(E)-2-[3-[3-[2-(7-氯-2-喹啉基)乙烯基]苯基]-3-氧代丙基]苯甲酸甲酯 | 149968-11-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: (E)-2-[3-[3-[2-(7-氯-2-喹啉基)乙烯基]苯基]-3-氧代丙基]苯甲酸甲酯
• 中文别名: 孟鲁司特3-氧基苯甲酸酯
• 英文名称: methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate
• 英文别名: (E)-2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-oxopropyl>benzoic acid methyl ester；2-[3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoic Acid Methyl Ester；methyl 2-[3-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-oxopropyl]benzoate
• CAS: 149968-11-6
• 化学式: C₂₈H₂₂ClNO₃
• 分子量: 455.941
• InChiKey: INXATVZSQVIIHJ-NTEUORMPSA-N

物化性质

• 熔点：
  124-126°C
• 沸点：
  659.7±55.0 °C(Predicted)
• 密度：
  1.271
• 溶解度：
  可溶于氯仿（轻微）、DMSO（轻微）、甲醇（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  室温且干燥

制备方法与用途

(E)-2-[3-(3-{2-(7-氯-2-喹啉基)乙烯基}苯基)-3-氧代丙基]苯甲酸甲酯是孟鲁斯特的一种杂质，常用于标准品和对照品的研究。

反应信息

• 作为反应物：
  描述：

  (E)-2-[3-[3-[2-(7-氯-2-喹啉基)乙烯基]苯基]-3-氧代丙基]苯甲酸甲酯 在 cerium(III) chloride 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-[2-[3(S)-[3-(7-氯-2-喹啉基)乙烯基]苯基]-3-羟基丙基]苯基-2-丙醇
  参考文献：
  名称：

  Sunil Kumar; Anjaneyulu; Hima Bindu, Asian Journal of Chemistry, 2011, vol. 23, # 10, p. 4536 - 4546

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-[2-(7-氯-2-喹啉基)乙烯基]苯甲醛 在 palladium diacetate 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 13.0h， 生成 (E)-2-[3-[3-[2-(7-氯-2-喹啉基)乙烯基]苯基]-3-氧代丙基]苯甲酸甲酯
  参考文献：
  名称：

  An efficient synthesis of LTD4 antagonist L-699,392

  摘要：

  The asymmetric synthesis of L-699,392 (1) [3-[[(1S)-[3(E)-[2-(7-chloroquinolinyl)ethenyl]phenyl]-3-(acetylphenyl)propyl]thiol-2(S)-methylpropanoic acid], a leukotriene antagonist, is accomplished in six steps starting from the monoaldehyde 2. The main framework of the molecule is formed via a Pd-catalyzed Heck reaction. The asymmetric center is introduced via the chiral reduction of the ketone 4 using optically active B-chlorodiisopinocampheylborane (10) derived directly from chloroborane and (-)-alpha-pinene. A very high asymmetric amplification is observed in which 95 % ee product can be obtained from 70% optically pure a-pinene. Reagent 17, which is prepared in situ from methylmagnesium chloride and 2 equiv of lithium hexamethyldisilazide, is used to convert the methyl ester 5 to the methyl ketone 6 in one step with essentially no impurities formed under the reaction conditions. The thio side chain is finally incorporated by the displacement of the chiral mesylate 7 with complete inversion at the chiral center. The overall yield for the sequence is 42%.

  DOI：

  10.1021/jo00066a027

文献信息

• CYSTEINYL LEUKOTRIENE ANTAGONISTS
  申请人：Rathod Rajendrasinh

  公开号：US20140155596A1

  公开（公告）日：2014-06-05

  The present invention relates to novel cysteinyl leukotriene (specifically LTD4) antagonists, mainly to quinolin, quinoxaline or benz[c]thiazole derivatives represented by the general formula (I), or the pharmaceutically acceptable salt thereof, process of preparation thereof, and to the use of the compounds in the preparation of pharmaceutical compositions for the therapeutic treatment of disorders related to cysteinyl leukotriene, in mammals, more specially in humans.

  本发明涉及新型半胱氨酸类白三烯（特别是LTD4）拮抗剂，主要是由一般式（I）所代表的喹啉、喹喔啉或苯[c]噻唑衍生物，或其药学上可接受的盐，其制备方法，以及在哺乳动物，特别是人类中，用这些化合物制备用于治疗与半胱氨酸类白三烯相关的疾病的药物组合物。
• [EN] A PROCESS FOR SYNTHESIZING DIOL (VIII)-AN INTERMEDIATE OF MONTELUKAST SODIUM<br/>[FR] PROCEDE POUR SYNTHETISER UN DIOL (VIII), INTERMEDIAIRE DU SODIUM DE MONTELUKAST
  申请人：MOREPEN LAB LTD

