Glutaraminsaeureethylester | 56703-79-8

• 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: Glutaraminsaeureethylester
• 英文别名: Glutarsaeureethylesteramid；Ethyl 5-amino-5-oxopentanoate
• CAS: 56703-79-8
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: YIQNVBGZFQXZPD-UHFFFAOYSA-N

物化性质

• 沸点：
  319.4±25.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Glutaraminsaeureethylester 在 四氯化钛 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 以90%的产率得到戊二酸
  参考文献：
  名称：

  酰胺的轻度水解或醇解。Ti(IV) 催化伯甲酰胺转化为羧酸或酯

  摘要：

  伯酰胺（例如，1a 或 6-13）或 O-甲基异羟肟酸酯（1b 和 1c）与催化量的 TiCl4 和一当量的 HCl 水溶液反应，这些化合物以良好的产率转化为碳...

  DOI：

  10.1139/v94-022
• 作为产物：
  描述：

  戊二酸单乙酯酰氯 在 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 Glutaraminsaeureethylester
  参考文献：
  名称：

  酰胺的轻度水解或醇解。Ti(IV) 催化伯甲酰胺转化为羧酸或酯

  摘要：

  伯酰胺（例如，1a 或 6-13）或 O-甲基异羟肟酸酯（1b 和 1c）与催化量的 TiCl4 和一当量的 HCl 水溶液反应，这些化合物以良好的产率转化为碳...

  DOI：

  10.1139/v94-022

文献信息

• Inhibition of the mammalian .beta.-lactamase renal dipeptidase (dehydropeptidase-I) by Z-2-(acylamino)-3-substituted-propenoic acids
  作者：Donald W. Graham、Wallace T. Ashton、Louis Barash、Jeannette E. Brown、Ronald D. Brown、Laura F. Canning、Anna Chen、James P. Springer、Edward F. Rogers

  DOI：10.1021/jm00389a018

  日期：1987.6

  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.
• O-Methylarenehydroxamates as ortho-lithiation directing groups. Titanium(III)-mediated conversion of O-methyl hydroxamates to primary amides
  作者：Lawrence E. Fisher、Joan M. Caroon、Jahangir、S. Russell Stabler、Scott Lundberg、Joseph M. Muchowski

  DOI：10.1021/jo00066a014

  日期：1993.7

  Reaction of O-methyl benzohydroxamates 2a-c with sec-butyllithium in the presence of TMEDA at -40-degrees-C regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g. 3). These dilithio species react avidly with a wide spectrum of electrophilic reagents, including alkyl halides, giving adducts which on reduction with TiCl3 are converted into ortho-substituted primary benzamides in excellent yields. Ortho lithiation of O-methyl benzohydroxamates is thus formally equivalent to ortho lithiation of primary benzamides themselves. The utility of these synthetic operations is enhanced by the well-known facility with which the primary amide moiety can be transformed into other useful functional groups. The conversion of 0-methyl hydroxamates to primary amides is shown to be general, as exemplified by transformation of 14a-f to 15a-f.O-Methyl 2-methylbenzohydroxamate (4a) undergoes regiospecific dilithiation on nitrogen and on the methyl group when treated with sec-butyllithium at -70-degrees-C. These dilithio species react with DMF or ''Weinreb-type'' amides to give condensation products which cyclize to N-methoxyisoquinolin-1(2H)-ones under mildly acidic conditions. Removal of the N-methoxy moiety under conditions analogous to those used for O-methyl benzohydroxamate provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency. This process is exemplified by the synthesis of isoquinolin-1(2H)-one 9a, its 3-n-butyl congener 9b, and the tricyclic isoquinolin-1 (2H)-ones 20a and 20b from O-methyl 2-methylbenzohydroxamate (4a).
• Fisher Lawrence E., Caroon Joan M., Stabler S. Russell, Lundberg Scott, Z+, Can. J. Chem, 72 (1994) N 1, S 142-145
  作者：Fisher Lawrence E., Caroon Joan M., Stabler S. Russell, Lundberg Scott, Z+

  DOI：——

  日期：——
• US4133949A
  申请人：——

  公开号：US4133949A

  公开（公告）日：1979-01-09
• US4282151A
  申请人：——

  公开号：US4282151A

  公开（公告）日：1981-08-04