8-bromo-6-chloro-2-methylchroman-4-one | 1154547-56-4

• 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: 8-bromo-6-chloro-2-methylchroman-4-one
• 英文别名: 8-Bromo-6-chloro-2-methyl-2,3-dihydrochromen-4-one
• CAS: 1154547-56-4
• 化学式: C₁₀H₈BrClO₂
• 分子量: 275.529
• InChiKey: AEBVOCFHFIVZQL-UHFFFAOYSA-N

物化性质

• 沸点：
  380.5±42.0 °C(predicted)
• 密度：
  1.602±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3'-溴-5'-氯-2'-羟基苯乙酮 、 乙醛 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以28%的产率得到8-bromo-6-chloro-2-methylchroman-4-one
  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.