  公开号：WO2006021974A1

  公开（公告）日：2006-03-02

  A process comprises preparing benzaldehyde of formula I in a conventional manner, reacting the said benzaldehyde I with Grignard reagent in water miscible etheral solvent to precipitate the alcohol of formula (II) by addition of ammonium salt and water followed by isolating the alcohol thus precipitated by any known methods and then oxidizing directly under 'Swern's conditions' to get a ketone of formula m, enolizing the said ketone in presence of a mild base such as alkali metal alkoxide and then reacting it with dialkyl carbonate under conditions effective to yield a β- ketoester of formula IV, benzylating the said β-ketoester so obtained in the preceding step to form the benzoate of formula V in presence of mild inorganic base followed by decarboxylating the said benzoate to a mixture of a ketoester of formula VI and its corresponding acid of formula VIA in the presence of acidic conditions, alkylating the acid VIA present in the mixture in the preceding step to obtain ketoester of formula VI and purifying it if so desired, asymmetrically reducing the ketoester of formula VI, to a chiral alcohol of formula VII using (-) diisopinocamphenylchloroborane (-DIPC1) in presence of less than 4 times v/w aprotic solvent and optionally in presence of Lewis base with respect to the said ketoester of formula VI, treating the said chiral alcohol VII with cerium halo salt, and alkylmagnesium halide followed by isolating the title compound using hyflow supercel and ammonium chloride to get the intermediate diol of formula VIII. Atemately, the said alcohol to Heck coupling with methyl-2-iodobenzoate in presence of Lewis base, acetonitrile, and palladium acetate to yield ketoester (VI), which is converted to diol (VIII) as described herein above.

  该过程包括以传统方式制备化学式I的苯甲醛，将所述苯甲醛I与格氏试剂在水溶性醚溶剂中反应，通过加入铵盐和水使醇II沉淀，随后通过任何已知方法分离沉淀的醇，然后在“Swern条件”下直接氧化以得到化学式m的酮，使所述酮在存在弱碱（如碱金属碱）的情况下烯醇化，然后在条件下与二烷基碳酸酯反应以产生化学式IV的β-酮酯，将在前一步骤中获得的β-酮酯苄化以在温和无机碱存在下形成化学式V的苯甲酸酯，随后在酸性条件下将所述苯甲酸酯脱羧为化学式VI的酮酯和其对应酸化学式VIA的混合物，将在前一步骤中存在的酸VIA烷化以获得化学式VI的酮酯，并在必要时纯化，将化学式VI的酮酯不对称还原为手性醇化学式VII，使用(-)二异萜基氯硼烷(-DIPC1)在少于4倍体积/重量的无极性溶剂和可能在存在于所述化学式VI的酮酯相对于Lewis碱的情况下，用铈卤盐和烷基镁卤化物处理所述手性醇VII，随后使用hyflow supercel和氯化铵分离标题化合物以获得化学式VIII的中间二醇。或者，将所述醇与甲基-2-碘苯酸甲酯在Lewis碱、乙腈和乙酸钯存在下进行Heck偶联反应，得到酮酯(VI)，然后将其转化为所述化学式VIII的二醇，如上所述。
• [EN] BIARYL DIPHOSPHINE LIGANDS, INTERMEDIATES OF THE SAME AND THEIR USE IN ASYMMETRIC CATALYSIS<br/>[FR] LIGANDS BIARYLES DIPHOSPHINES, INTERMÉDIAIRES ET UTILISATION DANS LA CATALYSE ASYMÉTRIQUE
  申请人：KANATA CHEMICAL TECHNOLOGIES INC

  公开号：WO2012031358A1

  公开（公告）日：2012-03-15

  The present disclosure relates to biaryl diphosphine ligands of the formula (B), processes for the production of the ligands and the use of the ligands in metal catalysts for asymmetric synthesis. The disclosure also relates to intermediates used for the production of the biaryl diphosphine ligand. (Formula (B))

  本公开涉及公式（B）的联苯二膦配体，制备该配体的方法以及在金属催化剂中用于不对称合成的配体的使用。该公开还涉及用于生产联苯二膦配体的中间体。（公式（B））
• Homogeneous asymmetric hydrogenation catalyst
  申请人：Shimizu Hideo

  公开号：US20090203927A1

  公开（公告）日：2009-08-13

  Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.

  提供一种用于均相氢化的有用催化剂，特别是用于均相不对称氢化的催化剂，特别是不对称氢化的催化剂，该催化剂易于获得，在经济性和可操作性方面表现出色，以及一种使用该催化剂产生不饱和化合物的氢化物的方法，特别是使用高产率和光学纯度的该催化剂产生手性活性化合物。
• A convenient and economical method for the preparation of DIP-Chloridetm and its application in the asymmetric reduction of aralkyl ketones
  作者：Mangzhu Zhao、Anthony O. King、Robert D. Larsen、Thomas R. Verhoeven、Paul J. Reider

  DOI：10.1016/s0040-4039(97)00440-1

  日期：1997.4

  A convenient and economical in situ preparation of DIP-Chloridetm from NaBH4, BCl3 and α-pinene is described. Its application in the asymmetric reduction of representative aralkyl ketones is presented.

  描述了从NaBH 4，BCl 3和α-pine烯方便，经济地原位制备DIP-氯化物tm的方法。介绍了其在代表性芳烷基酮的不对称还原中的应用。