(E)-2'-hydroxychalcone epoxide | 129878-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2'-hydroxychalcone epoxide
• 英文别名: 2'-hydroxychalcone epoxide；(2-hydroxyphenyl)-[(2S,3R)-3-phenyloxiran-2-yl]methanone
• CAS: 129878-47-3
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: WTHRQTPREPZROJ-HUUCEWRRSA-N

物化性质

• 沸点：
  403.5±45.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2'-hydroxychalcone epoxide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以71%的产率得到rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-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
• 作为产物：
  描述：

  (2E)-1-(2-羟基苯基)-3-苯基-2-丙烯-1-酮 在 sodium acetate 、 二甲基二环氧乙烷 、 溶剂黄146 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 25.0h， 以60%的产率得到(E)-2'-hydroxychalcone epoxide
  参考文献：
  名称：

  类黄酮环氧化物。第20部分。二甲基二环氧乙烷（DMD）与类黄酮化合物的一些异常反应

  摘要：

  二甲基二环氧乙烷（DMD）通常以丙酮溶液的形式被证明是一种极好的环氧化剂。观察到，取决于反应混合物的pH和底物中存在的β-芳烃环的类型，可以得到2'-羟基查耳酮环氧化物或反式-2,3-二氢黄酮醇。使用这种方法，与通过最常用的Algar-Flynn-Oyamada反应合成方法相比，合成反式-2,3-二氢黄酮醇的产率要好得多。用DMD处理黄酮醇14和新型异金酮21均得到不同寻常的产物，而不是预期的环氧化物，但是，假定在反应过程中形成了环氧化物。

  DOI：

  10.1016/s0040-4020(97)00506-1

文献信息

• Chawla, H. M.; Chakrabarty, Kakoli; Prakash, Anil, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 6, p. 507 - 508
  作者：Chawla, H. M.、Chakrabarty, Kakoli、Prakash, Anil、Chibber, S. S.

  DOI：——

  日期：——
• Adam, Waldemar; Hadjiarapoglou, Lazaros; Smerz, Alex, Chemische Berichte, 1991, vol. 124, # 1, p. 227 - 232
  作者：Adam, Waldemar、Hadjiarapoglou, Lazaros、Smerz, Alex

  DOI：——

  日期：——
• Gupta, D. R.; Kamaluddin; Naithani, Shobha, Polish Journal of Chemistry, 1990, vol. 64, # 7, p. 747 - 751
  作者：Gupta, D. R.、Kamaluddin、Naithani, Shobha

  DOI：——

  日期：——
• Flavonoid epoxides. Part 20. Some unusual reactions of dimethyldioxirane (DMD) with flavonoid compounds
  作者：Anthony J. Burke、W. Ivo O'Sullivan

  DOI：10.1016/s0040-4020(97)00506-1

  日期：1997.6

  either the 2′-hydroxychalcone epoxide or the trans-2,3-dihydroflavonol could be obtained depending on the pH of the reaction mixture and the type of β-arene ring present in the substrate. Using this methodology trans-2,3-dihydroflavonols can be synthesised in far better yields than by the most commonly used method for their synthesis, that of the Algar-Flynn-Oyamada reaction. Treatment of both flavonol

  二甲基二环氧乙烷（DMD）通常以丙酮溶液的形式被证明是一种极好的环氧化剂。观察到，取决于反应混合物的pH和底物中存在的β-芳烃环的类型，可以得到2'-羟基查耳酮环氧化物或反式-2,3-二氢黄酮醇。使用这种方法，与通过最常用的Algar-Flynn-Oyamada反应合成方法相比，合成反式-2,3-二氢黄酮醇的产率要好得多。用DMD处理黄酮醇14和新型异金酮21均得到不同寻常的产物，而不是预期的环氧化物，但是，假定在反应过程中形成了环氧化物。
• 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.

表征谱图