3-Methyl-4-phenyl-1,3,4-thiadiazol-2(3H)-thion | 5770-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Methyl-4-phenyl-1,3,4-thiadiazol-2(3H)-thion
• 英文别名: 3-Methyl-5-phenyl-1,3,4-thiadiazol-2(3H)-thion；3-methyl-5-phenyl-3H-[1,3,4]thiadiazole-2-thione；3-methyl-5-phenyl-1,3,4-thiadiazole-2(3H)-thione；2-Phenyl-4-methyl-1,3,4-thiadiazolin-5-thion；5-Methyl-5-phenyl-1,3,4-thiadiazolin-2-thion；N-Methyl-5-phenyl-1,3,4-thiadiazolin-2-thion；1,3,4-Thiadiazole-2(3H)-thione, 3-methyl-5-phenyl-；3-methyl-5-phenyl-1,3,4-thiadiazole-2-thione
• CAS: 5770-97-8
• 化学式: C₉H₈N₂S₂
• 分子量: 208.308
• InChiKey: XFXHZWGGDQXLQO-UHFFFAOYSA-N

物化性质

• 熔点：
  125 °C
• 沸点：
  299.0±23.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-4-phenyl-1,3,4-thiadiazol-2(3H)-thion 、 碘甲烷 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Specific Molecular Orbital Contributions to Nucleophilicity. The Thiocarbonyl Group as Priviledged Monitor to Pinpoint Active and Less Active Molecular Orbitals in Reactions with Methylating Agents

  摘要：

  The rate constants for 41 compounds bearing a C=S function reacting with MeX (X = I, Tos) span 7 orders of magnitude. The PES spectra of these compounds display two very low energy peaks, which stand clearly apart from the other peaks. These two peaks correspond to the pi orbitals of the C-S group; one is its CS pi bonding orbital oriented out of the molecular plane (pi(CS)) and the other its p-type in-plane lone pair orbital (pi(S)). For some of the compounds, the HOMO is the pi(CS) orbital and for others the HOMO is the ns lone pair orbital. The best correlation (R = 0.96) between rate constants h and PES data is obtained when In(k) is plotted against the inverse of PES energy of the pi(S) lone pair orbital. Whether this lone pair orbital is the HOMO or the next lower HOMO has no importance. A modest correlation (R = 0.78) is obtained when In(k) is plotted against the inverse of PES energy of the pi(CS) bonding orbital, An attempt to correlate the calculated energy of the third highest occupied orbital (from AM1 calculations) with In(h) provides a complete scattering of data (R < 0.1), but the calculated energy of the second lone pair orbital sigma(S) (approximate to 90 kcal mol-l deeper than the HOMO) correlates reasonably with In(h) (R = 0.88). The energies of the S 2s and 2p core orbitals (calculated for 13 cyclic compounds with the HF/3-21G technique to be 4000 to 5500 kcal mol(-1) deeper than HOMO) correlate with In(k) (R = 0.86) as well as does that of the second lone pair orbital os. These results are the first where both frontier orbitals and core orbitals display correlation with overall reactivity. They are discussed in terms of direct (perturbational) versus indirect (nonperturbational) concepts.

  DOI：

  10.1021/jo00113a010
• 作为产物：
  描述：

  3-methyl-5-phenyl-2-thioxo-[1,3,4]thiadiazinane-6-one O-benzoyl-oxime 在 敌草腈 作用下， 以 乙腈 为溶剂， 生成 3-Methyl-4-phenyl-1,3,4-thiadiazol-2(3H)-thion
  参考文献：
  名称：

  Petersen,U.; Heitzer,H., Justus Liebigs Annalen der Chemie, 1973, p. 944 - 960

  摘要：

  DOI：

文献信息

• A synthetic approach to 1,3,4-thiadiazolidine-2-thiones
  作者：F.C. Heugebaert、J.F. Willems

  DOI：10.1016/0040-4020(66)80065-0

  日期：1966.1

  The course of the reaction between dithiocarbazic acid and aldehydes and ketones has been examined. Aliphatic and π-deficient heterocyclic aldehydes and ketones form 1,3,4-thiadiazolidine-2-thiones. Aromatic and π-excessive heterocyclic aldehydes and ketones, however, form azines. A similar course occurs in the reaction between the hydrazones and carbon disulphide.

  已经研究了二硫代咔唑酸与醛和酮之间的反应过程。脂肪族和π缺失的杂环醛和酮形成1,3,4-噻二唑烷-2-硫酮。但是，芳族和π过量的杂环醛和酮会形成嗪。hydr与二硫化碳之间的反应过程类似。
• Photoreaktionen des 3-Methyl-4-phenylsydnons
  作者：Karl-Heinz Pfoertner、Joseph Foricher

  DOI：10.1002/hlca.19800630312

  日期：1980.4.23

  Photoreactions of 3-Methyl-4-phenylsydnone

  3-甲基-4-苯基亚砜的光反应
• Fliege, Werner; Grashey, Rudolf; Huisgen, Rolf, Chemische Berichte, 1984, vol. 117, # 3, p. 1194 - 1214
  作者：Fliege, Werner、Grashey, Rudolf、Huisgen, Rolf

  DOI：——

  日期：——
• Sandstroem,J.; Wennerbeck,I., Acta Chemica Scandinavica (1947), 1966, vol. 20, p. 57 - 71
  作者：Sandstroem,J.、Wennerbeck,I.

  DOI：——

  日期：——
• Muehlstaedt, Manfred; Weber, Lutz, Zeitschrift fur Chemie, 1985, vol. 25, # 9, p. 323
  作者：Muehlstaedt, Manfred、Weber, Lutz

  DOI：——

  日期：——