rac-1,2-dithiolane-3,5-dicarboxylic acid | 1126-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: rac-1,2-dithiolane-3,5-dicarboxylic acid
• 英文别名: (+/-)-trans-[1,2]dithiolane-3,5-dicarboxylic acid；(+/-)-trans-[1,2]Dithiolan-3,5-dicarbonsaeure；(3S,5S)-dithiolane-3,5-dicarboxylic acid
• CAS: 1126-47-2；19307-93-8；31413-40-8；31413-55-5；60208-68-6
• 化学式: C₅H₆O₄S₂
• 分子量: 194.232
• InChiKey: OBKGJBFGGPSACP-HRFVKAFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  rac-1,2-dithiolane-3,5-dicarboxylic acid 在 碳酸氢钠 、 锌 、 盐酸 作用下， 以 水 为溶剂， 反应 0.5h， 以71%的产率得到rac-2,4-dimercaptoglutaric acid
  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
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 sodium disulfide 作用下， 生成 rac-1,2-dithiolane-3,5-dicarboxylic acid
  参考文献：
  名称：

  Schotte, Arkiv foer Kemi, 1956, vol. 9, p. 441,458

  摘要：

  DOI：

文献信息

• Schotte, Arkiv foer Kemi, 1955, vol. 8, p. 579,583
  作者：Schotte

  DOI：——

  日期：——
• Structural characterization of 1,3-propanedithiols that feature carboxylic acids: Homologues of mercury chelating agents
  作者：Wesley Sattler、Joshua H. Palmer、Christy C. Bridges、Lucy Joshee、Rudolfs K. Zalups、Gerard Parkin

  DOI：10.1016/j.poly.2013.05.012

  日期：2013.11

  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.
• Schotte, Arkiv foer Kemi, 1956, vol. 9, p. 441,458
  作者：Schotte

  DOI：——

  日期：——