2-mercapto-4-methyl-4,5-dihydro-1,3,4-thiadiazole-5-thione | 29546-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-mercapto-4-methyl-4,5-dihydro-1,3,4-thiadiazole-5-thione
• 英文别名: 2-mercapto-4-methyl-1,3,4-thiadiazoline-5-thione；3-methyl-[1,3,4]thiadiazolidine-2,5-dithione；5-Mercapto-3-methyl-1,3,4-thiadiazol-2(3H)-thion；2-Mercapto-4-methyl-5-thioxo-1.3.4-thiadiazolin；3-methyl-1,3,4-thiadiazolidine-2,5-dithione
• CAS: 29546-26-7；70893-51-5
• 化学式: C₃H₄N₂S₃
• 分子量: 164.276
• InChiKey: NSBVDANJMHJPML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-mercapto-4-methyl-4,5-dihydro-1,3,4-thiadiazole-5-thione 生成 4-methyl-2-methylthio-4,5-dihydro-1,3,4-thiadiazole-5-thione
  参考文献：
  名称：

  ABSORPTION SPECTRA OF 2,5-DIMERCAPTO-1,3,4-THIADIAZOLE AND ITS METHYL DERIVATIVES

  摘要：

  通过使用N-和S-甲基衍生物，确定了2,5-二巯基-1,3,4-噻二唑三种互变异构体的吸收光谱。在紫外区域，当从二硫醇形式变为硫醇-硫醇形式，再变为二硫醇形式时，吸收峰出现了明显的红移。在红外区域1508-1475 cm^-1和1435-1415 cm^-1处的强吸收带分别被归属为[公式：见文本]。

  DOI：

  10.1139/v60-202
• 作为产物：
  描述：

  二硫化碳 、 甲基肼 在 氢氧化钾 作用下， 生成 2-mercapto-4-methyl-4,5-dihydro-1,3,4-thiadiazole-5-thione
  参考文献：
  名称：

  Busch; Ziegele, Journal fur praktische Chemie (Leipzig 1954), 1899, vol. <2> 60, p. 45

  摘要：

  DOI：

文献信息

• Semisynthetic .BETA.-lactam antibiotics. 8. Structure-activity relationships of .ALPHA.-sulfocephalosporins.
  作者：HIROAKI NOMURA、ISAO MINAMI、TAKENORI HITAKA、TAKESHI FUGONO

  DOI：10.7164/antibiotics.29.928

  日期：——

  Synthesis and in vitro activity of a number of cephalosporins having α-sulfoacyl- or other acyl groups, e.g., α-carboxyacyl- and α-sulfoaminoacyl- at the 7-position and bearing a variety of heterocyclic thioether or pyridinium moieties at the 3-position are described.

  介绍了一些头孢菌素的合成和体外活性，这些头孢菌素在 7 位上具有 α-磺酰基或其他酰基，如 α-羧酰基和 α-磺酰胺酰基，在 3 位上具有各种杂环硫醚或吡啶基。
• Chemistry of N-heterocyclic sulfur compounds. Reaction of 2,5-dimercapto-1,3,4-thiadiazoles with 1,.omega.-dibromoalkanes. Synthesis of tetrathia[(n + 2).(n + 2)](2,5)-1,3-4-thiadiazolophanes and dithia[(n + 1).(n + 1)](3,5)-1,3,4-thiadiazolinophanedithiones
  作者：Sebastiano Pappalardo、Francesco Bottino、Corrado Tringali

  DOI：10.1021/jo00379a017

  日期：1987.2
• Reiter, Jozsef; Barkoczy, Jozsef, Journal of Heterocyclic Chemistry, 1993, vol. 30, # 2, p. 333 - 343
  作者：Reiter, Jozsef、Barkoczy, Jozsef

  DOI：——

  日期：——
• Sandstroem, Arkiv foer Kemi, 1956, vol. 9, p. 255,267
  作者：Sandstroem

  DOI：——

  日期：——
• Electron impact inducedortho effects in 2-nitro-substituted aromatic sulphides containing 2-pyridyl, 2-(5-methylthio-1,3,4-thiadiazolyl) and/or 2-(4-methyl-1,3,4-thiadiazolinyl-5-thione) moieties
  作者：Sebastiano Pappalardo、Michele Di Grazia

  DOI：10.1002/oms.1210200603

  日期：1985.6

  AbstractThe most significant mass spectral features of 14 title compounds are discussed with the aid of deuterium labelling experiments. The decomposition patterns of these compounds are strongly affected by several competing ortho effects, due to the interaction of the nitro function(s) with neighbouring electron‐poor N‐heterocycles. Very intense polycyclic ions are produced via addition‐elimination reactions by loss of simple radicals (H˙, OH˙, NO2˙) from the molecular ion, followed by the ejection of neutral molecules (HNO2,CH3SCN or CH3NCS). In addition, primary or secondary intramolecular oxygen transfers, preceded or not by hydrogen migration, from the nitro group to the imino carbon via spirocyclic intermediates, are generally observed. Minor skeletal rearrangements, triggered by single or multiple intramolecular oxygen transfer to the bridgehead sulphur atom, followed by SO or SO2 ejection, are also noticed.

表征谱图