2-methylthio-4-(morpholin-4-yl)-6-phenylethynyl-pyrimidine-5-carbaldehyde | 1067892-75-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methylthio-4-(morpholin-4-yl)-6-phenylethynyl-pyrimidine-5-carbaldehyde
• 英文别名: 2-methylthio-4-morpholin-4-yl-6-phenylethynylpyrimidine-5-carbaldehyde；2-Methylsulfanyl-4-morpholin-4-yl-6-(2-phenylethynyl)pyrimidine-5-carbaldehyde
• CAS: 1067892-75-4
• 化学式: C₁₈H₁₇N₃O₂S
• 分子量: 339.418
• InChiKey: JUBIVSGJVGLSBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  80.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methylthio-4-(morpholin-4-yl)-6-phenylethynyl-pyrimidine-5-carbaldehyde 在 叔丁胺 作用下， 反应 24.0h， 以95%的产率得到2-(methylthio)-4-morpholin-1-yl-7-phenylpyrido[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：

  苯乙炔 、 2-(methylthio)-4-chloro-6-morpholin-4-ylpyrimidine-5-carboxaldehyde 生成 2-methylthio-4-(morpholin-4-yl)-6-phenylethynyl-pyrimidine-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

• Rapid access to benzo-annelated heterocycles, naphthalenes, and polysubstituted benzenes through a novel benzannulation reaction
  作者：Inga Cikotiene、Rita Buksnaitiene、Rokas Sazinas

  DOI：10.1016/j.tet.2010.11.073

  日期：2011.1

  mercaptoacetate triggered benzannulation reaction is described. The precursors are heterocyclic, aromatic or acyclic compounds bearing a carbonyl group at ortho position to an internal alkyne. The methodology does not require transition-metal catalysts and moreover it is general for the preparation of wide range of benzo-annelated heterocycles, naphthalenes and benzenes.

  描述了新颖，高效，强大的巯基乙酸甲酯触发苯环化反应。前体是在内部炔烃的邻位带有羰基的杂环，芳族或无环化合物。该方法不需要过渡金属催化剂，而且通常用于制备各种苯并-退火的杂环，萘和苯。
• 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。
• The First and Efficient Synthesis of 7-Aryl-6-methoxycarbonylquinazolines via Unexpected Reaction of 6-Arylethynylpyrimidine-5-carbaldehydes and Methyl Mercaptoacetate
  作者：Inga Cikotiene、Marius Morkunas

  DOI：10.1055/s-0028-1087514

  日期：——

  A highly concise synthesis of 7-aryl-6-methoxycarbonylquinazolines via reaction of 6-arylethynylpyrimidine-5-carbaldehydes and methyl mercaptoacetate is described.

  描述了通过 6-芳基乙炔基嘧啶-5-甲醛和巯基乙酸甲酯的反应高度简洁地合成 7-芳基-6-甲氧基羰基喹唑啉。
• 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.