isopropyl isopropanethiosulfonate | 10027-69-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: isopropyl isopropanethiosulfonate
• 英文别名: di-isopropyl thiosulfonate；S-isopropyl propane-2-sulfonothioate；S-Isopropyl 2-propanesulphonothioate；2-propan-2-ylsulfonylsulfanylpropane
• CAS: 10027-69-7
• 化学式: C₆H₁₄O₂S₂
• 分子量: 182.308
• InChiKey: OZDMLIZXKUYGMR-UHFFFAOYSA-N

物化性质

• 沸点：
  96-97 °C(Press: 1-2 Torr)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isopropyl isopropanethiosulfonate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以47%的产率得到bis(2-propyl) disulfone
  参考文献：
  名称：

  Substitution reactions of alkanesulfonyl derivatives: direct substitution vs. elimination-addition mechanisms in substitution reactions of alkyl .alpha.-disulfones

  摘要：

  DOI：

  10.1021/ja00395a024
• 作为产物：
  描述：

  异丙基二硫醚 在 potassium permanganate absorbed on copper(II) sulfate pentahydrate (1:3) 作用下， 反应 0.06h， 以68%的产率得到isopropyl isopropanethiosulfonate
  参考文献：
  名称：

  Fast and efficient green synthesis of thiosulfonate S-esters by microwave-supported permanganate oxidation of symmetrical disulfides

  摘要：

  Potassium permanganate absorbed on copper(II) sulfate pentahydrate has been found to be an efficient, inexpensive, and green oxidation agent for the synthesis of "symmetrical" thiosulfonate S-esters by oxidation of the corresponding symmetrical disulfides. The oxidation reactions were carried out under solvent-free reaction conditions within 15 min under the influence of microwave irradiation, as well as (for comparison) supported by conventional heating, to afford yields of the thiosulfonate S-esters in the range of 60-83%. The oxidation reaction appears to proceed (at least partly) via an intermediate symmetrical vic-disulfoxide.

  DOI：

  10.1080/17415993.2015.1025404

文献信息

• Synthesis of symmetrical / unsymmetrical thiosulfonates through the disproportionate coupling reaction of sulfonyl hydrazide mediated by phosphomolybdic acid
  作者：Mengting Lv、Yufeng Liu、Ke Li、Guoping Yang

  DOI：10.1016/j.tetlet.2020.152757

  日期：2021.2

  catalyst for the synthesis of symmetrical / unsymmetrical thiosulfonates via the disproportionate coupling reaction of sulfonyl hydrazide. The attributes of this reported catalytic system include low catalyst loadings (1 mol%), efficient turnover, and high yields (up to 94%). Additionally, this reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via sulfinyl radical disproportionation

  据报道，磷钼酸（H 3 PMo 12 O 40）是一种绿色的低成本催化剂，可通过磺酰肼的不成比例的偶联反应合成对称/不对称的硫代磺酸盐。该报道的催化系统的特征包括低催化剂装载量（1mol％），有效的转化率和高产率（高达94％）。另外，该反应机理涉及通过亚磺酰基自由基歧化形成硫代自由基和磺酰基。
• 2-Amino-3-substituted-6-[(<i>E</i>)-1-phenyl-2-(<i>N</i>-methylcarbamoyl)vinyl]imidazo[1,2-<i>a</i>]pyridines as a Novel Class of Inhibitors of Human Rhinovirus:  Stereospecific Synthesis and Antiviral Activity
  作者：Chafiq Hamdouchi、Jesús de Blas、Mirian del Prado、Joseph Gruber、Beverly A. Heinz、Lori Vance

  DOI：10.1021/jm9810405

  日期：1999.1.1

  plaque reduction assay and in a cytopathic effect assay. Compounds 1b-d,h exhibited a strong antirhinovirus activity, and no apparent cellular toxicity was visible. The substitution at the 3-position was required for activity. Surprisingly the isopropylsulfonyl in this family of compounds did not enhance the activity as in the case of benzimidazoles. Instead, compound 1i was 4 times less active than its

