(4-bromophenyl)-(3-hydroxyphenyl)methanone | 62810-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-bromophenyl)-(3-hydroxyphenyl)methanone
• 英文别名: (4-Bromophenyl)(3-hydroxyphenyl)methanone
• CAS: 62810-46-2
• 化学式: C₁₃H₉BrO₂
• 分子量: 277.117
• InChiKey: XAZIYKAENTYLMA-UHFFFAOYSA-N

物化性质

• 熔点：
  170°C
• 沸点：
  423.1±25.0 °C(Predicted)
• 密度：
  1.521±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-bromophenyl)-(3-hydroxyphenyl)methanone 在 四(三苯基膦)钯 、 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 N-cyclopropyl-4'-{3-[2-(2-hydroxyethoxy)ethoxy]benzoyl}-6-methyl-[1,1'-biphenyl]-3-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of N-cyclopropylbenzamide-benzophenone hybrids as novel and selective p38 mitogen activated protein kinase (MAPK) inhibitors

  摘要：

  A series of hybrid molecules consisting of benzophenones and N-cyclopropyl-3-methylbenzamides were synthesized and biologically evaluated as novel p38 mitogen activated protein kinase (MAPK) inhibitors. In particular, we found that compound 10g displayed potent p38 alpha MAPK inhibitory activity (IC50 = 0.027 mu M), high kinase selectivity, and significant anti-inflammatory activity in THP-1 monocyte cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.036
• 作为产物：
  描述：

  (3-methoxyphenyl)magnesium bromide 在 aluminum (III) chloride 、 三丁基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.37h， 生成 (4-bromophenyl)-(3-hydroxyphenyl)methanone
  参考文献：
  名称：

  Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113930

文献信息

• Tandem Catalysis: Access to Ketones from Aldehydes and Arylboronic Acidsvia Rhodium-Catalyzed Addition/Oxidation
  作者：Guilhem Mora、Sylvain Darses、Jean-Pierre Genet

  DOI：10.1002/adsc.200600530

  日期：2007.5.7

  cross-coupling reactions of aromatic aldehydes with arylboronic acids afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst, acetone and a base. This new reaction, involving a formal aldehyde CH bond activation, is believed to proceed via a tandem process involving addition of the organometallic species to the aldehyde followed by oxidation by β-hydride transfer.

  芳族醛与芳基硼酸的直接交叉偶联反应在铑催化剂，丙酮和碱的存在下，在温和的条件下，以高收率和高产率提供了酮。据信该涉及正式醛CH键活化的新反应通过串联过程进行，该串联过程包括将有机金属物质加至醛中，然后通过β-氢化物转移进行氧化。
• Astoin; Lepage; Fromantin, European Journal of Medicinal Chemistry, 1980, vol. 15, # 5, p. 457 - 462
  作者：Astoin、Lepage、Fromantin

  DOI：——

  日期：——
• DD125658
  申请人：——

  公开号：——

  公开（公告）日：——
• ASTOIN J.; LEPAGE F.; FROMANTIN J.-P.; POISSON M., EUR. J. MED. CHEM.-CHIM. THER., 1980, 15, NO 5, 457-462
  作者：ASTOIN J.、 LEPAGE F.、 FROMANTIN J.-P.、 POISSON M.

  DOI：——

  日期：——
• Synthesis and biological evaluation of N-cyclopropylbenzamide-benzophenone hybrids as novel and selective p38 mitogen activated protein kinase (MAPK) inhibitors
  作者：Jinyuk Heo、Hanbo Shin、Jun Lee、Taelim Kim、Kyung-Soo Inn、Nam-Jung Kim

  DOI：10.1016/j.bmcl.2015.06.036

  日期：2015.9

  A series of hybrid molecules consisting of benzophenones and N-cyclopropyl-3-methylbenzamides were synthesized and biologically evaluated as novel p38 mitogen activated protein kinase (MAPK) inhibitors. In particular, we found that compound 10g displayed potent p38 alpha MAPK inhibitory activity (IC50 = 0.027 mu M), high kinase selectivity, and significant anti-inflammatory activity in THP-1 monocyte cells. (C) 2015 Elsevier Ltd. All rights reserved.