ten-vertex para-carborane | 23653-23-8

• 英文名称: ten-vertex para-carborane
• 英文别名: closo-1,10-dicarbadecaborane；1,10-dicarba-closo-decaborane；1,10-dicarbadecaborane
• CAS: 23653-23-8
• 化学式: C₂H₁₀B₈
• 分子量: 120.589
• InChiKey: ITRHDJHYNIKAFY-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：

  ten-vertex para-carborane 在 sodium hydride 作用下， 以 乙醚 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  Simple Synthesis, Halogenation, and Rearrangement of closo-1,6-C₂B₈H₁₀

  摘要：

  Room-temperature reaction between nido-5,6-C2B8H12 (1) and elemental iodine in the presence of triethylamine in CH2Cl2 gave the closo-1,6-C2B8H10 (2) dicarbaborane in 85% yield. All the electrophilic halogenation reactions of 2 led exclusively to B(8)-substitution to get a series of 8-X-closo-1,6-C2B8H9 (8X-2) derivatives (where X = Cl, Br, and I). Thermal rearrangements of 2 and 8X-2 at similar to 500-600 degrees C produced closo-1,10-C2B8H10 (3) and a series of halo derivatives 2-X-closo-1,10-C2B8H9 (2X-3), respectively. All the compounds isolated have been characterized by multinuclear (B-11, H-1, and C-13) NMR spectroscopy, mass spectrometry, and elemental analyses, and the structure of 8Br-2 was established by X-ray diffraction study.

  DOI：

  10.1021/om500988z
• 作为产物：
  描述：

  {nido-C2B10H12}(2-) 生成 ten-vertex para-carborane
  参考文献：
  名称：

  二碳-氨基-十硼烷(12)的制备与反应

  摘要：

  摘要：B7C2H11(-2) 与 B2H6 反应生成 NaBH4、H2、1,6B8C2H10 和新的 nido-carborane B8C2H12。B8C2H12 的反应包括通过 HCl 氯化、胺加成和热转化为定量产率的 1,6-B8C2H10 和 H2。在 11B nmr 光谱 (80 MHz) 的基础上讨论了拓扑和结构数据。（作者）

  DOI：

  10.1021/ja00734a042

文献信息

• Development of androgen receptor ligands by application of ten-vertex para-carborane as a novel hydrophobic core structure
  作者：Shinya Fujii、Kiminori Ohta、Tokuhito Goto、Akifumi Oda、Hiroyuki Masuno、Yasuyuki Endo、Hiroyuki Kagechika

  DOI：10.1039/c2md00294a

  日期：——

  AR demonstrate that ten-vertex carborane is useful for development of novel bioactive compounds as well as twelve-vertex carboranes that are well known to be versatile pharmacophores. Ten-vertex carborane, which has not previously been applied in the field of medicinal chemistry, appears to have potential as a hydrophobic pharmacophore with characteristic properties.

  我们在这里报告的新型衍生物的设计，合成，雄激素活性和抗雄激素活性hexadecahedral 1,10-dicarba-闭合碳-decaborane，一般称为十顶点对-碳硼烷。合成的化合物对雄激素受体具有非常高的结合亲和力，并且对雄激素依赖性SC-3细胞系具有抗雄激素活性。两种化合物在SC-3分析中也表现出部分激动活性。碳硼烷衍生物与AR的对接研究表明，十个顶点的碳硼烷可用于开发新型生物活性化合物以及十二个顶点的碳硼烷，众所周知，它们是通用的药效基团。十个顶点的碳硼烷（以前未在药物化学领域中应用）似乎具有作为具有特征性的疏水药效团的潜力。
• Stabilization of a highly porous metal–organic framework utilizing a carborane-based linker
  作者：Daniel J. Clingerman、William Morris、Joseph E. Mondloch、Robert D. Kennedy、Amy A. Sarjeant、Charlotte Stern、Joseph T. Hupp、Omar K. Farha、Chad A. Mirkin

  DOI：10.1039/c4cc09212k

  日期：——

  The first tritopic carborane-based linker, H₃BCA (C₁₅B₂₄O₆H₃₀), based on closo-1,10-C₂B₈H₁₀, has been synthesized and incorporated into a metal–organic framework (MOF), NU-700 (Cu₃(BCA)₂).

