3,7-二羟基-2-(1,4-苯并二恶烷-6-基)色满-4-酮 | 79986-03-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 中文名称: 3,7-二羟基-2-(1,4-苯并二恶烷-6-基)色满-4-酮
• 中文别名: 2H-苯并三唑-4,5-二胺,2-甲基-
• 英文名称: trans-3,7-dihydroxy-3',4'-(ethylenedioxy)flavanone
• 英文别名: 3,7-dihydroxy-2-(1,4-benzodioxan-6-yl)chroman-4-one；(2S,3S)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-3,7-dihydroxy-2,3-dihydrochromen-4-one
• CAS: 79986-03-1
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: MGDQKWLRSIIJEI-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,3S)-2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-3-hydroxy-7-methoxymethoxy-chroman-4-one 在 Amberlyst 15 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以76%的产率得到3,7-二羟基-2-(1,4-苯并二恶烷-6-基)色满-4-酮
  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

文献信息

• Corsano; Proietti; Castagnino, Farmaco, Edizione Scientifica, 1983, vol. 38, # 4, p. 265 - 273
  作者：Corsano、Proietti、Castagnino、Strappaghetti

  DOI：——

  日期：——
• 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.