3-(3-Chlorophenyl)-3-hydroxybutan-2-one | 936231-76-4

• 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: 3-(3-Chlorophenyl)-3-hydroxybutan-2-one
• CAS: 936231-76-4
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: GPBVTYOUBQWKAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  3-(3-Chlorophenyl)-3-hydroxybutan-2-one 在 lithium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-(3-chloro-phenyl)-5-methyl-4-oxo-4,5-dihydro-furan-2-carboxylic acid
  参考文献：
  名称：

  Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b

  摘要：

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.

  DOI：

  10.1021/jm070022x
• 作为产物：
  描述：

  3-氯苯乙酮 在 甲醇 、 正丁基锂 、 mercury(II) perchlorate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 3-(3-Chlorophenyl)-3-hydroxybutan-2-one
  参考文献：
  名称：

  Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b

  摘要：

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.

  DOI：

  10.1021/jm070022x

文献信息

• Rhodium-catalyzed addition of aryl boronic acids to 1,2-diketones and 1,2-ketoesters
  作者：Gregory R. Ganci、John D. Chisholm

  DOI：10.1016/j.tetlet.2007.09.137

  日期：2007.11

  dicyclohexylphenylphosphine provides a useful catalyst system for the addition of boronic acids to 1,2-diketones and 1,2-ketoesters. The best yields were obtained when the transformation was performed in DME/H2O at 80 °C with 4 equiv of the boronic acid. The results discussed herein extend the scope of the addition of arylboronic acids to highly activated diketones and ketoesters. The products of the reaction

  在二环己基苯基膦的存在下，金属络合物Rh（acac）（CO）2提供了有用的催化剂体系，用于将硼酸加成到1,2-二酮和1,2-酮酸酯中。当在80°C的DME / H 2 O中加入4当量的硼酸进行转化时，可获得最佳的收率。本文讨论的结果扩展了将芳基硼酸添加到高度活化的二酮和酮酸酯的范围。该反应的产物可用于合成在酯或酮之后含氧的天然产物。
• Analogues of Acifran:  Agonists of the High and Low Affinity Niacin Receptors, GPR109a and GPR109b
  作者：Jae-Kyu Jung、Benjamin R. Johnson、Tracy Duong、Marc Decaire、Jane Uy、Tawfik Gharbaoui、P. Douglas Boatman、Carleton R. Sage、Ruoping Chen、Jeremy G. Richman、Daniel T. Connolly、Graeme Semple

  DOI：10.1021/jm070022x

  日期：2007.4.1

  Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.