8–mercapto–1,2–dicarba–closo–dodecaborane | 69968-36-1

• 英文名称: 8–mercapto–1,2–dicarba–closo–dodecaborane
• 英文别名: 8-mercapto-1,2-dicarba-closo-dodecaborane
• CAS: 69968-36-1
• 化学式: C₂H₁₂B₁₀S
• 分子量: 176.293
• InChiKey: QAZQDGHRPABPCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  8–mercapto–1,2–dicarba–closo–dodecaborane 、 二苯基氯化膦 在 triethylamine 作用下， 以 乙醚 为溶剂， 以85%的产率得到S-(o-carboran-9-yl)diphenylthiophosphinite
  参考文献：
  名称：

  Synthesis, structure, and certain transformations of S-(o-carboran-9-yl) diphenylthiophosphinite

  摘要：

  S-(o-Carboran-9-yl) diphenylthiophosphinite was obtained for the first time and its structure and transformations were studied. A series of esters of thio- dithio- and selenothiophosphinic acids have been synthesized and complexes of tungsten and manganese were obtained containing the carboranylthiophosphinite ligand.

  DOI：

  10.1007/bf00863933
• 作为产物：
  描述：

  bis(9-o-carboranyl)disulfide 在 盐酸 、 锌 作用下， 以 溶剂黄146 为溶剂， 以80%的产率得到8–mercapto–1,2–dicarba–closo–dodecaborane
  参考文献：
  名称：

  Preparation of BIS(o- and m-carboranyl) disulfides by reaction of sulfur chlorides with o- and m-carboranes in presence of A1C13

  摘要：

  DOI：

  10.1007/bf00963702

文献信息

• Thermal isomerizations of monothiolated carboranes (HS)C 2 B 10 H 11 and the solid-state investigation of 9-(HS)-1,2-C 2 B 10 H 11 and 9-(HS)-1,7-C 2 B 10 H 11
  作者：Tomáš Baše、Jan Macháček、Zuzana Hájková、Jens Langecker、John D. Kennedy、Michael J. Carr

  DOI：10.1016/j.jorganchem.2015.06.020

  日期：2015.12

  B-thiolated isomers 9-(HS)-1,7-C2B10H11 (9-m) and 9-(HS)-1,2-C2B10H11 (9-o) show two types of reaction: first, removal of an SH group from the closo-dicarbadodecaborane skeleton, and second, skeletal isomerizations from ortho to meta to para that lead to new isomers. A previously unreported SH skip from carbon-to-boron is also observed. The effect of the thiol group on the skeletal rearrangement is discussed

  在300〜500℃，三C-硫醇化闭合碳-dicarbadodecaborane异构体1-（HS）-1,2--C 2乙10 ħ 11（1- ø），1-（HS）-1,7--C 2乙10 H 11（1- m）和1-（HS）-1,12-C 2 B 10 H 11（1- p）和两个B-硫代异构体9-（HS）-1,7-C 2 B 10 H 11（9- m）和9-（HS）-1,2-C 2 B 10 H 11（9- o）示出了两种类型的反应组成：首先，从除去SH基团的闭合碳-dicarbadodecaborane骨架，和第二，骨骼异构化从邻位到间位到第导致新的异构体。还观察到以前从未报道过的从碳到硼的SH跳跃。讨论了巯基对骨骼重排的影响。异构化产物是基于其计算获得的偶极矩与其气相色谱保留时间的相关性进行分配的。单硫醇化物质分子能的计算结果表明，所计算的相对稳定性与异构化产物的发生率和相对量之间具有良好的一致性。两种起始的B-硫醇化异构体9
• Fusing Bismuth and Mercaptocarboranes: Design and Biological Evaluation of Low‐Toxicity Antimicrobial Thiolato Complexes
  作者：Christoph Selg、Toni Grell、Alexandra Brakel、Philip C. Andrews、Ralf Hoffmann、Evamarie Hey‐Hawkins

  DOI：10.1002/cplu.202300759

  日期：——

  This study proposes an innovative strategy to enhance the pharmacophore model of antimicrobial bismuth thiolato complex drugs by substituting hydrocarbon ligand structures with boron clusters, particularly icosahedral closo‐dicarbadodecaborane (C₂B₁₀H₁₂, carboranes). The hetero‐ and homoleptic mercaptocarborane complexes BiPh₂L (1) and BiL₃ (2) (L=9‐S‐1,2‐C₂B₁₀H₁₁) were prepared from 9‐mercaptocarborane (HL) and triphenylbismuth. Comprehensive characterization using NMR, IR, MS, and XRD techniques confirmed their successful synthesis. Evaluation of antimicrobial activity in a liquid broth microdilution assay demonstrated micromolar to submicromolar minimum inhibitory concentrations (MIC) suggesting high effectiveness against S. aureus and limited efficacy against E. coli. This study highlights the potential of boron‐containing bismuth complexes as promising antimicrobial agents, especially targeting Gram‐positive bacteria, thus contributing to the advancement of novel therapeutic approaches.

  摘要 本研究提出了一种创新策略，通过用硼簇取代烃配体结构，特别是二十面体闭式二卡硼烷（C2B10H12，硼烷），来增强抗菌铋硫醇络合物药物的药效模型。由 9-巯基硼烷（HL）和三苯基铋制备出了异性和同性巯基硼烷配合物 BiPh2L (1) 和 BiL3 (2)（L=9-S-1,2-C2B10H11）。利用 NMR、IR、MS 和 XRD 技术进行的综合表征证实了它们的成功合成。在液体肉汤微量稀释法中进行的抗菌活性评估显示，其最低抑菌浓度（MIC）从微摩尔到亚摩尔不等，这表明其对金黄色葡萄球菌具有很高的效力，而对大肠杆菌的效力有限。这项研究强调了含硼铋复合物作为有前景的抗菌剂的潜力，尤其是针对革兰氏阳性细菌，从而有助于新型治疗方法的发展。
• B‐Mercaptocarboranes: A New Synthetic Route
  作者：Kuanysh Z. Kabytaev、Thomas A. Everett、Alexander V. Safronov、Yulia V. Sevryugina、Satish S. Jalisatgi、M. Frederick Hawthorne

  DOI：10.1002/ejic.201201518

  日期：2013.5.6

  AbstractA novel route for synthesis of B‐mercaptocarboranes is described. The reaction proceeds through Pd‐catalyzed iodine exchange with the sulfur nucleophile TIPS–SH in mono‐ and diiodinated ortho‐, meta‐, and para‐carboranes. Self‐assembled monolayers of selected B‐mercaptocarboranes on a gold surface were analyzed by X‐ray photoelectron spectroscopy and their water contact angles were assessed.