(S)-3-(3-溴苯基)-4-(4-氯苯基)丁-2-酮 | 1002752-54-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (S)-3-(3-溴苯基)-4-(4-氯苯基)丁-2-酮
• 英文名称: (S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-one
• 英文别名: (3S)-3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-one
• CAS: 1002752-54-6
• 化学式: C₁₆H₁₄BrClO
• 分子量: 337.644
• InChiKey: UXWQKWNHXQZIND-MRXNPFEDSA-N

物化性质

• 沸点：
  388.0±32.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-(3-溴苯基)-4-(4-氯苯基)丁-2-酮 以92的产率得到(2R,3R,4S,5R)-2-(acetoxymethyl)-5-(4-azido-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  Tetrahedron 2007, 63, 12845-12852

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-(3-溴苯基)-3-(4-氯苯基)丙酸 以90的产率得到(S)-3-(3-溴苯基)-4-(4-氯苯基)丁-2-酮
  参考文献：
  名称：

  Tetrahedron 2007, 63, 12845-12852

  摘要：

  DOI：

文献信息

• Catalytic, Enantioselective Synthesis of Taranabant, a Novel, Acyclic Cannabinoid-1 Receptor Inverse Agonist for the Treatment of Obesity
  作者：Cheng-yi Chen、Lisa F. Frey、Scott Shultz、Debra J. Wallace、Karen Marcantonio、Joeseph F. Payack、Enrique Vazquez、Shawn A. Springfield、George Zhou、Ping Liu、Gerard R. Kieczykowski、Alex M. Chen、Brian D. Phenix、Utpal Singh、Jeff Strine、Brianne Izzo、Shane W. Krska

  DOI：10.1021/op700026n

  日期：2007.5.1

  Chiral amide 1 ( MK- 0364, taranabant) is a potent, selective, and orally bioavailable cannabinoid-1 receptor ( CB-1R) inverse agonist indicated for the treatment of obesity. An asymmetric synthesis featuring a dynamic kinetic resolution via hydrogenation for the preparation of the bromo alcohol 5 is disclosed. Conversion of the alcohol intermediate to the chiral amide 1 is accomplished in good overall yield.
• Convenient total synthesis of taranabant (MK-0364), a novel cannabinoid-1 receptor inverse agonist as an anti-obesity agent
  作者：Min-ah Kim、Jong Yup Kim、Kwang-Seop Song、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.tet.2007.10.056

  日期：2007.12

  Being obese has various health problems that are related to type 2 diabetes mellitus, cardiovascular disease, hypertension, hyperlipidemia, and fibrinolytic abnormalities. Merck's taranabant (MK-0364), a CB I R inverse agonist, is currently in Phase 3 clinical trials, and is being actively pursued by Merck toward obesity market. Merck intends to file for FDA approval of taranabant in 2008. In order to overcome practical difficulty involved in lab-scale preparation of taranabant with a dynamic kinetic resolution procedure developed by Merck's process group, we developed a 'user-friendly' method to install stereogenic centers by adopting Evans asymmetry chemistry. This method allowed us to prepare readily sub-gram scale of the target compound in a convenient way. (c) 2007 Elsevier Ltd. All rights reserved.