  与结构相关的一系列2-氨基-3-取代-6-[（（E）-1-苯基-2-（N-甲基氨基甲酰基）乙烯基] + ++咪唑基偶氮[1,2-a]吡啶1a-i设计并制备了Enviroxime及其类似物苯并咪唑的抗鼻炎病毒药物。这类化合物中的咪唑环是从甲苯磺酰化后的氨基吡啶开始，然后用适当的乙酰胺进行处理而构建的。合成过程中的关键步骤包括开发和使用新的Horner-Emmons试剂直接掺入甲基乙烯基羧酰胺。该反应在底物5a-f中是立体特异性的，仅导致所需的E-异构体，并且避免在抗病毒活性评估之前避免使用反相制备型HPLC分离两种可能的异构体。异丙基磺酰基，在新系列的咪唑并[1,2-a]吡啶中，通过卤素-金属交换并随后用异丙基异丙基硫代磺酸磺酸盐进行处理，引入了在活性方面被称为苯并咪唑SAR 1-位最佳取代基的化合物。在菌斑减少测定和细胞病变效应测定中评价化合物1a-i。化合物1b-d，h表现出很强的抗鼻病
• Enantioselective Synthesis of Thiosulfinates and of Acyclic Alkylidenemethylene Sulfide Sulfoxides
  作者：Stefano Colonna、Vincenza Pironti、Jozef Drabowicz、Franck Brebion、Louis Fensterbank、Max Malacria

  DOI：10.1002/ejoc.200400892

  日期：2005.5

  Enantioselectivities up to 75 % have been found in the catalytic mono-oxidation of di-tert-butyl disulfide and related compounds as well as of ketene-S,S-acetals with an in situ generated chiral dioxirane. The effect of solvents on the enantiomeric excess has also been examined. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  在二叔丁基二硫化物和相关化合物以及乙烯酮-S,S-缩醛与原位生成的手性二环氧乙烷的催化单氧化反应中，已发现对映选择性高达 75%。还研究了溶剂对对映体过量的影响。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis of enantiomerically pure (R)- and (S)-2-ethoxycarbonylmethyl-2-hydroxy-cyclohexanones
  作者：José L Garcı́a Ruano、David Barros、M.Carmen Maestro、Ana Alcudia、Inmaculada Fernández

  DOI：10.1016/s0957-4166(98)00367-x

  日期：1998.10

  with thiosulfonates. The in situ aldol reaction of these compounds with ethyl acetate enolate is highly stereoselective (1,2-asymmetric induction) and yields diastereomeric mixtures of β-hydroxyesters (the configuration of the major one being dependent on the sulfenylating agent) that can be readily separated and transformed into the enantiomerically pure title ketones.

  2-对甲苯基亚磺酰基环己酮的亚磺酰基化可以在-78°C下用硫代磺酸盐实现。这些化合物与乙酸乙酯的烯醇盐的原位羟醛反应是高度立体选择性的（1,2-不对称诱导），可生成易于分离的β-羟基酯的非对映混合物（主要的构型取决于亚磺酰化剂）。并转化为对映体纯的标题酮。
• Reaction of thiolsulfinates with trihaloacetic anhydrides—I
  作者：Tsuyoshi Morishita、Naomichi Furukawa、Shigeru Oae

  DOI：10.1016/s0040-4020(01)98843-x

  日期：1981.1

  Thiolsulfinates react with trifluoro- or trichloroacetic anhydride to give equimolar mixtures of the corresponding disulfides and sulfinyl trifluoro- or trichloroacetates which are in equilibria with sulfenyl carboxylates. Although the equilibrium lies far toward sulfinyl carboxylates at room temperature, addition of olefins to the mixed solution of sulfinyl carboxylate and a corresponding disulfide

  硫亚磺酸盐与三氟或三氯乙酸酐反应，得到相应的二硫化物和亚硫酰基三氟乙酸或三氯乙酸盐的等摩尔混合物，它们与亚磺酰基羧酸盐处于平衡状态。尽管在室温下平衡远未达到亚磺酰基羧酸盐，但是将烯烃添加到亚磺酰基羧酸盐和相应的二硫化物的混合溶液中可提供在相应的亚磺酰基羧酸盐和烯烃之间的反应中形成的加合物。同时，用亚磺酰氯处理羧酸银盐也得到亚磺酰基羧酸盐，但是，尚未成功分离出亚磺酰基羧酸盐。

表征谱图