3-(5-chloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)-propan-1-one | 1413850-07-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(5-chloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)-propan-1-one
• 英文别名: 3-(5-Chloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)-propan-1-one；3-(5-chloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)propan-1-one
• CAS: 1413850-07-3
• 化学式: C₁₆H₁₅ClO₃
• 分子量: 290.746
• InChiKey: GEEQFLHNUHGGDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  6-Chloro-2-(4-methoxy-phenyl)-2H-chromene 在 chloroauric acid 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以87%的产率得到3-(5-chloro-2-hydroxyphenyl)-1-(4-methoxyphenyl)-propan-1-one
  参考文献：
  名称：

  An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4

  摘要：

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.117

文献信息

• Reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans into 2-hydroxydihydrochalcones and flav-2-enes
  作者：Dmitry V. Osipov、Maxim R. Demidov、Vitaly А. Osyanin、Yuri N. Klimochkin

  DOI：10.1007/s10593-021-03039-6

  日期：2021.12

  4-diaryl-substituted 4H-chromenes by the formal [4+1] cycloaddition reaction of o-quinone methides and pyridinium ylides followed by reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid or samarium and trimethylchlorosilane in 1,4-dioxane. The reduction of 3-unsubstituted 2-aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid leads mainly to 2-hydroxydihydrochalcones

  提出了通过邻醌甲基化物和吡啶鎓叶立德的形式 [4+1] 环加成反应然后还原重排合成 2-芳基和 2,4-二芳基取代的 4 H-色烯的两步程序。 2-芳酰基-2,3-二氢苯并呋喃通过乙酸中的锌或钐和 1,4-二恶烷中的三甲基氯硅烷的作用。通过乙酸中锌的作用还原 3-未取代的 2-芳酰基-2,3-二氢苯并呋喃主要产生 2-羟基二氢查耳酮。
• An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
  作者：Gourhari Maiti、Utpal Kayal、Rajiv Karmakar、Rudraksha N. Bhattacharya

  DOI：10.1016/j.tetlet.2012.08.117

  日期：2012.11

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.