(2R,3S)-2,3-dimethyl-4-oxo-4-phenylbutyric acid | 946007-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-2,3-dimethyl-4-oxo-4-phenylbutyric acid
• 英文别名: (2R,3S)-2,3-dimethyl-4-oxo-4-phenylbutanoic acid
• CAS: 946007-86-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: SEHSCBSQNGYKBH-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  三甲基硅烷化重氮甲烷 、 (2R,3S)-2,3-dimethyl-4-oxo-4-phenylbutyric acid 以 甲醇 、 乙醚 、 苯 为溶剂， 生成 methyl (2R,3S)-2,3-dimethyl-4-oxo-4-phenylbutanoate
  参考文献：
  名称：

  Ligand differentiated complementary Rh-catalyst systems for the enantioselective desymmetrization of meso-cyclic anhydrides

  摘要：

  Two distinct systems for the rhodium-catalyzed enantioselective desymmetrization of meso-cyclic anhydrides have been developed. Each system has been optimized and are compatible with the use of in situ prepared organozinc reagents. Rhodium/PHOX species efficiently catalyze the addition of alkyi nucleophiles to glutaric anhydrides, while system is effective in the enantioselective arylation of succinic and glutaric anhydrides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.075
• 作为产物：
  描述：

  溴苯 、 meso-2,3-dimethylsuccinic anhydride 在 正丁基锂 、 zinc trifluoromethanesulfonate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (3AR,8AR)-(-)-(2,2-二甲基-4,4,8,8-四苯基-四氢-[1,3]二氧并[4,5-E][1,3,2]二氧磷-6-YL)二甲胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (+/-)-erythro-4-oxo-2.3-dimethyl-4-phenyl-butyric acid 、 (2R,3S)-2,3-dimethyl-4-oxo-4-phenylbutyric acid
  参考文献：
  名称：

  Ligand differentiated complementary Rh-catalyst systems for the enantioselective desymmetrization of meso-cyclic anhydrides

  摘要：

  Two distinct systems for the rhodium-catalyzed enantioselective desymmetrization of meso-cyclic anhydrides have been developed. Each system has been optimized and are compatible with the use of in situ prepared organozinc reagents. Rhodium/PHOX species efficiently catalyze the addition of alkyi nucleophiles to glutaric anhydrides, while system is effective in the enantioselective arylation of succinic and glutaric anhydrides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.075

文献信息

• THERAPEUTIC AGENT FOR DIABETES
  申请人：Japan Tobacco Inc.

  公开号：EP0885869A1

  公开（公告）日：1998-12-23

  A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4 and R5 are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6 is a hydrogen atom or an amino-protecting group; R1 is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2 is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3 is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.

  用于治疗糖尿病的疗法剂，包括公式[I]的化合物 其中 X是公式的组 其中R4和R5相同或不同，每个都是氢原子，可选地取代的具有1至5个碳原子的烷基等等，R6是氢原子或氨基保护基团；R1是具有1至5个碳原子的可选取代烷基，具有2至6个碳原子的可选取代烯基等等，R2是氢原子，具有1至5个碳原子的可选取代烷基等等，R2'是氢原子，R3是具有1至5个碳原子的可选取代烷基等等，其前药，药用可接受盐，水合物和溶剂化物。 本发明的化合物在血糖升高状态下表现出优越的降血糖作用，但在正常范围或低血糖状态下不影响血糖，这意味着它没有低血糖等严重副作用。因此，本发明的化合物作为治疗糖尿病的药物很有用，也用作预防糖尿病慢性并发症。
• A Palladium-Catalyzed Enantioselective Alkylative Desymmetrization of <i>m</i><i>eso</i>-Succinic Anhydrides
  作者：Eric A. Bercot、Tomislav Rovis

  DOI：10.1021/ja046528b

  日期：2004.8.1

  Monoalkylation of cyclic anhydrides provides an opportunity to couple a carbon-carbon bond-forming event with the control of backbone stereochemistry. We have developed a palladium-JOSIPHOS catalyst system that desymmetrizes meso-succinic anhydrides using organozinc reagents as nucleophiles, and have found that, in many cases, this reaction proceeds at ambient temperature.

  环状酸酐的单烷基化提供了将碳-碳键形成事件与骨架立体化学控制相结合的机会。我们开发了一种钯-JOSIPHOS 催化剂体系，该体系使用有机锌试剂作为亲核试剂使内消旋琥珀酸酐去对称化，并发现在许多情况下，该反应在环境温度下进行。
• A Concise Synthesis of Eupomatilones 4, 6, and 7 by Rhodium-Catalyzed Enantioselective Desymmetrization of Cyclicmeso Anhydrides with Organozinc Reagents Generated In Situ
  作者：Jeffrey B. Johnson、Eric A. Bercot、Catherine M. Williams、Tomislav Rovis

  DOI：10.1002/anie.200700816

  日期：2007.6.11
• Ligand differentiated complementary Rh-catalyst systems for the enantioselective desymmetrization of meso-cyclic anhydrides
  作者：Jeffrey B. Johnson、Matthew J. Cook、Tomislav Rovis

  DOI：10.1016/j.tet.2008.10.075

  日期：2009.4

  Two distinct systems for the rhodium-catalyzed enantioselective desymmetrization of meso-cyclic anhydrides have been developed. Each system has been optimized and are compatible with the use of in situ prepared organozinc reagents. Rhodium/PHOX species efficiently catalyze the addition of alkyi nucleophiles to glutaric anhydrides, while system is effective in the enantioselective arylation of succinic and glutaric anhydrides. (C) 2008 Elsevier Ltd. All rights reserved.