9-hydroxy-m-carborane | 54360-42-8

• 英文名称: 9-hydroxy-m-carborane
• 英文别名: 9-hydroxy-1,7-dicarba-closo-dodecaborane；9-OH-m-C₂B₁₀H₁₁
• CAS: 54360-42-8
• 化学式: C₂H₁₂B₁₀O
• 分子量: 160.227
• InChiKey: UJDQFURVHRTSQD-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-hydroxy-m-carborane 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 9-OCH3-1,7-dicarba-closo-dodecaborane
  参考文献：
  名称：

  B–N, B–O, and B–CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes

  摘要：

  Carboranes are boron-rich molecules that can be functionalized through metal-catalyzed cross coupling. Here, for the first time, we report the use of bromo-carboranes in palladium-catalyzed cross-coupling for efficient B-N, B-O, and unprecedented B-CN bond formation. In many cases bromo-carboranes outperform the traditionally utilized iodo-carborane species. This marked difference in reactivity is leveraged to circumvent multistep functionalization by directly coupling small nucleophiles (-OH,-NH2, and -CN) and multiple functional groups onto the boron-rich clusters.

  DOI：

  10.1021/jacs.6b05505
• 作为产物：
  描述：

  phenyl(m-carboran-9-yl)bromonium tetrafluoroborate 在 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 以73%的产率得到9-hydroxy-m-carborane
  参考文献：
  名称：

  Reactions of bromonium salts of the carboborane series with nucleophiles

  摘要：

  DOI：

  10.1007/bf00953942

文献信息

• B(9)-OH-<i>o</i>-Carboranes: Synthesis, Mechanism, and Property Exploration
  作者：Yan-Na Ma、Huazhan Ren、Yanxuan Wu、Na Li、Feijing Chen、Xuenian Chen

  DOI：10.1021/jacs.2c13570

  日期：——

  Herein, we present a chemically robust and efficient synthesis route for B(9)-OH-o-carboranes by the oxidation of o-carboranes with commercially available 68% HNO3 under the assistance of trifluoromethanesulfonic acid (HOTf) and hexafluoroisopropanol (HFIP). The reaction is highly efficient with a wide scope of carboranes, and the selectivity of B(9)/B(8) is up to 98:2. The success of this transformation

  在此，我们通过在三氟甲磺酸 (HOTf) 和六氟异丙醇 (HFIP) 的协助下使用市售的 68% HNO 3氧化邻碳硼烷，提出了一种化学稳健且高效的 B(9)-OH-o-碳硼烷合成路线. 反应效率高，碳硼烷范围广，B(9)/B(8)的选择性高达98:2。这种转化的成功依赖于 HNO 3的强亲电性和氧化性，通过布朗斯台德酸 HOTf 和溶剂 HFIP 的氢键促进。机理研究表明，邻碳硼烷的氧化涉及 HNO 3的初始亲电攻击到邻碳硼烷的最具负电性的 B(9) 处的氢原子。在这种转化中，B-H键的氢原子是亲核位点，不同于亲电取代反应中硼原子是亲核位点。因此，这是邻碳硼烷在温和条件下的氧化还原反应，其中 N(V) → N(III) 和 H(-I) → H(I)。9-OH- o的衍生化-carborane 进一步检查，carboranyl 基团被成功地引入氨基酸、聚乙二醇、生物素、脱氧尿苷和糖类。毫无
• Deboronation of 9-substituted-ortho- and -meta-carboranes
  作者：Mark A. Fox、Kenneth Wade

  DOI：10.1016/s0022-328x(98)00881-x

  日期：1999.1

  A systematic study has been carried out of deboronation reactions of a series of icosahedral carborane derivatives bearing a variety of substituents on selected (generally antipodal) boron atoms. Reactions of the 9-substituted meta-carboranes, 9-R-1,7-C2B10H11 (R = OH, 4-MeC6H4, F, Cl, Br, I), with tetrabutylammonium fluoride hydrate (TBAFH) in refluxing THF gave nido-carborane salts containing a mixture of 1- and 6-R-7,9-C(2)B(9)H(<(11)over bar>) nido-anions. Regioselective deboronation occurred with the 9-halo-meta-carboranes, 9-X-1,7-C2B10H11 (X = F, Cl, Br, I), producing a 2:1 ratio mixture of nido 6-X-7,9-C(2)B(9)H(<(11)over bar>) and 1-X-7,9-C(2)B(9)H(<(11)over bar>). Calculated Mulliken charges at B2 and B3 of some 9-substituted-meta carboranes show that these vary in line with observed deboronation rates and product ratios in their reactions with TBAFH. The ortho-carborane derivative 9-I-1,2-C2B10H11 and TBAFH gave the tetrabutylammonium salt of the nido anion 5(6)-I-7,8-C(2)B(9)H(<(11)over bar>). The mercurated and thallated meta carboranes, 9-M-1,7-C2B9H11 (M = HgOCOCF3 and Tl(OCOCF3)(2)), with TBAFH underwent boron-metal bond cleavage to yield mainly the nido anion 7,9-C(2)B(9)H(<(12)over bar>). Multinuclear (B-11, C-13, H-1, F-19) NMR spectra of the carboranes have been recorded and assigned. (C) 1999 Elsevier Science S.A. All rights reserved.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.12, 5.2.1, page 220 - 250
  作者：

  DOI：——

  日期：——
• Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P., Inorganic Chemistry, 1991, vol. 30, # 8, p. 1760 - 1765
  作者：Grushin, Vladimir V.、Demkina, Iraida I.、Tolstaya, Tat'yana P.

  DOI：——

  日期：——
• Demkina, I. I.; Grushin, V. V.; Vanchikov, A. N., Journal of general chemistry of the USSR, 1987, vol. 57, p. 1199 - 1205
  作者：Demkina, I. I.、Grushin, V. V.、Vanchikov, A. N.、Tolstaya, T. P.、Orlinkov, A. V.

  DOI：——

  日期：——