酮洛芬2-氯乙酯 | 114315-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 酮洛芬2-氯乙酯
• 英文名称: 2-chloroethyl ester of 2-(3-benzoylphenyl)propionic acid
• 英文别名: ketoprofen 2-chloroethyl ester；ketoprofen chloroethyl ester；2-chloroethyl 2-(3-benzoylphenyl)propanoate
• CAS: 114315-58-1
• 化学式: C₁₈H₁₇ClO₃
• 分子量: 316.784
• InChiKey: QDJOFGCFCRWUQE-UHFFFAOYSA-N

物化性质

• 沸点：
  454.7±30.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  酮洛芬2-氯乙酯 在 lipase OF I 作用下， 以 水 为溶剂， 反应 36.0h， 生成 右旋酮洛芬
  参考文献：
  名称：

  Enhancement of the enantioselectivity of lipase OF catalyzed hydrolysis

  摘要：

  By rational purification of lipase OF on a mercurial affinity column three fi actions were identified as responsible for the improved enantioselectivity without compromising the total activity of the crude enzyme. These three portions of lipase OF have remarkably different abilities to differentiate between the enantiomers of alpha -arylpropionic acids in the lipase catalyzed hydrolysis of the corresponding esters. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00017-9
• 作为产物：
  描述：

  ketoprofen chloride 、 2-氯乙醇 在 碳酸氢钠 作用下， 以 苯 为溶剂， 反应 4.0h， 以89%的产率得到酮洛芬2-氯乙酯
  参考文献：
  名称：

  Synthesis of Amphiphilic Conjugates Based on Silicon-Containing β-Cyclodextrin and Pharmacologically Important Acids

  摘要：

  Amphiphilic conjugates were obtained containing fragments of pharmacologically important monocarboxylic aromatic acids, which are of interest for biomedical research, have been obtained basing on 6-O-tert-butyldimethylsilyl -cyclodextrin derivative.

  DOI：

  10.1134/s1070363219050141

文献信息

• Enantioselective inhibition: strategy for improving the enantioselectivity of biocatalytic systems
  作者：Zhi Wei Guo、Charles J. Sih

  DOI：10.1021/ja00199a053

  日期：1989.8

  enantiomerically pure (R)-(+)-DCPP and (S)-(-)-DCPP. The observed inhibition pattern was that of partial noncompetitive inhibition for (R)-(+)-DCPP and that of pure noncompetitive inhibition for (S)-(-)-DCPP. Enantioselective biocatalysis in aqueous' and nonaqueousZ media is becoming increasingly important as a possible alternative method for the resolution of enantiomers. In recent years, hydrolytic enzymes such

  发现右美沙芬 (DM) 和左美沙芬 (LM) 是圆柱假丝酵母脂肪酶催化的多种 (*)-芳基丙酸酯和 (&)-(芳氧基)丙酸酯水解的有效对映选择性抑制剂。在 DM 或 LM 存在下，(&)-甲基 2-(2,4-二氯苯氧基)丙酸酯 (DCPP) 的生物催化拆分的对映选择性提高了 20 倍。已经开发了对映选择性抑制的通用模型，并且已经导出了定量表达式以显示控制对映选择性抑制的潜在参数。为了确定 DM 的作用机制，使用对映异构纯的 (R)-(+)-DCPP 和 (S)-(-)-DCPP 进行了一系列动力学抑制实验。观察到的抑制模式是 (R)-(+)-DCPP 的部分非竞争性抑制和 (S)-(-)-DCPP 的纯非竞争性抑制。水介质和非水介质中的对映选择性生物催化作为拆分对映体的一种可能的替代方法变得越来越重要。近年来，水解酶如猪肝酶、猪胰脂肪酶 Ic 和微生物脂肪酶 Ic (EC 3.1.1.3)
• A PRACTICAL ENZYMATIC METHOD FOR PREPARATION OF (<i>S</i>)-KETOPROFEN WITH A CRUDE<i>CANDIDA RUGOSA</i>LIPASE
  作者：Hui-Yuan Wu、Jian-He Xu、You-Yan Liu

  DOI：10.1081/scc-100106210

  日期：2001.1

  A simple and practical method for the preparation of (S)-Ketoprofen (2-(3-benzoylphenyl) propionic acid) has been developed through the hydrolysis of its chloroethyl ester catalyzed by a cheap and commercially available crude Candida rugosa lipase preparation under an extremely acidic condition, pH 2.5, and in the presence of Tween-80. As the reaction was carried out in a shake flask with baffles,

  开发了一种简单实用的制备（S）-酮洛芬（2-（3-苯甲酰基苯基）丙酸）氯乙酯的方法，该方法由廉价且市售的粗假丝酵母脂肪酶制剂催化，在极其苛刻的条件下进行。酸性条件，pH 2.5，并存在 Tween-80。由于反应在带挡板的摇瓶中进行，水解度从31.5%提高到42.2%。经简单分离纯化，得到(S)-酮洛芬针状结晶，ee值为95.7%。
• Process for preparing (S)-alpha-methylarylacetic acids
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：EP0227078A1

  公开（公告）日：1987-07-01

  The invention relates to a process for preparing (S)-alpha-methylarylacetic acids from mixtures, such as racemic mixtures, of (R)-and (S)-alpha-methylarylacetic acid esters by enantiospecific hydrolysis using extracellular lipases of microbial origin (EC 3.1.1.3). Preferably S-2-(6-methoxy-2-naphthyl)-alpha-methylacetic acid is prepared (S-Naproxen).

  该发明涉及一种从混合物中制备（S）-α-甲基芳基乙酸的过程，例如光学异构体混合物，通过使用微生物来源的胞外脂肪酶（EC 3.1.1.3）进行对映选择性水解。最好制备S-2-（6-甲氧基-2-萘基）-α-甲基乙酸（S-Naproxen）。
• Cross-Linked Crystals of Candida rugosa Lipase: Highly Efficient Catalysts for the Resolution of Chiral Esters
  作者：Jim J. Lalonde、Chandrika Govardhan、Nazer Khalaf、Aldo G. Martinez、Kalevi Visuri、Alexey L. Margolin

  DOI：10.1021/ja00131a006

  日期：1995.7

  To date, most enzyme-based organic syntheses have employed enzymes in the form. of a crude protein extract. The instability and expense of highly purified proteins has all but obviated their use as catalysts for enantioselective hydrolyses. Herein, we describe the use of the major hydrolase from commercial Candida rugosa lipase (CRL) in the form of a cross-linked enzyme crystal (CLEC) for the enantioselective hydrolysis of chiral racemic esters. The enantioselectivity of CRL-CLECs in the hydrolysis of many important chiral esters is vastly superior to that of the crude CRL extract. Since the CRL-CLEC is insoluble, recoverable, and 2-3 orders of magnitude more stable than the soluble protein, the CRL-CLEC is an attractive replacement for the crude enzyme preparation. The use of this catalyst in the resolution of chiral esters 1-11 and in the preparative scale (la):and multicycle resolution (2a) of important anti-inflammatory drugs is described.
• US5587318A
  申请人：——

  公开号：US5587318A

  公开（公告）日：1996-12-24