1,3-dibenzyl-7-bromo-9-chloro-4-(2-(1-tosyl-1H-indol-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-chromeno[4,3-d]pyrimidine | 1392284-04-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1,3-dibenzyl-7-bromo-9-chloro-4-(2-(1-tosyl-1H-indol-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-chromeno[4,3-d]pyrimidine
• 英文别名: 1,3-dibenzyl-7-bromo-9-chloro-4-[2-[1-(4-methylphenyl)sulfonylindol-3-yl]ethyl]-4,5-dihydro-2H-chromeno[4,3-d]pyrimidine
• CAS: 1392284-04-6
• 化学式: C₄₂H₃₇BrClN₃O₃S
• 分子量: 779.197
• InChiKey: FYNRIIKIQQFZJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  51
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(1-tosyl-1H-indol-3-yl)propanal 、 3'-溴-5'-氯-2'-羟基苯乙酮 在 N,N-二异丙基乙胺 、 L-脯氨酸 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 49.0h， 生成 1,3-dibenzyl-7-bromo-9-chloro-4-(2-(1-tosyl-1H-indol-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-chromeno[4,3-d]pyrimidine 、 1,3-dibenzyl-7-bromo-9-chloro-5-(2-(1-tosyl-1H-indol-3-yl)ethyl)-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.