9–mercapto–1,2–dicarba–closo–dodecaborane | 64493-43-2

• 英文名称: 9–mercapto–1,2–dicarba–closo–dodecaborane
• 英文别名: ortho-9-mercapto-dicarba-closo-dodecaborane；1,2-dicarbo-close-dodecaborane(12)-9-thiol；9-mercapto-1,2-dicarba-closo-dodecaborane；9-mercapto-o-carborane；o-carborane-9-thiol
• CAS: 64493-43-2
• 化学式: C₂H₁₂B₁₀S
• 分子量: 176.293
• InChiKey: WQIYCEARBFWVFO-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：

  9–mercapto–1,2–dicarba–closo–dodecaborane 在 氯 作用下， 以 二氯甲烷 为溶剂， 生成 9-o-carboranyl sulfenylchloride
  参考文献：
  名称：

  Some transformations of 9-m-carboranylthiol

  摘要：

  DOI：

  10.1007/bf00951070
• 作为产物：
  描述：

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

  Zakharkin, L. I.; Pisareva, I. V., Phosphorus and Sulfur and the Related Elements, 1984, vol. 20, p. 357 - 370

  摘要：

  DOI：

文献信息

• Reactions of 1,2,4,5-tetrazines with S-nucleophiles
  作者：S. G. Tolshchina、R. I. Ishmetova、N. K. Ignatenko、A. V. Korotina、I. N. Ganebnykh、V. A. Ol’shevskaya、V. N. Kalinin、G. L. Rusinov

  DOI：10.1007/s11172-011-0155-2

  日期：2011.5

  The reactions of 3,6-disubstituted and azoloannulated 1,2,4,5-tetrazines containing heterocyclic leaving groups with S-nucleophiles were studied. The methods of introduction of functionalized thiols, including thiol derivatives of 1,7- and 1,2-dicarba-closo-dodecaboranes, into the tetrazine ring were developed. It was established for the first time that, instead of replacement of a leaving group in the tetrazine ring, the attack of S-nucleophile at the unsubstituted carbon atom occurs in the case of imidazo[1,2-b][1,2,4,5]tetrazines to form previously unknown products of nucleophilic substitution of the hydrogen atom.

  研究了含有杂环离去基团的3,6-二取代和含氮唑并环的1,2,4,5-四嗪与S-亲核试剂的反应。开发了将功能化硫醇（包括1,7-和1,2-二碳硼烷硫醇衍生物）引入四嗪环的方法。首次证实，在咪唑并[1,2-b][1,2,4,5]四嗪的情况下，S-亲核试剂不是取代四嗪环中的离去基团，而是攻击未取代的碳原子，形成先前未知的氢原子亲核取代产物。
• Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions
  作者：Valentina A. Ol'shevskaya、Victoria M. Alpatova、Anton V. Makarenkov、Elena G. Kononova、Alexander F. Smol’yakov、Alexander S. Peregudov、Evgeny G. Rys

  DOI：10.1039/d1nj02499j

  日期：——

  Carborane maleimides were prepared in good yields through the thermal cyclization of maleamic acids prepared by the reaction of 3-amino-o-carborane with maleic or 3-bromomaleic anhydrides, respectively. The selective reactivity of synthesized maleimides towards S-nucleophiles was demonstrated. As a result a series of boronated thiosuccinimide- or thiomaleimide-substituted compounds including boron

  以良好的收率制备通过的马来酰胺酸的热环化硼烷马来酰亚胺制备的3-氨基反应ö分别-carborane与马来或3-溴代酸酐，。证明了合成的马来酰亚胺对S-亲核试剂的选择性反应性。结果获得并充分表征了一系列硼化硫代琥珀酰亚胺或硫代马来酰亚胺取代的化合物，包括富含硼的化合物。此外，随着替代模式发生变异的机会可能会导致潜在的生物应用候选物的开发或新材料的开发。
• Chiral carborane-derived thiophosphites: A new generation of ligands for Rh-catalyzed asymmetric hydrogenation
  作者：Sergey E. Lyubimov、Vadim A. Davankov、Pavel V. Petrovskii、Evamarie Hey-Hawkins、Andrey A. Tyutyunov、Evgeny G. Rys、Valery N. Kalinin

  DOI：10.1016/j.jorganchem.2008.09.032

  日期：2008.12

  A new class of chiral monodentate ligands – carborane-containing thiophosphites have been synthesized and tested in the Rh-catalyzed asymmetric hydrogenation of prochiral olefins with the result of up to 99% ee. The dependence of the enantioselectivity on the electronic properties of the carboranyl substituent has been studied.

  合成了一类新型的手性单齿配体-含碳硼烷的硫代亚磷酸酯，并在Rh催化的前手性烯烃的不对称氢化中进行了测试，结果ee高达99％。已经研究了对映选择性对碳硼烷基取代基的电子性质的依赖性。
• 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
• Synthesis and antitumor activity of novel tetrakis[4-(closo-carboranylthio)tetrafluorophenyl]porphyrins
  作者：V. A. Ol’shevskaya、A. V. Zaitsev、V. N. Kalinin、A. A. Shtil

  DOI：10.1007/s11172-014-0751-z

  日期：2014.10

  Novel neutral and anionic fluorinated carboranylporphyrins for boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) were synthesized by the reaction of 5,10,15,20-pentafluorophenylporphyrin and its copper(II), zinc(II), and palladium(II) complexes with closo-mercaptocarboranes and cesium 1-mercapto-1-carba-closo-dodecaborate. Preliminary evaluation of biological activity reveals that anionic carboranylporphyrins are promising agents for BNCT and PDT.

  通过5,10,15,20-五氟苯基卟啉及其铜（II）、锌（II）和钯（II）配合物与闭式硫醇硼烷和1-巯基-1-羰基-闭式十二硼酸铯的反应，合成了用于硼中子俘获疗法（BNCT）和光动力疗法（PDT）的新型中性阴离子氟化碳硼烷卟啉。初步的生物活性评估表明，阴离子碳硼烷卟啉有望成为BNCT和PDT的药剂。