二(2,6-二甲苯基)二硫醚 | 2905-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二(2,6-二甲苯基)二硫醚
• 英文名称: bis(2,6-dimethylphenyl)disulfide
• 英文别名: 1,2-bis(2,6-dimethylphenyl)disulfane；Disulfide, bis(2,6-dimethylphenyl)；2-[(2,6-dimethylphenyl)disulfanyl]-1,3-dimethylbenzene
• CAS: 2905-17-1
• 化学式: C₁₆H₁₈S₂
• 分子量: 274.451
• InChiKey: LKOHGPFWLCKZQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  二(2,6-二甲苯基)二硫醚 在 氯化亚砜 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.17h， 生成 ethyl 5-chloro-3-((2,6-dimethylphenyl)sulfonyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Indolylarylsulfones Carrying a Heterocyclic Tail as Very Potent and Broad Spectrum HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  We synthesized new indolylarylsulfone (IAS) derivatives carrying a heterocyclic tail at the indole-2-carboxamide nitrogen as potential anti-HIV/AIDS agents. Several new IASs yielded EC50 values <1.0 nM against HIV-1 WT and mutant strains in MT-4 cells. The (R)-11 enantiomer proved to be exceptionally potent against the whole viral panel; in the reverse transcriptase (RT) screening assay, it was remarkably superior to NVP and EFV and comparable to ETV. The binding poses were consistent with the one previously described for the IAS non-nucleoside reverse transcriptase inhibitors. Docking studies showed that the methyl group of (R)-11 points toward the cleft created by the K103N mutation, different from the corresponding group of (S)-11. By calculating the solvent-accessible surface, we observed that the exposed area of RT in complex with (S)-11 was larger than the area of the (R)-11 complex. Compounds 6 and 16 and enantiomer (R)-11 represent novel robust lead compounds of the IAS class.

  DOI：

  10.1021/jm5011622
• 作为产物：
  描述：

  1,3-二甲基-2-碘苯 在 copper(II) acetate monohydrate 、 potassium carbonate 、 巯基乙酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 以77 %的产率得到二(2,6-二甲苯基)二硫醚
  参考文献：
  名称：

  使用巯基乙酸和铜催化剂溶剂选择性合成二芳基二硫化物和芳硫基乙酸

  摘要：

  开发了一种使用巯基乙酸作为硫源从芳基碘化物合成二芳基二硫化物的有效铜催化方案。这种转化仅在含水 DMSO 中成功，当溶剂系统切换到含水 DMF 时，得到芳硫基乙酸，即直接的 C-S 偶联产物。每个合成方案都经过优化并应用于各种芳基碘化物，以良好至优异的收率提供相应的产物。

  DOI：

  10.1055/a-2178-1701

文献信息

• Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base
  作者：Tanmay Chatterjee、Brindaban C. Ranu

  DOI：10.1039/c3ra41996g

  日期：——

  An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields.

  在没有任何催化剂、共氧化剂、溶剂或碱的情况下，通过球磨中性氧化铝（研磨辅助剂），实现了硫醇到二硫化物的有效有氧化学选择性氧化。多种功能化的二芳基、二杂芳基和二烷基二硫化物以高产率获得。
• Oxidation of Thiols to Disulfides Using Silica Chloride as a Heterogeneous Catalyst
  作者：Manisha Sathe、Ramarao Ghorpade、Mahabir Parshad Kaushik

  DOI：10.1246/cl.2006.1048

  日期：2006.9

  Silica chloride is used as a selective and effective heterogeneous catalyst for the rapid conversion of thiols to disulfides with quantitative yields in a very short period of time.

  氯化硅用作选择性和有效的多相催化剂，用于在很短的时间内以定量收率快速将硫醇转化为二硫化物。
• Efficient Oxidative Coupling of Thiols into Disulfides Using<i>N</i>-<i>tert</i>-Butyl-<i>N</i>-chlorocyanamide
  作者：Vinod Kumar、Mahabir Parshad Kaushik

  DOI：10.1246/bcsj.81.160

  日期：2008.1.15

  Reaction of aliphatic/aromatic/heterocyclic thiols with N-tert-butyl-N-chlorocyanamide in presence of sodium bromide is described. The reaction was very rapid and resulted in the formation of disul...

  描述了脂肪族/芳香族/杂环硫醇与 N-叔丁基-N-氯氰胺在溴化钠存在下的反应。反应非常迅速，导致形成二硫...
• Sequential C–H activation enabled expedient delivery of polyfunctional arenes
  作者：Wensen Ouyang、Xiaoqing Cai、Xiaojian Chen、Jie Wang、Jianhang Rao、Yang Gao、Yanping Huo、Qian Chen、Xianwei Li

  DOI：10.1039/d1cc03243g

  日期：——

  Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C–H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction

  从丰富的原料中模块化构建多功能芳烃是合成化学的不懈追求，加速了药物和材料的发现。在此，使用多功能亚胺酸酯的多重 C-H 活化策略，实现了密集功能化的含硫芳烃分子库的便捷传递，从而能够简明地构建生物活性分子，如双苯萘酚。
• Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS₂
  作者：Jing Leng、Shi-Meng Wang、Hua-Li Qin

  DOI：10.3762/bjoc.13.91

  日期：——

  A highly efficient and chemoselective method for the synthesis of diaryl disulfides is developed via a visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields.

  通过可见光促进的易于获得的四氟硼酸芳族重氮鎓和CS2的偶联，开发了一种高效的化学选择性合成二芳基二硫化物的方法。该实用且方便的方案为以环境友好的方式以良好或优异的收率组装一系列二硫化物提供了直接途径。