2-(methyldisulfanyl)thiophene | 1099615-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(methyldisulfanyl)thiophene
• 英文别名: 2-(Methyldithio)thiophene
• CAS: 1099615-39-0
• 化学式: C₅H₆S₃
• 分子量: 162.301
• InChiKey: WRASPQWAKZMYQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩硫醇 、 二甲基二硫 在 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以47%的产率得到2-(methyldisulfanyl)thiophene
  参考文献：
  名称：

  PdCl 2 / DMSO催化的巯基-二硫键交换：不对称二硫键的合成

  摘要：

  通过使用简单的PdCl 2 / DMSO催化系统与对称的二硫化物进行硫醇交换，可以有效地制备不对称的二硫化物。给定的方法具有出色的官能团耐受性，广泛的底物范围和操作简便性。该反应对于诸如肽和药物之类的生物活性支架的后期功能化特别有用。还已经制备了含二硫化物的有机染料。这种转化可以扩展到硫醇-二硒化物或硫醇-二碲化物交换，从而提供RS-SeR'或RS-TeR'。

  DOI：

  10.1021/acs.orglett.1c00858

文献信息

• 非对称二硫醚类化合物的制备方法
  申请人：上海大学

  公开号：CN112047902B

  公开（公告）日：2022-11-18

  本发明涉及一种非对称二硫醚类化合物的合成方法。本发明以方便易得的硫醇及对称的二硫醚化合物为原料，在钯盐或铜盐的催化作用下，高效地合成非对称的二硫醚类化合物。该方法具有原料易得、催化体系简单、操作方便、官能团兼容性好、产率高等优点。该方法尤其适合在复杂底物中选择性地引入二硫键，将在药物和食品等行业中得到广泛的应用。
• An (NH₄)₂S₂O₈-promoted cross-coupling of thiols/diselenides and sulfoxides for the synthesis of unsymmetrical disulfides/selenosulfides
  作者：Yang-Tong Ma、Chao Lin、Xiao-Bo Huang、Miao-Chang Liu、Yun-Bing Zhou、Hua-Yue Wu

  DOI：10.1039/d2cc01344d

  日期：——

  An (NH4)2S2O8-promoted cross-coupling of thiols/diselenides and sulfoxides to construct unsymmetrical disulfides/selenosulfides is disclosed. Control experiments demonstrate that (NH4)2S2O8 acts as an acid and an oxidant, while both ionic and radical routes are involved in the reaction. The KIE experiments reveal that C–H bond cleavage of sulfoxides was involved in the turnover-limiting step.

  公开了一种(NH 4 ) 2 S 2 O 8促进的硫醇/二硒化物和亚砜的交叉偶联以构建不对称的二硫化物/硒硫化物。对照实验表明，(NH 4 ) 2 S 2 O 8充当酸和氧化剂，而离子和自由基途径都参与反应。KIE 实验表明，亚砜的 C-H 键断裂参与了周转限制步骤。
• Bioactive Pyridine-<i>N</i>-oxide Disulfides from <i>Allium stipitatum</i>
  作者：Gemma O’Donnell、Rosemarie Poeschl、Oren Zimhony、Mekala Gunaratnam、Joao B. C. Moreira、Stephen Neidle、Dimitrios Evangelopoulos、Sanjib Bhakta、John P. Malkinson、Helena I. Boshoff、Anne Lenaerts、Simon Gibbons

  DOI：10.1021/np800572r

  日期：2009.3.27

  From Allium stipitatum, three pyridine-N-oxide alkaloids (1-3) possessing disulfide functional groups were isolated. The structures of these natural products were elucidated by spectroscopic means as 2-(methyldithio)pyridine-N-oxide (1), 2-[(methylthiomethyl)dithio]pyridine-N-oxide (2), and 2,2'-dithio-bis-pyridine-N-oxide (3). The proposed structure of 1 was confirmed by synthetic S-methylthiolation of commercial 2-thiopyridine-N-oxide. Compounds 1 and 2 are new natural products, and 3 is reported for the first time from an Allium species. All compounds were evaluated for activity against fast-growing species of Mycobacterium, methicillin-resistant Staphylococcus aureus, and a multidrug-resistant (MDR) variants of S. aureus. Compounds 1 and 2 exhibited minimum inhibitory concentrations (MICs) of 0.5-8 mu g/mL against these strains. A small series of analogues of 1 were synthesized in an attempt to optimize antibacterial activity, although the natural product had the most potent in vitro activity. In a whole-cell assay at 30 mu g/mL, 1 was shown to give complete inhibition of the incorporation of C-14-labeled acetate into soluble fatty acids, indicating that it is potentially an inhibitor of fatty acid biosynthesis. In a human cancer cell line antiproliferative assay, 1 and 2 displayed IC50 values ranging from 0.3 to 1.8 mu M with a selectivity index of 2.3 when compared to a human somatic cell line. Compound 1 was evaluated in a microarray analysis that indicated a similar mode of action to menadione and 8-quinolinol by interfering with the thioredoxin system and up-regulating the production of various heat shock proteins. This compound was also assessed in a mouse model for in vivo toxicity.
• PdCl₂/DMSO-Catalyzed Thiol–Disulfide Exchange: Synthesis of Unsymmetrical Disulfide
  作者：Jimin Guo、Jianjian Zha、Tao Zhang、Chang-Hua Ding、Qitao Tan、Bin Xu

  DOI：10.1021/acs.orglett.1c00858

  日期：2021.4.16

  Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially useful for late-stage functionalization of bioactive scaffolds such as peptides and pharmaceuticals.

  通过使用简单的PdCl 2 / DMSO催化系统与对称的二硫化物进行硫醇交换，可以有效地制备不对称的二硫化物。给定的方法具有出色的官能团耐受性，广泛的底物范围和操作简便性。该反应对于诸如肽和药物之类的生物活性支架的后期功能化特别有用。还已经制备了含二硫化物的有机染料。这种转化可以扩展到硫醇-二硒化物或硫醇-二碲化物交换，从而提供RS-SeR'或RS-TeR'。