl-4-amino-cinnolin；3-phenyl-cinnolin-4-ylamine
• CAS: 33738-83-9
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: FRTBYYJHPVDECM-UHFFFAOYSA-N

物化性质

• 沸点：
  420.7±37.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 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：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(三氟甲基)苯基肼 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 3-phenylcinnolin-4-amine
  参考文献：
  名称：

  A novel synthesis of 3,4-disubstituted cinnolines from o-trifluorophenyl hydrazones

  摘要：

  An efficient synthesis of 3-aryl-4-aminocinnolines from ortho-trifluoromethylphenyl hydrazones is described. The mechanism of the described transformation is likely to involve the formation of the quinone methide intermediate. The described procedure is easily adaptable to automated solid phase synthesis leading to analytically pure heterocycles. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00949-1

文献信息

• BF₃-Etherate-Promoted Cascade Reaction of 2-Alkynylanilines with Nitriles: One-Pot Assembly of 4-Amido-Cinnolines
  作者：Gopal Chandru Senadi、Babasaheb Sopan Gore、Wan-Ping Hu、Jeh-Jeng Wang

  DOI：10.1021/acs.orglett.6b01207

  日期：2016.6.17

  2-alkynylanilines is described. This method achieves the formation of two new C–N bonds through a reaction sequence of diazotization with t-BuONO, nucleophilic addition of the alkyne to the BF3-coordinated diazonium ion, followed by nitrile addition to the intermediary vinyl cation and hydrolysis. The method provides efficient and general access to a variety of 4-amido-cinnolines. Notable features of the method

  描述了BF 3-醚酸酯促进的腈与2-炔基苯胺的级联反应。该方法通过与t -BuONO进行重氮化，将炔烃亲核加到BF 3配位的重氮离子上，然后腈加成到中间乙烯基阳离子中并水解，从而实现了两个新的C–N键的形成。该方法提供了对各种4-氨基-丁二酸的有效且通用的途径。该方法的显着特征包括宽泛的官能团耐受性和避免使用过渡金属。
• Trifluoromethyl group in the synthesis of heterocyclic compounds: New and efficient synthesis of 3-aryl-4-aminocinnolines
  作者：Alexander S. Kiselyov

  DOI：10.1016/0040-4039(95)00005-w

  日期：1995.2

  A novel base induced transformation of hydrazones 3a-f derived from trifluoromethylaryl ketones and arylhydrazines was found to produce 3-aryl-4-aminocinnolines 4a-g in 52-75% yield. The initial step of the reaction is believed to involve abstraction of Hf from hydrazone.
• A novel synthesis of 3,4-disubstituted cinnolines from o-trifluorophenyl hydrazones
  作者：Alexander S. Kiselyov、Celia Dominguez

  DOI：10.1016/s0040-4039(99)00949-1

  日期：1999.7

  An efficient synthesis of 3-aryl-4-aminocinnolines from ortho-trifluoromethylphenyl hydrazones is described. The mechanism of the described transformation is likely to involve the formation of the quinone methide intermediate. The described procedure is easily adaptable to automated solid phase synthesis leading to analytically pure heterocycles. (C) 1999 Elsevier Science Ltd. All rights reserved.