((methyl)dithio)carbonyl chloride | 13063-89-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: ((methyl)dithio)carbonyl chloride
• 英文别名: (Methyldithio)carbonyl Chloride；S-methylsulfanyl chloromethanethioate
• CAS: 13063-89-3
• 化学式: C₂H₃ClOS₂
• 分子量: 142.63
• InChiKey: DTAKQGMOEJSQGN-UHFFFAOYSA-N

物化性质

• 沸点：
  55 °C(Press: 22 Torr)
• 密度：
  1.455±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((methyl)dithio)carbonyl chloride 以100%的产率得到
  参考文献：
  名称：

  MOTT, A. W.;BARANY, G., J. CHEM. SOC. PERKIN TRANS., 1984, N 11, 2615-2621

  摘要：

  DOI：
• 作为产物：
  描述：

  甲氧基二硫代甲酸甲酯 生成 ((methyl)dithio)carbonyl chloride
  参考文献：
  名称：

  MOTT, A. W.;BARANY, G., J. CHEM. SOC. PERKIN TRANS., 1984, N 11, 2615-2621

  摘要：

  DOI：

文献信息

• Synthetic Routes to, Transformations of, and Rather Surprising Stabilities of (<i>N</i>-Methyl-<i>N</i>-phenylcarbamoyl)sulfenyl Chloride, ((<i>N</i>-Methyl-<i>N</i>-phenylcarbamoyl)dithio)carbonyl Chloride, and Related Compounds
  作者：Alex M. Schrader、Alayne L. Schroll、George Barany

  DOI：10.1021/jo201329n

  日期：2011.10.7

  The title compound classes, (carbamoyl)sulfenyl chlorides and ((carbamoyl)dithio)carbonyl chlorides, have been implicated previously as unstable, albeit trappable, intermediates in organosulfur chemistry. The present work reports for each of these functional groups: (i) several routes to prepare it in the N-methylaniline family; (ii) its direct structural characterization by several spectroscopic techniques;

  先前已经将标题化合物类别（（氨基甲酰基）亚磺酰氯和（（氨基甲酰基）二硫代）羰基氯）认为是有机硫化学中不稳定的，尽管可捕集的中间体。本工作报告了这些官能团的每一个：（i）在N-甲基苯胺家族中制备它的几种途径；（ii）通过几种光谱技术对其结构进行直接表征；（iii）其相当意外的稳定性以及其分解时的最终命运；（iv）一系列进一步的化学转化，产生高度稳定的衍生物，每个衍生物都经过全面表征。进行了相关的动力学和机理实验，包括一些被对甲基和2,6-二甲基取代的N-甲基苯胺。鉴于标题化合物可以分离并且相对稳定，它们可以在制备用于半胱氨酸的巯基功能的硫解和/或光不稳定保护基中以及在开发新的蛋白质合成和修饰试剂中找到应用。
• A general strategy for elaboration of the dithiocarbonyl functionality, -(C:O)SS-: application to the synthesis of bis(chlorocarbonyl)disulfane and related derivatives of thiocarbonic acids
  作者：George Barany、Alayne L. Schroll、Andrew W. Mott、David A. Halsrud

  DOI：10.1021/jo00172a056

  日期：1983.12
• Mott, Andrew W.; Barany, George, Journal of the Chemical Society. Perkin transactions I, 1984, # 11, p. 2615 - 2621
  作者：Mott, Andrew W.、Barany, George

  DOI：——

  日期：——
• Vibrational spectra and structures of halogencarbonyl alkyldisulfanes XC(O)SSR with X=F, Cl and R=CF3, CH3
  作者：Angelika Hermann、Sonia E. Ulic、Carlos O. Della Védova、Hans-Georg Mack、Heinz Oberhammer

  DOI：10.1016/s0022-1139(01)00515-2

  日期：2001.12

  The disulfides FC(O)SSCF3, ClC(O)SSCF3 and ClC(O)SSCH3 have been prepared by new synthetic routes. Infrared and Raman spectra have been recorded and assigned. From the vibrational spectra and from the gas electron diffraction experiment it was concluded that FC(O)SSCF3 exists as a mixture of syn- and anti-conformers (C=O synperiplanar/antiperiplanar to S-S bond). The main conformer (83(5)% and DeltaG degrees = G degrees (anti) - G degrees (syn) = 0.95(28) kcal mol(-1)) possesses syn-structure. The vibrational spectra of the chlorocarbonyl disulfanes are interpreted in terms of a single conformer, but small amounts (<5%) of a second conformer cannot be excluded. Quantum chemical calculations (HF, MP2, B3PW91 with 6-31G* basis sets) reproduce the experimental results (conformational properties, geometric structure and vibrational frequencies) satisfactorily. The predicted difference in Gibbs free energy, DeltaG degrees, for FC(O)SSCF3 varies between 0.8 and 1.5 kcal mol(-1), those for the chlorine derivatives are larger than 2.6 kcal mol(-1). (C) 2001 Elsevier Science B.V. All rights reserved.
• BARANY, G.;SCHROLL, A. L.;MOTT, A. W.;HALSRUD, D. A., J. ORG. CHEM., 1983, 48, N 24, 4750-4761
  作者：BARANY, G.、SCHROLL, A. L.、MOTT, A. W.、HALSRUD, D. A.

  DOI：——

  日期：——