1,3-dibenzyl-7-bromo-9-chloro-5-methyl-2,3,4,5-tetrahydro-1H-chromeno[4,3-d]pyrimidine | 1392284-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1,3-dibenzyl-7-bromo-9-chloro-5-methyl-2,3,4,5-tetrahydro-1H-chromeno[4,3-d]pyrimidine
• 英文别名: 1,3-dibenzyl-7-bromo-9-chloro-5-methyl-4,5-dihydro-2H-chromeno[4,3-d]pyrimidine
• CAS: 1392284-03-5
• 化学式: C₂₆H₂₄BrClN₂O
• 分子量: 495.846
• InChiKey: UAQUPMDCFAXWQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-bromo-6-chloro-2-methylchroman-4-one 、 N-methylenebenzylamine 在 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以15%的产率得到1,3-dibenzyl-7-bromo-9-chloro-5-methyl-2,3,4,5-tetrahydro-1H-chromeno[4,3-d]pyrimidine
  参考文献：
  名称：

  Proline-mediated formation of novel chroman-4-one tetrahydropyrimidines

  摘要：

  Novel tricyclic N-benzylated chroman-4-one tetrahydropyrimidine derivatives have been prepared through a multi-component reaction between various 2-substituted chroman-4-one derivatives, N-methylenebenzylamine and a catalytic amount of proline under mild reaction conditions. The tricyclic structure of 1a was determined by NMR spectroscopy and confirmed by X-ray crystallography. An additional product, 2a, was isolated from the reaction mixture and its structure and conformation were determined by a combination of theoretical (Monte Carlo conformational search) and NMR-based (NOE and (3)J(HH) couplings) conformational analysis. The NMR analysis revealed one preferred geometry for 1a and 2a in CHCl3 solution. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.077

文献信息

• Proline-mediated formation of novel chroman-4-one tetrahydropyrimidines
  作者：Maria Fridén-Saxin、Tina Seifert、Lars Kristian Hansen、Morten Grøtli、Mate Erdelyi、Kristina Luthman

  DOI：10.1016/j.tet.2012.06.077

  日期：2012.9

  Novel tricyclic N-benzylated chroman-4-one tetrahydropyrimidine derivatives have been prepared through a multi-component reaction between various 2-substituted chroman-4-one derivatives, N-methylenebenzylamine and a catalytic amount of proline under mild reaction conditions. The tricyclic structure of 1a was determined by NMR spectroscopy and confirmed by X-ray crystallography. An additional product, 2a, was isolated from the reaction mixture and its structure and conformation were determined by a combination of theoretical (Monte Carlo conformational search) and NMR-based (NOE and (3)J(HH) couplings) conformational analysis. The NMR analysis revealed one preferred geometry for 1a and 2a in CHCl3 solution. (C) 2012 Elsevier Ltd. All rights reserved.