4-morpholin-4-yl-6-phenylethynylpyrimidine-5-carbaldehyde | 1067892-80-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-morpholin-4-yl-6-phenylethynylpyrimidine-5-carbaldehyde
• 英文别名: 4-Morpholin-4-yl-6-(2-phenylethynyl)pyrimidine-5-carbaldehyde；4-morpholin-4-yl-6-(2-phenylethynyl)pyrimidine-5-carbaldehyde
• CAS: 1067892-80-1
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: CISGADWAYYBCED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-morpholin-4-yl-6-phenylethynylpyrimidine-5-carbaldehyde 在 叔丁胺 作用下， 反应 24.0h， 以92%的产率得到7-phenyl-4-morpholin-4-ylpyrido[4,3-d]pyrimidine
  参考文献：
  名称：

  An Efficient One-Pot Synthetic Method for 2,4-Disubstituted 7-Arylpyrido[4,3-d]pyrimidines from 2,4-Disubstituted 6-(Arylethynyl)pyrimidine-5-carbaldehydes and tert-Butylamine

  摘要：

  2,4-二取代的6-(芳基-乙炔基)嘧啶-5-甲醛与叔丁胺发生意外的热环化，在不存在的情况下以良好的收率得到2,4-二取代的7-芳基吡啶并[4,3-d]嘧啶任何催化剂。分离了中间体化合物并讨论了可能的反应机理。

  DOI：

  10.1055/s-0028-1083500
• 作为产物：
  描述：

  4-氯-6-吗啉-5-嘧啶甲醛 、 苯乙炔 生成 4-morpholin-4-yl-6-phenylethynylpyrimidine-5-carbaldehyde
  参考文献：
  名称：

  碱性介质中乙炔醛与亚磷酸二甲酯的反应研究：膦酸酯-磷酸盐重排与5 - exo- dig环化反应

  摘要：

  在碱性介质中研究了各种炔醛与亚磷酸二甲酯的串联反应。已经表明，在起始材料的未活化的三键的情况下，发生了众所周知的Pudovik反应，随后发生了膦酸酯-磷酸盐的重排。另一方面，当起始材料的三键被吸电子杂环激活时，顺畅且区域选择性的串联5-外切-环化反应成为可能。

  DOI：

  10.1002/adsc.201200276

文献信息

• The First Tandem Acetalization/5-<i>exo</i>-<i>dig</i> Cyclization of 6-Phenylethynylpyrimidine-5-carbaldehydes: Efficient Synthesis of 5-Alkoxy-(7<i>Z</i>)-7-benzylidene-5<i>,</i>7<i>-</i>dihydrofuro[3,4-<i>d</i>]pyrimidines
  作者：Inga Cikotiene、Marius Morkunas、Dainius Motiejaitis、Simonas Rudys、Algirdas Brukstus

  DOI：10.1055/s-2008-1077824

  日期：——

  The first example of catalyst-free tandem acetalization/5-exo-dig cyclization reactions of 6-phenylethynylpyrimidine-5-carbaldehydes is presented. Efficient novel synthesis of 5,7-dihydrofuro[3,4-d]pyrimidine core is described.

  首次介绍了 6-苯基乙炔基嘧啶-5-羰基醛的无催化剂串联缩醛化/5-外-二羰基环化反应。介绍了 5,7-二氢呋喃并[3,4-d]嘧啶核的高效新型合成方法。
• Study on the cyclization of 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine: microwave versus thermal preparation of pyrido[4,3-d]pyrimidines
  作者：Inga Cikotiene、Visvaldas Kairys、Rita Buksnaitiene、Marius Morkunas、Simonas Rudys、Algirdas Brukstus、Miguel X. Fernandes

  DOI：10.1016/j.tet.2009.05.015

  日期：2009.7

  Thermal and microwave initiated cyclization of 2,4-disubstituted 6-arylethynylpyrimidine-5-carbaldehydes with tert-butylamine has been studied. A novel high-yielding preparation of 2,4-disubstituted 7-arylpyrido[4,3-d]pyrimidines has been developed. The intermediate compounds were isolated and possible mechanism of the reactions is discussed. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.
• Tandem reactions of 6-phenylethynylpyrimidine-5-carbaldehydes with alcohols: regioselective synthesis of 5-alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines and 5-alkoxy-7-phenyl-5H-pyrano[4,3-d]pyrimidines
  作者：Inga Cikotiene、Rita Buksnaitiene、Simonas Rudys、Marius Morkunas、Dainius Motiejaitis

  DOI：10.1016/j.tet.2009.10.108

  日期：2010.1

  An efficient and versatile tandem processes of acetalisation and cycloisomerization reactions have been developed for the reactions of 6-phenylethynylpyrimidine-5-carbaldehydes. The influence of the catalyst and role of the substituent in the position 4 of the pyrimidine ring have been studied. Regioselective synthesis of 5,7-dihydrofuro[3,4-d]pyrimidine and pyrano[4,3-d]pyrimidine cores is described. (C) 2009 Elsevier Ltd. All rights reserved.