2-methylthio-6-phenylethynyl-4-(pyrrolidin-1-yl)pyrimidine-5-carbaldehyde | 1067892-70-9

• 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-6-phenylethynyl-4-(pyrrolidin-1-yl)pyrimidine-5-carbaldehyde
• 英文别名: 2-Methylsulfanyl-4-(2-phenylethynyl)-6-pyrrolidin-1-ylpyrimidine-5-carbaldehyde
• CAS: 1067892-70-9
• 化学式: C₁₈H₁₇N₃OS
• 分子量: 323.418
• InChiKey: KDHXLWYDRQGPDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 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：
  71.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methylthio-6-phenylethynyl-4-(pyrrolidin-1-yl)pyrimidine-5-carbaldehyde 在 叔丁胺 作用下， 反应 24.0h， 以89%的产率得到2-methylthio-7-phenyl-4-pyrrolidin-1-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：

  苯乙炔 、 4-氯-2-甲基磺酰基-6-吡咯烷-1-基-嘧啶-5-甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到2-methylthio-6-phenylethynyl-4-(pyrrolidin-1-yl)pyrimidine-5-carbaldehyde
  参考文献：
  名称：

  The First Tandem Acetalization/5-exo-dig Cyclization of 6-Phenylethynylpyrimidine-5-carbaldehydes: Efficient Synthesis of 5-Alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines

  摘要：

  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。

  DOI：

  10.1055/s-2008-1077824

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。
• An Efficient One-Pot Synthetic Method for 2,4-Disubstituted 7-Arylpyrido[4,3-<i>d</i>]pyrimidines from 2,4-Disubstituted 6-(Arylethynyl)pyrimidine-5-carbaldehydes and <i>tert</i>-Butylamine
  作者：Inga Cikotiene、Marius Morkunas、Simonas Rudys、Rita Buksnaitiene、Algirdas Brukstus

  DOI：10.1055/s-0028-1083500

  日期：——

  Unexpected thermal cyclization of 2,4-disubstituted 6-(aryl-ethynyl)pyrimidine-5-carbaldehydes with tert-butylamine proceeded to give 2,4-disubstituted 7-arylpyrido[4,3-d]pyrimidines in good yields in the absence of any catalysts. The intermediate compounds were isolated and possible mechanism of the reactions is discussed.

  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。
• 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。
• 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.