rac-trans-3,4-bis(methoxycarbonyl)hexanedioic acid | 1523530-45-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: rac-trans-3,4-bis(methoxycarbonyl)hexanedioic acid
• 英文别名: threo-3,4-bis(methoxycarbonyl)hexanedioic acid；(2r,3r)-Rel-1,2,3,4-butanetetracarboxylic acid, 2,3-dimethyl ester；(3S,4S)-3,4-bis(methoxycarbonyl)hexanedioic acid
• CAS: 1523530-45-1
• 化学式: C₁₀H₁₄O₈
• 分子量: 262.216
• InChiKey: FKFVPINWMGATEI-WDSKDSINSA-N

物化性质

• 沸点：
  478.1±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  rac-trans-3,4-bis(methoxycarbonyl)hexanedioic acid 在 sodium hydroxide 、 phosphate buffer solution 、 pig liver esterase(PLE) 、 sodium acetate 、 乙酸酐 作用下， 反应 1.0h， 生成 (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid
  参考文献：
  名称：

  Rosenquist, Asa; Kvarnstroem, Ingemar; Svensson, Stefan C. T., Acta Chemica Scandinavica, 1992, vol. 46, # 11, p. 1127 - 1129

  摘要：

  DOI：
• 作为产物：
  描述：

  rac-trans-4,5-bis(methoxycarbonyl)cyclohexene 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以90%的产率得到rac-trans-3,4-bis(methoxycarbonyl)hexanedioic acid
  参考文献：
  名称：

  Rosenquist, Asa; Kvarnstroem, Ingemar; Svensson, Stefan C. T., Acta Chemica Scandinavica, 1992, vol. 46, # 11, p. 1127 - 1129

  摘要：

  DOI：

文献信息

• [EN] PROCESSES AND INTERMEDIATES FOR PREPARING A MACROCYCLIC PROTEASE INHIBITOR OF HCV<br/>[FR] PROCÉDÉS ET INTERMÉDIAIRES POUR LA PRÉPARATION D'UN INHIBITEUR DE PROTÉASE MACROCYCLIQUE DU VHC
  申请人：JANSSEN PHARMACEUTICALS INC

  公开号：WO2013041655A1

  公开（公告）日：2013-03-28

  Disclosed is a process for the preparation of a cinchonidine salt of formula (IV) via an aqueous solution of a racemic 4-hydroxy-1,2-cyclopentanedicarboxylic acid, which is subjected to cyclization without removing water, by the addition of a water- miscible organic solvent to the aqueous solution and, again without removing water, adding cinchonidine to the aqueous-organic solvent solution so as to obtain the cinchonidine salt of the lactone acid. The cinchonidine salt is allowd to crystallize so as to obtain the enantiomerically purified crystalline lactone acid cinchonidine salt (IV). The enantiomerically pure salt is an intermediate in the synthesis of HCV inhibitor compound of formula (I).

  揭示了一种制备奎宁啉盐（IV式）的过程，通过将外消旋4-羟基-1,2-环戊二羧酸的水溶液进行环化，无需去除水，向水溶液中加入水亲和性有机溶剂，再次无需去除水，将奎宁啉加入水-有机溶剂溶液中，以获得内酯酸奎宁啉盐。奎宁啉盐被允许结晶，以获得对映纯化的结晶内酯酸奎宁啉盐（IV式）。对映纯盐是合成HCV抑制剂化合物（I式）的中间体。
• HEPATITIS C SERINE PROTEASE INHIBITORS AND USES THEREFOR
  申请人：Campbell David Alan

  公开号：US20090325889A1

  公开（公告）日：2009-12-31

  The present invention provides novel compounds which mimic peptides with a C-terminal penultimate proline, such compounds being useful as protease inhibitors, particularly as inhibitors of serine proteases, and more particularly as inhibitors of the NS3 serine protease from hepatitis C. The compounds find utility as antiviral agents directed at hepatitis C. The invention further provides methods of employing such inhibitors, alone or in combination with other therapeutic agents, to treat hepatitis C infection in a subject in need of such treatment.

