(2R,3R)-2-(4-Bromo-phenyl)-3-hydroxy-chroman-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R,3R)-2-(4-Bromo-phenyl)-3-hydroxy-chroman-4-one
• 英文别名: (2R,3R)-2-(4-bromophenyl)-3-hydroxy-2,3-dihydrochromen-4-one
• 化学式: C₁₅H₁₁BrO₃
• 分子量: 319.155
• InChiKey: ZYIFKHMEFSDECI-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(2S,3R)-3-(4-Bromo-phenyl)-oxiranyl]-(2-hydroxy-phenyl)-methanone 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 122.0h， 生成 (2R,3R)-2-(4-Bromo-phenyl)-3-hydroxy-chroman-4-one
  参考文献：
  名称：

  Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides:  3-Hydroxychromanones and -flavanones versus 2-(1-Hydroxyalkyl)-3-coumaranones

  摘要：

  Competitive alpha and beta cyclization of 2'-hydroxychalcone epoxides affords 2-(alpha-hydroxybenzyl)-3-coumaranone and/or 3-hydroxyflavanones, which depends on the conditions employed. Epoxidation of 2'-hydroxychalcones by dimethyldioxirane followed by either base- or acid-catalyzed ring closure provides a novel, general, and efficient method for the synthesis of trans-3-hydroxyflavanones, which includes also the naturally occurring derivatives. Extension of this two-step procedure to 1-(2-hydroxyphenyl)-2-alken-1-ones was also accomplished. A strong preference for alpha cyclization was observed in the case of beta-unsubstituted or -monoalkylated alpha,beta-enones, while both 2,2-dimethyl-3-hydroxychromanones and 2-(1-hydroxy-1-methylethyl)-3-coumaranones were obtained from the beta,beta-dimethylated substrates.

  DOI：

  10.1021/jo960163z