threo-2-(α-hydroxybenzyl)-3-coumaranone | 14796-31-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: threo-2-(α-hydroxybenzyl)-3-coumaranone
• CAS: 14796-31-7
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: LSVSOTMKMNZYHC-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  以 水 、 乙腈 为溶剂， 生成 rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one 、 threo-2-(α-hydroxybenzyl)-3-coumaranone
  参考文献：
  名称：

  某些2'-羟基查尔酮环氧化物环化的动力学和机理以及随后的金酮水合物消除反应

  摘要：

  分析用于生成3-羟基黄烷酮的2'-羟基查耳酮环氧化物单阴离子和大部分生成水合物的一些6'-烷氧基取代的类似物环化的pH速率分布，得出速率系数，量化了α对β的偏好存在6'-取代基时环化。这些是根据可能导致偏爱的立体电子因素来考虑的。还报道了其中形成金酮和香豆香酮的金酮水合物随后反应的速率系数。

  DOI：

  10.1016/s0040-4020(01)92283-5

文献信息

• Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides:  3-Hydroxychromanones and -flavanones <i>versus</i> 2-(1-Hydroxyalkyl)-3-coumaranones
  作者：Tamás Patonay、Albert Lévai、Csaba Nemes、Tibor Timár、Gábor Tóth、Waldemar Adam

  DOI：10.1021/jo960163z

  日期：1996.1.1

  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.
• A convenient and general synthesis of trans-3-hydroxyflavanones from chalcones by dimethyldioxirane epoxidation and subsequent base-catalyzed cyclization
  作者：Tamás Patonay、Gábor Tóth、Waldemar Adam

  DOI：10.1016/s0040-4039(00)60674-3

  日期：1993.8

  2'-Hydroxychalcone epoxides were found to give trans-3-hydroxyflavanone and 2-(alpha-hydroxybenzyl)-3-coumaranone under basic conditions. Epoxidation of 2'-hydroxychalcones with dimethyldioxirane followed by treatment of tetrabutylammonium hydroxide provides a convenient and general method for the synthesis of trans-3-hydroxyflavanones.