ethyl 7-bromooxoheptanoate | 107871-17-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 7-bromooxoheptanoate
• 英文别名: ethyl 7-bromo-2-oxoheptenoate；Ethyl 7-bromo-2-oxoheptanoate
• CAS: 107871-17-0
• 化学式: C₉H₁₅BrO₃
• 分子量: 251.12
• InChiKey: GPKZKVOWHKSXED-UHFFFAOYSA-N

物化性质

• 沸点：
  297.5±23.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  ethyl 7-bromooxoheptanoate 在 氨 、 氢溴酸 、 sodium 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 西司他丁
  参考文献：
  名称：

  Inhibition of the mammalian .beta.-lactamase renal dipeptidase (dehydropeptidase-I) by Z-2-(acylamino)-3-substituted-propenoic acids

  摘要：

  The title enzyme deactivates the potent carbapenem antibiotic imipenem in the kidney, producing low antibiotic levels in the urinary tract. A series of (Z)-2-(acylamino)-3-substituted-propenoic acids (3) are specific, competitive inhibitors of the enzyme capable of increasing the urinary concentration of imipenem in vivo. Many of the compounds were prepared in one step from an alpha-keto acid and a primary amide. The optimum R2 groups are 2,2-dimethyl, -dichloro, and -dibromocyclopropyl. With R2 = 2,2-dimethylcyclopropyl (DMCP), a wide variety of R3 groups including alkyl, oxa- and thiaalkyl, and alkyl groups containing acidic, basic, and neutral substituents give effective inhibitors with Ki values of 0.02-1 microM and a range of pharmacokinetic properties. By resolution of enantiomers and X-ray crystallography, the enzyme-inhibitory activity of the DMCP group was found to reside with the 1S isomer. The cysteinyl compound 176 (cilastatin, MK-0791) has the desired pharmacological properties and has been chosen for combination with imipenem.

  DOI：

  10.1021/jm00389a018
• 作为产物：
  描述：

  Ethyl 2-(5-bromopentyl)-1,3-dithiane-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙腈 为溶剂， 反应 0.25h， 生成 ethyl 7-bromooxoheptanoate
  参考文献：
  名称：

  Inhibition of the mammalian .beta.-lactamase renal dipeptidase (dehydropeptidase-I) by Z-2-(acylamino)-3-substituted-propenoic acids

  摘要：

  The title enzyme deactivates the potent carbapenem antibiotic imipenem in the kidney, producing low antibiotic levels in the urinary tract. A series of (Z)-2-(acylamino)-3-substituted-propenoic acids (3) are specific, competitive inhibitors of the enzyme capable of increasing the urinary concentration of imipenem in vivo. Many of the compounds were prepared in one step from an alpha-keto acid and a primary amide. The optimum R2 groups are 2,2-dimethyl, -dichloro, and -dibromocyclopropyl. With R2 = 2,2-dimethylcyclopropyl (DMCP), a wide variety of R3 groups including alkyl, oxa- and thiaalkyl, and alkyl groups containing acidic, basic, and neutral substituents give effective inhibitors with Ki values of 0.02-1 microM and a range of pharmacokinetic properties. By resolution of enantiomers and X-ray crystallography, the enzyme-inhibitory activity of the DMCP group was found to reside with the 1S isomer. The cysteinyl compound 176 (cilastatin, MK-0791) has the desired pharmacological properties and has been chosen for combination with imipenem.

  DOI：

  10.1021/jm00389a018

文献信息

• 一种西司他丁钠的制备方法
  申请人：山东新时代药业有限公司

  公开号：CN102702051B

  公开（公告）日：2016-04-13

  本发明属于药物合成领域，提供了一种西司他丁钠的制备方法，该方法包括：以7-卤氧代庚酸烷基酯与(s)-2，2-二甲基环丙烷甲酰胺为原料，经缩合、碱性水解、硫醚化后，再将硫醚化液调节pH值，通过非极性溶剂洗涤、异构化、中性大孔吸附树脂纯化、成盐等步骤得西司他丁钠固体。本发明减少了杂质的生成，提高了异构化过程的效率，制备工艺简化，有效地提高了西司他丁钠的收率和纯度。
• 一种西司他丁钠中间体的制备方法
  申请人：鲁南制药集团股份有限公司

  公开号：CN110845354B

  公开（公告）日：2020-08-25

  本发明属于医药技术领域，具体提供了一种西司他丁钠中间体的制备方法。包括以下步骤：以7‑X‑2‑氧代庚酸乙酯与(s)‑2，2‑二甲基环丙烷甲酰胺为原料，依次在催化剂、浓盐酸和氯化氢气体的作用下，经过：“一锅煮”方法简便地制得(Z)‑7‑X‑2((2s)‑2，2‑二甲基环丙烷甲酰胺基)‑2‑庚烯酸粗品，再经过重结晶得到(Z)‑7‑X‑2((2s)‑2，2‑二甲基环丙烷甲酰胺基)‑2‑庚烯酸精制品。本发明合成路线简短、操作简单、所得产品纯度较高，适合工业化生产。
• METHOD FOR PURIFYING PYRUVIC ACID COMPOUNDS
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0937703A1

  公开（公告）日：1999-08-25

  The present invention is directed to a method for purifying pyruvic acid compounds, which method comprises reacting a pyruvic acid compound of general formula (I): wherein R1 is an optionally substituted lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, and R2 is a lower alkyl group, with a bisulfite of general formula (II):         MHSO3     (II) wherein M is NH4 or an alkali metal, to give a bisulfite adduct of the pyruvic acid compound and then decomposing the adduct with an acid. According to the present invention, pyruvic acid compounds can be purified by simple and easy procedures without using purification techniques such as distillation or column chromatography, and the above method is advantageous as a process for the production on an industrial scale.

  本发明涉及一种纯化丙酮酸化合物的方法，该方法包括使通式(I)的丙酮酸化合物反应： 其中 R1 是任选取代的低级烷基、低级烯基、低级炔基、环烷基、芳基或杂环基，R2 是低级烷基，与通式（II）的亚硫酸氢盐反应： MHSO3 (II) 其中 M 为 NH4 或碱金属，以得到丙酮酸化合物的亚硫酸氢盐加合物，然后用酸分解该加合物。根据本发明，丙酮酸化合物可以通过简单易行的程序进行纯化，而无需使用蒸馏或柱层析等纯化技术，上述方法作为一种工业规模的生产工艺是非常有利的。
• INTERMEDIATE OF CILASTATIN AND PREPARATION METHOD THEREOF
  申请人：Zhejiang Hisoar Pharmaceutical Co., Ltd

  公开号：EP2394979B1

  公开（公告）日：2014-11-05
• Antibacterial composition of thienamycin type compound and a dipeptidase inhibitor
  申请人：Merck & Co., Inc.

  公开号：EP0048025B1

  公开（公告）日：1986-01-15