meso-dimethyl 2,4-bis(acetylthio)glutarate | 1463952-97-7

• 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: meso-dimethyl 2,4-bis(acetylthio)glutarate
• 英文别名: dimethyl (2R,4S)-2,4-bis(acetylsulfanyl)pentanedioate
• CAS: 1463952-97-7
• 化学式: C₁₁H₁₆O₆S₂
• 分子量: 308.376
• InChiKey: USGRCPMOYMIUSR-DTORHVGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,4-二溴戊二酸二甲酯 、 potassium thioacetate 以 甲醇 为溶剂， 生成 meso-dimethyl 2,4-bis(acetylthio)glutarate 、 rac-dimethyl 2,4-bis(acetylthio)glutarate
  参考文献：
  名称：

  Structural characterization of 1,3-propanedithiols that feature carboxylic acids: Homologues of mercury chelating agents

  摘要：

  The molecular structures of a series of 1,3-propanedithiols that contain carboxylic acid groups, namely rac- and meso-2,4-dimercaptoglutaric acid (H(4)DMGA) and 2-carboxy-1,3-propanedithiol (H3DMCP), have been determined by X-ray diffraction. Each compound exhibits two centrosymmetric intermolecular hydrogen bonding interactions between pairs of carboxylic acid groups, which result in a dimeric structure for H3DMCP and a polymeric tape-like structure for rac- and meso-H(4)DMGA. Significantly, the hydrogen bonding motifs observed for rac- and meso-H(4)DMGA are very different to those observed for the 1,2-dithiol, rac-2,3-dimercaptosuccinic acid (rac-H(4)DMSA), in which the two oxygen atoms of each carboxylic acid group hydrogen bond to two different carboxylic acid groups, thereby resulting in a hydrogen bonded sheet-like structure rather than a tape. Density functional theory calculations indicate that 1,3-dithiolate coordination to mercury results in larger S-Hg-S bond angles than does 1,2-dithiolate coordination, but these angles are far from linear. As such, kappa(2)-S-2 coordination of these dithiolate ligands is expected to be associated with mercury coordination numbers of greater than two. In vivo studies demonstrate that both rac-H(4)DMGA and H3DMCP reduce the renal burden of mercury in rats, although the compounds are not as effective as either 2,3-dimercaptopropane-1-sulfonic acid (H3DMPS) or meso-H(4)DMSA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.05.012