1-(3,4-dimethoxyphenyl)-3-(2-hydroxyphenyl)propan-1-one | 120645-73-0

• 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: 1-(3,4-dimethoxyphenyl)-3-(2-hydroxyphenyl)propan-1-one
• 英文别名: 3-(2-hydroxyphenyl)-1-(3,4-dimethoxyphenyl)propan-1-one；1-(3,4-dimethoxy-phenyl)-3-(2-hydroxy-phenyl)-propan-1-one；1-(3,4-Dimethoxy-phenyl)-3-(2-hydroxy-phenyl)-propan-1-on
• CAS: 120645-73-0
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: SAKNDRHTKYWELM-UHFFFAOYSA-N

物化性质

• 熔点：
  125-125.5 °C
• 沸点：
  471.1±40.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-3-(2-hydroxyphenyl)propan-1-one 在 potassium carbonate 、 对甲苯磺酰肼 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到3',4'-Dimethoxy-flavan
  参考文献：
  名称：

  Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: synthesis of 2-arylchromans

  摘要：

  Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.027
• 作为产物：
  描述：

  (2E)-3-(3,4-二甲氧基苯基)-1-(2-羟基苯基)-2-丙烯-1-酮 在 sodium tetrahydroborate 、 chloroauric acid 、 水 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 24.0h， 生成 1-(3,4-dimethoxyphenyl)-3-(2-hydroxyphenyl)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

• AMINOAMIDES AS OREXIN ANTAGONISTS
  申请人：Gobbi Luca

  公开号：US20080221166A1

  公开（公告）日：2008-09-11

  The present invention relates to compounds of formula I wherein Ar 1 , Ar 2 , Ar 3 , n, and R 1 to R 8 are as defined herein and to pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixtures thereof. These compounds are orexin receptor antagonists and may be useful in the treatment of disorders, in which orexin pathways are involved, like sleep disorders.

  本发明涉及具有以下结构的化合物（I）其中Ar1，Ar2，Ar3，n和R1至R8的定义如本文所述，并且涉及其药用适宜的酸加盐、光学纯对映体、混合物或二对映异构体。这些化合物是促进睡眠的受体拮抗剂，可能在涉及促进睡眠途径的疾病治疗中有用，如睡眠障碍。
• Aminoamides as orexin antagonists
  申请人：Hoffmann-La Roche Inc.

  公开号：US07829563B2

  公开（公告）日：2010-11-09

  The present invention relates to compounds of formula I wherein Ar1, Ar2, Ar3, n, and R1 to R8 are as defined herein and to pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixtures thereof. These compounds are orexin receptor antagonists and may be useful in the treatment of disorders, in which orexin pathways are involved, like sleep disorders.

  本发明涉及式I的化合物，其中Ar1、Ar2、Ar3、n和R1至R8的定义如本文所述，并且与药学上适用的酸盐、光学纯对映体、外消旋体或二对映异构体混合物有关。这些化合物是促进睡眠的促进剂，并且在涉及促进睡眠的疾病治疗中可能有用。
• Concise Synthesis of Dihydrochalcones via Palladium-Catalyzed Coupling of Aryl Halides and 1-Aryl-2-propen-1-ols
  作者：Anne Briot、Corinne Baehr、Raymond Brouillard、Alain Wagner、Charles Mioskowski

  DOI：10.1021/jo034936c

  日期：2004.2.1

  An expedient route to substituted dihydrochalcones is reported. The key step is a palladium-assisted arylation of 1-aryl-2-propen-1-ols. This two-step/one-purification process allows the synthesis of a wide range of compounds with original substitution patterns, including polyphenolic derivatives.
• Aulin-Erdtman et al., Svensk Papperstidn. 50<1947> Haegglund-Festschr. S.81,85
  作者：Aulin-Erdtman et al.

  DOI：——

  日期：——
• US7829563B2
  申请人：——

  公开号：US7829563B2

  公开（公告）日：2010-11-09