  基于closo-1,10-C₂B₈H₁₀的第一个三主体碳硼烷基连接物H₃BCA（C₁₅B₂₄O₆H₃₀）已被合成并纳入一种金属-有机框架（MOF），NU-700（Cu₃(BCA)₂）。
• Improved syntheses of bis(ethynyl)-para-carboranes, 1,12-(RCC)2-1,12-C2B10H10 and 1,10-(RCC)2-1,10-C2B8H8 (R=H or Me3Si)
  作者：Mark A. Fox、Thomas E. Baines、David Albesa-Jové、Judith A.K. Howard、Paul J. Low

  DOI：10.1016/j.jorganchem.2006.05.044

  日期：2006.9

  disposition of the chloride and carboranyl substituents across the double bonds. These vinyl carboranes can be converted to bis(ethynyl) carboranes, 1,12-(RCC)2-1,12-C2B10H10 and 1,10-(RCC)2-1,10-C2B8H8 (R = H or Me3Si), easily, and in high yields. These findings provide the most convenient routes to bis(ethynyl) carboranes from the commercially available carboranes, 1,12-C2B10H12 and 1,10-C2B8H10

  铜介导的12顶点和10顶点对位碳硼烷1,12-C 2 B 10 H 12和1,10-C 2 B 8 H 10与反式-1-碘-2-的交叉偶联反应氯乙烯制得双（反-2-氯乙烯）碳硼烷，1,12-（ClCHCH）2 -1,12-C 2 B 10 H 10和1,10-（ClCHCH）2 -1,10 -C 2 B 8 H 8分别具有良好的收率。两种化合物的分子结构均通过X射线晶体学测定，验证了跨双键的氯和碳硼烷基取代基的反式布置。这些乙烯基碳硼烷可以转化为双（乙炔基）碳硼烷1,1,2- （RCC）2 -1,12-C 2 B 10 H 10和1,10-（RCC）2 -1,10-C 2 B 8 H 8（R = H或Me 3 Si），容易获得，并且产率很高。这些发现为迄今报道的从市售的碳硼烷1,12-C 2 B 10 H 12和1,10-C 2 B 8 H 10生成双（乙炔基）碳硼烷提供了最方便的途径。
• Quantitative syntheses of permethylated <i>closo</i>-1,10-R₂C₂B₈Me₈ (R = H, Me) carboranes. Egg-shaped hydrocarbons on the Frontier between inorganic and organic chemistry
  作者：Mario Bakardjiev、Oleg L. Tok、Aleš Růžička、Zdeňka Růžičková、Josef Holub、Drahomír Hnyk、Jindřich Fanfrlík、Bohumil Štíbr

  DOI：10.1039/c8ra06640j

  日期：——

  Electrophilic methylation of the closo-1,10-R2C2B8H8 (1) (R = H or Me) dicarbaboranes at higher temperatures or thermal rearrangement of the 1,6-R2C2B8Me8 (3) compounds at 400–500 °C generated the B-permethylated derivatives closo-1,10-R2C2B8Me8 (2) in quantitative (>95%) yields. The compounds exhibit extreme air stability as a consequence of a rigid, egg shaped hydrocarbon structures incorporating

  closo -1,10-R 2 C 2 B 8 H 8 ( 1 ) (R = H 或 Me) 二碳硼烷在较高温度下的亲电甲基化或 1,6- R 2 C 2 B 8 Me 8 ( 3 ) 化合物在400–500 °C 下以定量(>95%) 产率生成B-全甲基化衍生物近-1,10-R 2 C 2 B 8 Me 8 ( 2 )。由于刚性的蛋形碳氢化合物结构结合了内部 1,10-C 2 B 8碳硼烷核心，这些化合物表现出极高的空气稳定性。
• Ruthenium Complexes of <i>C,C</i>‘-Bis(ethynyl)carboranes:  An Investigation of Electronic Interactions Mediated by Spherical Pseudo-aromatic Spacers
  作者：Mark A. Fox、Rachel L. Roberts、Thomas E. Baines、Boris Le Guennic、Jean-François Halet、František Hartl、Dmitri S. Yufit、David Albesa-Jové、Judith A. K. Howard、Paul J. Low

  DOI：10.1021/ja0779755

  日期：2008.3.1

  to stabilization of the intermediate redox products [4a]+ and [4b]+ through interactions between the metal centers across a distance of ca. 12.5 A. The mono-oxidized bimetallic complexes [4a]+ and [4b]+ exhibit spectroscopic properties consistent with a description of these species in terms of valence-localized (class II) mixed-valence compounds, including a unique low-energy electronic absorption band

  配合物[Ru(1-C[三键]C-1,10-C2B8H9)(dppe)Cp*] (3a), [Ru(1-C[三键]C-1,12-C2B10H11)(dppe) )Cp*] (3b), [Ru(dppe)Cp*}2mu-1,10-(C[三键]C)2-1,10-C2B8H8}] (4a) 和 [Ru( dppe)Cp*}2mu-1,12-(C[triple bond]C)2-1,12-C2B10H10}] (4b)，形成具有代表性的系列单金属和双金属乙炔配合物，具有 10-和已制备并表征了嵌入二乙炔基桥连配体中的 12 顶点碳硼烷。此外，这些化合物已在所有可接近的氧化还原状态下通过光谱（UV-vis-NIR、IR）进行了检查。两者的明显分离，在双金属配合物 4a 和 4b 的循环伏安图中观察到的单电子阳极波在很大程度上与电解质的性质无关，并且归因于中间氧化还原产物 [4a]+ 和 [4b]+