4-氯-2-(甲硫基)-6-(1-哌啶基)-5-嘧啶甲醛 | 445040-60-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 4-氯-2-(甲硫基)-6-(1-哌啶基)-5-嘧啶甲醛
• 英文名称: 6-chloro-4-(piperidin-1-yl)-2-methylthiopyrimidine-5-carbaldehyde
• 英文别名: 6-chloro-2-methylsulfanyl-4-(1-piperidyl)pyrimidine-5-carbaldehyde；4-chloro-2-methylsulfanyl-6-(piperidin-1-yl)pyrimidine-5-carboxaldehyde；4-Chloro-2-(methylsulfanyl)-6-(1-piperidinyl)-5-pyrimidinecarbaldehyde；4-chloro-2-methylsulfanyl-6-piperidin-1-ylpyrimidine-5-carbaldehyde
• CAS: 445040-60-8
• 化学式: C₁₁H₁₄ClN₃OS
• mdl: MFCD02956233
• 分子量: 271.771
• InChiKey: QOOXHTLRSDRQKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-氯-2-(甲硫基)-6-(1-哌啶基)-5-嘧啶甲醛 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以57%的产率得到6-methylthio-4-(piperidin-1-yl)isoxazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Kaminskas; Dailide; Tumkevicius, Polish Journal of Chemistry, 2002, vol. 76, # 5, p. 725 - 728

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶-1-甲醛 、 4,6-二氯-二甲硫基嘧啶 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 以89%的产率得到4-氯-2-(甲硫基)-6-(1-哌啶基)-5-嘧啶甲醛
  参考文献：
  名称：

  Synthesis of 5,6-Disubstituted Thieno[2,3-d]pyrimidines from 4-Chloropyrimidines

  摘要：

  Facile reaction sequences for the preparation of 5,6-disubstituted thieno[2,3-d]pyrimidines starting with 4-chloropyrimidines have been developed. 4-Chloro-6-methoxypyrimidines were aroylated at the 5-positions via lithiation with LDA and subsequent treatment with benzaldehyde or N-methoxy-N-methylbenzamides to give aryl(4-chloro-6-methoxypyrimidin-5-yl)methanones. These pyrimidinyl ketones were transformed in one-pot into 5,6-disubstituted 4-methoxythieno[2,3-d]pyrimidines by a successive treatment with sodium sulfide, BrCH(2)EWGs, and sodium hydride. Lithiation of 4,6-dichloro-2-(methylsulfanyl)pyrimidine at the 5-position was followed by treatment with tertiary formamides to give 4-chloro-6-(dialkylamino)pyrimidine-5-carboxaldehydes, which could be transformed into 5,6-disubstituted 4-(dialkylamino)thieno[2,3-d]pyrimidines via aryl [4-chloro-6-(dialkylamino)pyrimidin-5-yl]methanones using the same one-pot thiophene ring forming sequence.

  DOI：

  10.3987/com-12-12463

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.
• Competitive formation of condensed azines and dihydropyridines in the reaction of ethyl 3,3-diaminoacrylate with o-halo carbaldehydes
  作者：I. I. Eliseev、D. V. Dar’in、S. I. Selivanov、P. S. Lobanov、A. A. Potekhin

  DOI：10.1007/s10593-008-0061-1

  日期：2008.4

  The reaction of ethyl 3,3-diaminoacrylate with quinoline-3-carbaldehydes and 3-nitrobenzaldehydes to give a dihydropyridine and condensed azine has been studied with respect to the number and reactivity of the halogen atoms in an ortho position to the formyl groups. For the series of quinoline-3-carbaldehydes it was found that the reaction course is determined by the number of chlorine atoms. 2-and 4-Chloroquinoline-3-carbaldehydes give dihydropyridines and a benzo[c][2,7-]naphthyridine is formed in the reaction with 2,4-dichloroquinoline-3-carbaldehyde. The main products in the case of nitrobenzaldehydes are dihydropyridines which points the deciding influence of the low electrophilicity of aromatic ring.
• Novel cyclocondensation of 2-acylethynyl-1-amino- and 2-alkoxycarbonylethynyl-1-amino-anthraquinones with pyridines
  作者：I. I. Barabanov

  DOI：10.1007/s10593-005-0083-x

  日期：2004.11
• ——
  作者：S. Tumkevicius、A. Kaminskas

  DOI：10.1023/a:1025114703659

  日期：——