4-(bis(methylthio)methylene)-1,3-diphenyl-1H-pyrazol-5(4H)-one | 55675-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 4-(bis(methylthio)methylene)-1,3-diphenyl-1H-pyrazol-5(4H)-one
• 英文别名: 4-(bis-methylsulfanyl-methylene)-2,5-diphenyl-2,4-dihydro-pyrazol-3-one；1,3-Diphenyl-4-bis-(methylthio)-methylen-2-pyrazolin-5-on；4-[Bis(methylsulfanyl)methylidene]-2,5-diphenylpyrazol-3-one
• CAS: 55675-58-6
• 化学式: C₁₈H₁₆N₂OS₂
• 分子量: 340.47
• InChiKey: TUGNIYSVMUOQFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  113-115 °C(Solv: ligroine (8032-32-4))
• 沸点：
  436.0±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(bis(methylthio)methylene)-1,3-diphenyl-1H-pyrazol-5(4H)-one 在 potassium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 5.0h， 生成 1,3-diphenyl-6-methylthio-2,3,7-triazaspiro<4,4>non-1,6-dien-4-one
  参考文献：
  名称：

  Basaveswara Rao; Suresh; Kumar, Arvind, Journal of the Indian Chemical Society, 1997, vol. 74, # 11-12, p. 955 - 960

  摘要：

  DOI：
• 作为产物：
  描述：

  二硫化碳 、 2,4-二氢-2,5-二苯基-3H-吡唑啉-3-酮 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以29%的产率得到4-(bis(methylthio)methylene)-1,3-diphenyl-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  Synthesis, spectral, crystal and theoretical studies of some novel 4-heterocyclic substituted pyrazolones

  摘要：

  Reactions of pyrazolone ketene dithioacetals with various binucleophiles afforded 4-heterocyclic substituted pyrazolone compounds as ketene N,N-, N,O-acetals in the absence of any acid/base catalyst in good yields. The products 3a-i formed by the direct displacement of dithioacetals exhibited high regioselectivity towards binucleophiles. All the synthesized compounds were characterized by IR, H-1, C-13, 2D NMR and X-ray diffraction techniques. Optimized geometry of compound 3e has been computed by Density Functional Theory (DFT) method in B3LYP 6-31G** level basis set. The title compounds 3d-f were crystallized in monoclinic space group Pc, P2(1)/n, P2(1)/c with cell parameters: a = 76647(3), b = 26.7020(8), c = 12.8364(5)angstrom', beta = 102.842(4)degrees, V = 2561.42(16)angstrom(3'), Z = 9 (for 3d), a = 13.448(5), b = 7.539(5), c = 14.832(5) angstrom', beta = 94.747(5)degrees, V = 1498.6(12)angstrom(3'), Z = 4 (for 3e) and a = 13.6468(17), b = 15.905(2), c = 7.9029(9)angstrom', beta = 100.774(9)degrees, V = 1685.1(4)angstrom(3'), Z = 4 (for 3f) respectively. The spectral and crystal studies revealed that the compounds 3a-i exist in amine-one tautomeric form in solid state and the optimized structure T5 of the compound 3e exhibit good agreement with X-ray diffraction data. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.10.018

文献信息

• A New General Method for the Synthesis of 1,3-Disubstituted 5-Cyano-4-methylthio-6-oxo-1,6-dihydropyrano[2,3-<i>c</i>]pyrazoles Using α-Ketoketene<i>S</i>,<i>S</i>-Acetals¹
  作者：A. KUMAR、H. ILA、H. JUNJAPPA

  DOI：10.1055/s-1976-24036

  日期：——
• AUZZI G.; PAPINI P.; PECORI VETTORI L., BOLL. CHIM. FARM. <BCFA-AT>, 1974, 113, NO 12, 633-641
  作者：AUZZI G.、 PAPINI P.、 PECORI VETTORI L.

  DOI：——

  日期：——
• KUMAR A.; ILA H.; JUNGJAPPA H.; MHATRE S., J. CHEM. SOC. CHEM. COMMUNS <CCOM-A8>, 1976 NO 15, 592-593
  作者：KUMAR A.、 ILA H.、 JUNGJAPPA H.、 MHATRE S.

  DOI：——

  日期：——
• Synthesis, spectral, crystal and theoretical studies of some novel 4-heterocyclic substituted pyrazolones
  作者：Kuppusamy Narayanan、Mani Shanmugam、Gnanasambandam Vasuki、Senthamaraikannan Kabilan

  DOI：10.1016/j.molstruc.2013.10.018

  日期：2014.1

  Reactions of pyrazolone ketene dithioacetals with various binucleophiles afforded 4-heterocyclic substituted pyrazolone compounds as ketene N,N-, N,O-acetals in the absence of any acid/base catalyst in good yields. The products 3a-i formed by the direct displacement of dithioacetals exhibited high regioselectivity towards binucleophiles. All the synthesized compounds were characterized by IR, H-1, C-13, 2D NMR and X-ray diffraction techniques. Optimized geometry of compound 3e has been computed by Density Functional Theory (DFT) method in B3LYP 6-31G** level basis set. The title compounds 3d-f were crystallized in monoclinic space group Pc, P2(1)/n, P2(1)/c with cell parameters: a = 76647(3), b = 26.7020(8), c = 12.8364(5)angstrom', beta = 102.842(4)degrees, V = 2561.42(16)angstrom(3'), Z = 9 (for 3d), a = 13.448(5), b = 7.539(5), c = 14.832(5) angstrom', beta = 94.747(5)degrees, V = 1498.6(12)angstrom(3'), Z = 4 (for 3e) and a = 13.6468(17), b = 15.905(2), c = 7.9029(9)angstrom', beta = 100.774(9)degrees, V = 1685.1(4)angstrom(3'), Z = 4 (for 3f) respectively. The spectral and crystal studies revealed that the compounds 3a-i exist in amine-one tautomeric form in solid state and the optimized structure T5 of the compound 3e exhibit good agreement with X-ray diffraction data. (C) 2013 Elsevier B.V. All rights reserved.
• Basaveswara Rao; Suresh; Kumar, Arvind, Journal of the Indian Chemical Society, 1997, vol. 74, # 11-12, p. 955 - 960
  作者：Basaveswara Rao、Suresh、Kumar, Arvind、Ila、Junjappa

  DOI：——

  日期：——