1-(3-溴苯基)-3-(2-羟基苯基)丙烷-1,3-二酮 | 109899-86-7

• 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
• 中文名称: 1-(3-溴苯基)-3-(2-羟基苯基)丙烷-1,3-二酮
• 英文名称: 1-(3-bromophenyl)-3-(2-hydroxyphenyl)propane-1,3-dione
• 英文别名: 1,3-Propanedione, 1-(3-bromophenyl)-3-(2-hydroxyphenyl)-
• CAS: 109899-86-7
• 化学式: C₁₅H₁₁BrO₃
• 分子量: 319.155
• InChiKey: YFQJPKDFWNKLHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-溴苯基)-3-(2-羟基苯基)丙烷-1,3-二酮 在 Amberlist 15 resin 作用下， 以 异丙醇 为溶剂， 反应 19.5h， 以67%的产率得到2-(3-bromophenyl)-4H-chromen-4-one
  参考文献：
  名称：

  A Facile Preparation of Flavones Using Nonaqueous Cation-Exchange Resin

  摘要：

  黄酮是通过使用无水阳离子交换树脂从1-(2-羟基苯基)-3-苯基-1,3-丙二酮制备的，几乎具有定量的产率。在几种反应介质中，异丙醇给出了最佳结果。还从相应的二酮合成了八种取代的黄酮，并且产率令人满意。

  DOI：

  10.1246/bcsj.60.1919
• 作为产物：
  描述：

  3-Bromo-benzoic acid 2-acetyl-phenyl ester 在 氢氧化钾 作用下， 以 吡啶 为溶剂， 生成 1-(3-溴苯基)-3-(2-羟基苯基)丙烷-1,3-二酮
  参考文献：
  名称：

  Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor

  摘要：

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00343-0

文献信息

• Rh(III)‐Catalyzed Aldehydic C−H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides
  作者：Guo‐Dong Xu、Kenneth L. Huang、Zhi‐Zhen Huang

  DOI：10.1002/adsc.201900276

  日期：2019.7.11

  A novel aldehydic C−H functionalization reaction between salicylaldehydes and sulfoxonium ylides has been developed under rhodium(III) catalysis, affording coupling products in moderate to good yields. A plausible mechanism involving aldehydic C(sp2)−H activation by rhodium(III) and rhodium(III) catalyzed carbene insertion is also proposed. It was also found that the aldehydic C−H functionalization

  在铑（III）催化下，开发了水杨醛与亚磺酰之间的新型醛C-H官能化反应，可提供中等至良好收率的偶联产物。还提出了一种可能的机理，该机理涉及通过铑（III）和铑（III）催化的卡宾插入而使醛类的C（sp 2）-H活化。还发现醛化的CH功能化然后脱水环化能够在一锅中产生类黄酮。
• A Facile Preparation of Flavones Using Nonaqueous Cation-Exchange Resin
  作者：Yukio Hoshino、Noboru Takeno

  DOI：10.1246/bcsj.60.1919

  日期：1987.5

  Flavone was prepared from 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione by using nonaqueous cationexchange resin in a nearly quantitative yield. Of several reaction media, isopropyl alcohol gave the best result. Eight substituted flavones were also synthesized from the corresponding diketones in satisfactory yields.

  黄酮是通过使用无水阳离子交换树脂从1-(2-羟基苯基)-3-苯基-1,3-丙二酮制备的，几乎具有定量的产率。在几种反应介质中，异丙醇给出了最佳结果。还从相应的二酮合成了八种取代的黄酮，并且产率令人满意。
• Bowden, Keith; Chehel-Amiran, Mohsen, Journal of the Chemical Society. Perkin transactions II, 1986, p. 2039 - 2044
  作者：Bowden, Keith、Chehel-Amiran, Mohsen

  DOI：——

  日期：——
• HOSHINO YUKIO; TAKENO NOBORU, BULL. CHEM. SOC. JAP., 60,(1987) N 5, 1919-1920
  作者：HOSHINO YUKIO、 TAKENO NOBORU

  DOI：——

  日期：——
• Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor
  作者：Mariel Marde、Juan Zinczuk、María I. Colombo、Cristina Wasowski、Haydee Viola、Claudia Wolfman、Jorge H. Medina、Edmundo A. Rúveda、Alejandro C. Paladini

  DOI：10.1016/s0960-894x(97)00343-0

  日期：1997.8

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.