  本发明提供了一种新型化合物，其模拟具有C-末端次末端脯氨酸的肽，这些化合物可用作蛋白酶抑制剂，特别是丝氨酸蛋白酶的抑制剂，更特别地，作为丙型肝炎NS3丝氨酸蛋白酶的抑制剂。这些化合物可用作针对丙型肝炎的抗病毒剂。本发明还提供了使用这些抑制剂的方法，单独或与其他治疗剂联合使用，用于治疗需要此类治疗的患者的丙型肝炎感染。
• Processes and Intermediates for Preparing a Macrocyclic Protease Inhibitor of HCV
  申请人：Ormerod Dominic John

  公开号：US20130005976A1

  公开（公告）日：2013-01-03

  A process for preparing [(1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, by the resolution of racemic 4-oxo-1,2-cyclopentanedicarboxylic acid (V), said process comprising: (a) reacting 4-oxo-1,2-cyclopentanedicarboxylic acid (V) with brucine or (1R,2S)-(−)-ephedrine, thus preparing the bis-brucine or bis-(1R,2S)-(−)-ephedrine salt of (V), and (b) precipitating selectively the bis-brucine or bis-(1R,2S)-(−)-ephedrine salt of (1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, while the bis-brucine or bis-(1R,2S)-(−)-ephedrine salt of [(1S,2S)-4-oxo-1,2-cyclopentanedicarboxylic acid stays in solution; (c) liberating the acid II by removal of brucine or (1R,2S)-(−)-ephedrine from the precipitated salt obtained in step (b).

  一种制备[(1R,2R)-4-氧代-1,2-环戊烷二羧酸II]的方法，通过拆分混合物中的4-氧代-1,2-环戊烷二羧酸(V)得到，该方法包括：(a)将4-氧代-1,2-环戊烷二羧酸(V)与金雀碱或(1R,2S)-(-)-麻黄碱反应，从而制备出(V)的双金雀碱或双(1R,2S)-(-)-麻黄碱盐，(b)有选择地沉淀(1R,2R)-4-氧代-1,2-环戊烷二羧酸II的双金雀碱或双(1R,2S)-(-)-麻黄碱盐，而双金雀碱或双(1R,2S)-(-)-麻黄碱盐的[(1S,2S)-4-氧代-1,2-环戊烷二羧酸]保持在溶液中；(c)通过从步骤(b)中沉淀的盐中去除金雀碱或(1R,2S)-(-)-麻黄碱来释放酸II。
• PROCESSES AND INTERMEDIATES FOR PREPARING A MACROCYCLIC PROTEASE INHIBITOR OF HCV
  申请人：Janssen Pharmaceuticals, Inc.

  公开号：EP3239129A1

  公开（公告）日：2017-11-01

  A process for preparing [(1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, by the resolution of racemic 4-oxo-1,2-cyclopentanedicarboxylic acid (V), said process comprising: (a) reacting 4-oxo-1,2-cyclopentanedicarboxylic acid (V) with brucine or (1R,2S)-(-)-ephedrine, thus preparing the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of (V), and (b) precipitating selectively the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of (1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid II, while the bis-brucine or bis-(1R,2S)-(-)-ephedrine salt of [(1S,2S)-4-oxo-1,2-cyclopentanedicarboxylic acid stays in solution; (c) liberating the acid II by removal of brucine or (1R,2S)-(-)-ephedrine from the precipitated salt obtained in step (b).

  一种通过外消旋 4-氧代-1,2-环戊烷二羧酸（V）的解析制备[(1R,2R)-4-氧代-1,2-环戊烷二羧酸 II]的工艺，所述工艺包括 (a) 将 4-氧代-1,2-环戊烷二羧酸(V)与布鲁氨酸或(1R,2S)-(-)-麻黄碱反应，从而制备 (V)的双布鲁氨酸盐或双(1R,2S)-(-)-麻黄碱盐，以及 (b) 选择性地析出(1R,2R)-4-氧代-1,2-环戊烷二羧酸 II 的双丁氨酸盐或双-(1R,2S)-(-)-麻黄碱盐，而[(1S,2S)-4-氧代-1,2-环戊烷二羧酸]的双丁氨酸盐或双-(1R,2S)-(-)-麻黄碱盐留在溶液中； (c) 从步骤(b)得到的沉淀盐中除去布鲁氨酸或(1R,2S)-(-)-麻黄碱，从而释放出酸 II。
• Boumchita, Hassane; Legraverend, Michel; Bisagni, Emile, Heterocycles, 1991, vol. 32, # 9, p. 1785 - 1792
  作者：Boumchita, Hassane、Legraverend, Michel、Bisagni, Emile

  DOI：——

  日期：——