2-oxocyclopentane dithiocarboxylic acid | 57624-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxocyclopentane dithiocarboxylic acid
• 英文别名: 2-Oxocyclopentadiendithiocarbonsaeure；2-Oxocyclopentan-dithiocarbonsaeure；2-Oxocyclopentandithiocarbonsaeure；2-Oxocyclopentane-1-carbodithioic acid
• CAS: 57624-68-7
• 化学式: C₆H₈OS₂
• 分子量: 160.261
• InChiKey: HOHZONNFXVDJTG-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  263.8±50.0 °C(Predicted)
• 密度：
  1.62 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxocyclopentane dithiocarboxylic acid 在 咪唑 、 N-氯代丁二酰亚胺 、 双(三甲基硫化硅) 作用下， 生成 5,6-二氢-4H-环戊并[1,2]二硫代-3-硫酮
  参考文献：
  名称：

  Synthesis of 3H-1,2-dithiole-3-thiones by a novel oxidative cyclization

  摘要：

  Reaction of 3-oxo dithioic acids with a combination of hexamethyldisilathiane and N-chlorosuccinimide in the presence of a catalytic amount of imidazole brings about oxidative ring closure to 3H-1,2-dithiole-3-thiones. Yields vary from poor to good.

  DOI：

  10.1016/s0040-4039(00)79295-1
• 作为产物：
  描述：

  二硫化碳 、 环戊酮 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.0h， 生成 2-oxocyclopentane dithiocarboxylic acid
  参考文献：
  名称：

  Synthesis of 3H-1,2-dithiole-3-thiones by a novel oxidative cyclization

  摘要：

  Reaction of 3-oxo dithioic acids with a combination of hexamethyldisilathiane and N-chlorosuccinimide in the presence of a catalytic amount of imidazole brings about oxidative ring closure to 3H-1,2-dithiole-3-thiones. Yields vary from poor to good.

  DOI：

  10.1016/s0040-4039(00)79295-1

文献信息

• Thermal analysis of 2-oxocyclopentanedithiocarboxylato complexes of iron(iii), copper(ii) and zinc(ii) containing pyridine or morpholine as the second ligand
  作者：R. K. Verma、L. Verma、M. Ranjan、B. P. Verma、S. C. Mojumdar

  DOI：10.1007/s10973-008-9183-z

  日期：2008.10

  A series of ternary complexes of the types M2L′2L″2;ML′2L″2 (M=Fe, Cu, Zn; L′=2-oxocyclopentane dithiocarboxylate; L″=pyridine, morpholine) and CuL′2H2O was prepared afresh. Except the iron complex, all are dimer and complexation is through the dithio moiety of the ligand L′. Their thermal decomposition was carried out in air at heating rate 10°C min−1 and it revealed that the dehydration of the aqua complex follows the same path as the carboxylates and the pyridine complexes have the tendency to follow one-step decomposition. The copper complexes are less thermally stable. The overall thermal stability of the 2-oxocyclopentanedithiocarboxylato complexes of the three metals with the volatile ligands was found to be in the order: (CuLmorph)2< CuL2H2O<(CuLpy)2<(ZnLmorph)2<(ZnLpy)2

  一系列三元复合物，类型为 M2L′2L″2、ML′2L″2（M=Fe、Cu、Zn；L′=2-氧环戊二硫羧酸盐；L″=吡啶、吗啉）和 CuL′2H2O，被新鲜制备。除铁复合物外，所有复合物均为二聚体，配体 L′ 通过二硫部分进行配位。在加热速率为 10°C min−1 的空气中进行热分解，结果表明水合物复合物脱水过程与羧酸盐复合物相同，而吡啶复合物倾向于一步分解。铜复合物的热稳定性较低。三种金属与挥发性配体形成的 2-氧环戊二硫羧酸盐复合物整体热稳定性顺序为：(CuLmorph)2 < CuL2H2O < (CuLpy)2 < (ZnLmorph)2 < (ZnLpy)2。
• Synthesis of 3H-1,2-dithiole-3-thiones by a novel oxidative cyclization
  作者：Thomas J. Curphey、H.Howard Joyner

  DOI：10.1016/s0040-4039(00)79295-1

  日期：1993.11

  Reaction of 3-oxo dithioic acids with a combination of hexamethyldisilathiane and N-chlorosuccinimide in the presence of a catalytic amount of imidazole brings about oxidative ring closure to 3H-1,2-dithiole-3-thiones. Yields vary from poor to good.
• TAKESHIMA T.; FUKADA N.; OKABE E.; MINESHIMA F.; MURAOKA M., J. CHEM. SOC. PERKIN TRANS. PART I, <JCPK-BH>, 1975, NO 13, 1277-1279
  作者：TAKESHIMA T.、 FUKADA N.、 OKABE E.、 MINESHIMA F.、 MURAOKA M.

  DOI：——

  日期：——
• TAKESHIMA T.; MURAOKA M.; FUKADA N.; TAKAYAMA A.; YAMAMOTO T., J. ORG. CHEM. <JOCE-AH>, 1977, 42, NO 21, 3383-3386
  作者：TAKESHIMA T.、 MURAOKA M.、 FUKADA N.、 TAKAYAMA A.、 YAMAMOTO T.

  DOI：——

  日期：——
• A new synthesis of 3H-1,2-dithiole-3-thiones
  作者：Thomas J. Curphey、H.Howard Joyner

  DOI：10.1016/s0040-4039(00)79205-7

  日期：1993.6

  Exposure of 3-oxo dithioic acids to a solution of polysulfanes in liquid hydrogen sulfide gives 3H-1,2-dithiole-3-thiones in yields varying from poor to excellent. The method tolerates the presence of functional groups which are problematical for other methods of synthesis.