(7Z)-7-benzylidene-5-methoxy-2-methylthio-4-(pyrrolidin-1-yl)-5,7-dihydrofuro[3,4-d]pyrimidine | 1067892-87-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (7Z)-7-benzylidene-5-methoxy-2-methylthio-4-(pyrrolidin-1-yl)-5,7-dihydrofuro[3,4-d]pyrimidine
• 英文别名: (7Z)-7-benzylidene-5-methoxy-2-methylthio-4-pyrrolidin-1-yl-5,7-dihydrofuro[3,4-d]pyrimidine；(7Z)-7-benzylidene-5-methoxy-2-methylsulfanyl-4-pyrrolidin-1-yl-5H-furo[3,4-d]pyrimidine
• CAS: 1067892-87-8
• 化学式: C₁₉H₂₁N₃O₂S
• 分子量: 355.461
• InChiKey: HPWULTMNHNEPTB-OWBHPGMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 2-methylthio-6-phenylethynyl-4-(pyrrolidin-1-yl)pyrimidine-5-carbaldehyde 在 sodium methylate 作用下， 反应 1.0h， 以95%的产率得到(7Z)-7-benzylidene-5-methoxy-2-methylthio-4-(pyrrolidin-1-yl)-5,7-dihydrofuro[3,4-d]pyrimidine
  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

• 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.
• 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。