4-氯-6-(吲哚啉-1-基)嘧啶 | 293292-33-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-氯-6-(吲哚啉-1-基)嘧啶
• 英文名称: 1-(6-Chloropyrimidin-4-yl)indoline
• 英文别名: 4-chloro-6-(indolin-1-yl)pyrimidine；1-(6-Chloro-4-pyrimidinyl)indoline；1-(6-chloropyrimidin-4-yl)-2,3-dihydroindole
• CAS: 293292-33-8
• 化学式: C₁₂H₁₀ClN₃
• mdl: MFCD13561829
• 分子量: 231.685
• InChiKey: RSEMHHFXNIKRQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-氯-6-(吲哚啉-1-基)嘧啶 、 间溴三氟甲苯 在 (2,2'-bipyridine)nickel(II) dibromide 、 四丁基溴化铵 、 1,2-二溴乙烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 以77%的产率得到1-[6-(3-(trifluoromethyl)phenyl)pyrimidin-4-yl]indoline
  参考文献：
  名称：

  An Electrochemical Synthesis of Functionalized Arylpyrimidines from 4-Amino-6-Chloropyrimidines and Aryl Halides

  摘要：

  通过 4-氨基-6-氯嘧啶与官能化芳基卤化物之间的电化学还原交叉偶联反应，在温和条件下制备了一系列新型 4-氨基-6-芳基嘧啶。该工艺采用牺牲性铁阳极和镍（II）催化剂，能以中等至高产率生成偶联产物。

  DOI：

  10.3390/molecules16075550
• 作为产物：
  描述：

  4,6-二氯嘧啶 、 吲哚啉 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以89%的产率得到4-氯-6-(吲哚啉-1-基)嘧啶
  参考文献：
  名称：

  Selective mono-amination of dichlorodiazines

  摘要：

  A mild, easy-to-perform, and versatile method for the formation of aminochlorodiazines from reaction of several types of dichlorodiazines (i.e., pyridazines, pyrimidines, and pyrazines) with primary or secondary amines in ethanol in the presence of triethylamine as a base, is described. The methodology is general and efficient despite noticeable difference in reactivity between diazines. While dichloropyridazine and dichloropyrazine require several hours of heating at reflux for the reaction to proceed, dichloropyrimidines reach completion within minutes at room temperature. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.056

文献信息

• PYRIMIDINE COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1161428B1

  公开（公告）日：2003-05-28
• US6716831B1
  申请人：——

  公开号：US6716831B1

  公开（公告）日：2004-04-06
• [EN] PYRIMIDINE COMPOUNDS<br/>[FR] COMPOSES PYRIMIDINE
  申请人：ASTRAZENECA AB

  公开号：WO2000053595A1

  公开（公告）日：2000-09-14

  A pyrimidine derivative of formula (I) or (I'): wherein: Rx is a substituent as defined within; Q¿1? is optionally substituted phenyl, and Q1 bears a substituent of formula (Ia) wherein: X, Y?1, Y2¿, Z, n, and m are as defined within; -NQ¿2? is an optionally substituted heterocyclic moiety containing one nitrogen heteroatom and optionally containing a further heteroatom; or a pharmaceutically acceptable salt in vivo hydrolysable ester thereof; are useful as anti-cancer agents. Processes for their manufacture and pharmaceutical compositions containing them are described.
• Selective mono-amination of dichlorodiazines
  作者：Stéphane Sengmany、Julie Lebre、Erwan Le Gall、Eric Léonel

  DOI：10.1016/j.tet.2015.05.056

  日期：2015.7

  A mild, easy-to-perform, and versatile method for the formation of aminochlorodiazines from reaction of several types of dichlorodiazines (i.e., pyridazines, pyrimidines, and pyrazines) with primary or secondary amines in ethanol in the presence of triethylamine as a base, is described. The methodology is general and efficient despite noticeable difference in reactivity between diazines. While dichloropyridazine and dichloropyrazine require several hours of heating at reflux for the reaction to proceed, dichloropyrimidines reach completion within minutes at room temperature. (C) 2015 Elsevier Ltd. All rights reserved.
• An Electrochemical Synthesis of Functionalized Arylpyrimidines from 4-Amino-6-Chloropyrimidines and Aryl Halides
  作者：Stéphane Sengmany、Erwan Le Gall、Eric Léonel

  DOI：10.3390/molecules16075550

  日期：——

  A range of novel 4-amino-6-arylpyrimidines has been prepared under mild conditions by an electrochemical reductive cross-coupling between 4-amino-6-chloro-pyrimidines and functionalized aryl halides. The process, which employs a sacrificial iron anode in conjunction with a nickel(II) catalyst, allows the formation of coupling products in moderate to high yields.

  通过 4-氨基-6-氯嘧啶与官能化芳基卤化物之间的电化学还原交叉偶联反应，在温和条件下制备了一系列新型 4-氨基-6-芳基嘧啶。该工艺采用牺牲性铁阳极和镍（II）催化剂，能以中等至高产率生成偶联产物。