(S)-2-(3-溴苯基)-3-(4-氯苯基)丙酸 | 1002752-55-7

• 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)-2-(3-溴苯基)-3-(4-氯苯基)丙酸
• 英文名称: (S)-2-(3-bromophenyl)-3-(4-chlorophenyl)propanoic acid
• 英文别名: (S)-2-(3-bromophenyl)-3-(4-chlorophenyl)propionic acid；(S)-2-(3-Bromophenyl)-3-(4-chlorophenyl)propanoic acid；(2S)-2-(3-bromophenyl)-3-(4-chlorophenyl)propanoic acid
• CAS: 1002752-55-7
• 化学式: C₁₅H₁₂BrClO₂
• 分子量: 339.616
• InChiKey: HMACGKZYWDFEKR-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  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：
• 作为产物：
  描述：

  (S)-2-(3-bromophenyl)-3-(4-chlorophenyl)-N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以70%的产率得到(S)-2-(3-溴苯基)-3-(4-氯苯基)丙酸
  参考文献：
  名称：

  Design, chemical synthesis, and biological evaluation of novel triazolyl analogues of taranabant (MK-0364), a cannabinoid-1 receptor inverse agonist

  摘要：

  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 CB1R 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 increase solubility and potency of taranabant, or even possibly improve safety, novel triazole analogues of taranabant have been designed and synthesized. We introduced a pivotal asymmetric center via the Evans chiral auxiliary methodology and set up 1,2,4-triazole via substitution of alpha-bromoketone. Subsequently, diastereoselective reduction was accomplished to install adjacent essential asymmetric center. This method allowed us to prepare readily sub-gram scale of the target compounds in a convenient way. The synthesized analogues were subjected to biological evaluation involving cannabinoid CB1 receptor binding affinity. While the parent taranabant bears highly potent binding affinity to cannabinoid CB1 receptor, neither of the analog structures improved CB1 receptor binding affinities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.057

文献信息

• Enantioselective iridium-catalyzed hydrogenation of α-arylcinnamic acids and synthesis of (S)-equol
  作者：Shuang Yang、Shou-Fei Zhu、Can-Ming Zhang、Song Song、Yan-Bo Yu、Shen Li、Qi-Lin Zhou

  DOI：10.1016/j.tet.2012.03.118

  日期：2012.7

  By using iridium catalyst based on chiral spiro phosphine-oxazoline ligands, the hydrogenation of alpha-arylcinnamic acids was accomplished under ambient pressure and low catalyst loading (as low as 0.01 mol %), providing useful 2,3-diarylpropionic acids in high yields with excellent enantioselectivities (up to 99% ee). A catalytic enantioselective synthesis of (S)-equol with the present hydrogenation reaction as a key step was accomplished starting from commercially available starting materials in six steps with 48.4% overall yield. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.
• Design, chemical synthesis, and biological evaluation of novel triazolyl analogues of taranabant (MK-0364), a cannabinoid-1 receptor inverse agonist
  作者：Min-ah Kim、Hoseop Yun、HyunJung Kwak、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.tet.2008.09.057

  日期：2008.11

  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 CB1R 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 increase solubility and potency of taranabant, or even possibly improve safety, novel triazole analogues of taranabant have been designed and synthesized. We introduced a pivotal asymmetric center via the Evans chiral auxiliary methodology and set up 1,2,4-triazole via substitution of alpha-bromoketone. Subsequently, diastereoselective reduction was accomplished to install adjacent essential asymmetric center. This method allowed us to prepare readily sub-gram scale of the target compounds in a convenient way. The synthesized analogues were subjected to biological evaluation involving cannabinoid CB1 receptor binding affinity. While the parent taranabant bears highly potent binding affinity to cannabinoid CB1 receptor, neither of the analog structures improved CB1 receptor binding affinities. (C) 2008 Elsevier Ltd. All rights reserved.
• Tetrahedron 2007, 63, 12845-12852
  作者：

  DOI：——

  日期：——