octyl 2-(2-(carboxymethyl)phenyl)-2-oxoacetic ester | 1415100-72-9

• 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: octyl 2-(2-(carboxymethyl)phenyl)-2-oxoacetic ester
• 英文别名: 2-[2-(2-Octoxy-2-oxoacetyl)phenyl]acetic acid；2-[2-(2-octoxy-2-oxoacetyl)phenyl]acetic acid
• CAS: 1415100-72-9
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: NMEBUIDLKXFIDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1H-茚-3-羧酸 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 臭氧 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 12.0h， 生成 octyl 2-(2-(carboxymethyl)phenyl)-2-oxoacetic ester
  参考文献：
  名称：

  Synthesis of the 1-Monoester of 2-Ketoalkanedioic Acids, for Example, Octyl α-Ketoglutarate

  摘要：

  Oxidative cleavage of cycloalkene-1-carboxylates, made from the corresponding carboxylic acids, and subsequent oxidation of the resulting ketoaldehyde afforded the important 1-monoesters of 2-ketoalkanedioic acids. Thus ozonolysis of octyl cyclobutene-1-carboxylate followed by sodium chlorite oxidation afforded the 1-monooctyl 2-ketoglutarate. This is a cell-permeable prodrug form of alpha-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right.

  DOI：

  10.1021/jo302308q

文献信息

• Synthesis of the 1-Monoester of 2-Ketoalkanedioic Acids, for Example, Octyl α-Ketoglutarate
  作者：Michael E. Jung、Gang Deng

  DOI：10.1021/jo302308q

  日期：2012.12.7

  Oxidative cleavage of cycloalkene-1-carboxylates, made from the corresponding carboxylic acids, and subsequent oxidation of the resulting ketoaldehyde afforded the important 1-monoesters of 2-ketoalkanedioic acids. Thus ozonolysis of octyl cyclobutene-1-carboxylate followed by sodium chlorite oxidation afforded the 1-monooctyl 2-ketoglutarate. This is a cell-permeable prodrug form of alpha-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right.