1,2-Et2-1,2-C2B10H10 | 189349-52-8

• 英文名称: 1,2-Et2-1,2-C2B10H10
• 英文别名: 1,2-(Et)2-1,2-C2B10H10；1,2-Et₂-1,2-C₂B₁₀H₁₀
• CAS: 189349-52-8
• 化学式: C₆H₂₀B₁₀
• 分子量: 200.335
• InChiKey: WDRPNZBXAHOSGE-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：

  1,2-Et2-1,2-C2B10H10 以 not given 为溶剂， 以90%的产率得到[HNMe3][nido-7,8-(Et)2-7,8-C2B9H10]
  参考文献：
  名称：

  Vinnas, Clara; Pedrajas, Josefina; Bertran, Josep, Inorganic Chemistry, 1997, vol. 36, p. 2482 - 2486

  摘要：

  DOI：
• 作为产物：
  描述：

  癸硼烷 、 3-己炔 在 Proton Sponge 作用下， 以 甲苯 为溶剂， 以23%的产率得到1,2-Et2-1,2-C2B10H10
  参考文献：
  名称：

  离子液体促进的十硼烷脱氢炔烃插入反应：通往邻氨基甲酸酯的新途径。

  摘要：

  与需要路易斯碱催化剂的常规有机溶剂不同，十硼烷脱氢炔烃插入反应会在带有多种末端和内部炔烃的双相离子-液体/甲苯混合物中快速进行，从而提供了有效的，一步一步的途径来官能化-碳氢化合物1-R-1,2-C2B10H11和1-R-2-R'-1,2-C2B10H10衍生物，包括R = C6H5-（1），C6H13-（2），HC [三键] C- （CH2）5-（3），（1-C2B10H11）-（CH2）5-（4），CH3CH2C（O）OCH2-（5），（C2H5）2NCH2-（6），NC-（CH2）3- （7），3-HC [三键] C-C6H4-（8），（1-C2B10H11）-1,3-C6H4-（9），HC [三键] C-CH2-O-CH2-（10 ）; R，R'＝ C2H5-（11）；R = HOCH 2-，R'= CH 3-（12）；R = BrCH 2-；R′＝ CH 3-（13）； R 3 ＝

  DOI：

  10.1021/ic800999y

文献信息

• Practical Synthesis of B(9)-Halogenated Carboranes with <i>N</i>-Haloamides in Hexafluoroisopropanol
  作者：Wenjing Guo、Chenyang Guo、Yan-Na Ma、Xuenian Chen

  DOI：10.1021/acs.inorgchem.2c00074

  日期：2022.4.4

  The B(9)-H halogenation of o-carborane and m-carborane was achieved with excellent selectivities in hexafluoroisopropanol (HFIP) under simple reaction conditions: single reagent [trichloroisocyanuric acid (TCCA), tribromoisocyanuric acid (TBCA) or N-iodosuccinimide (NIS)], catalyst-free, air-/moisture-tolerant, and convenient work-up. With this method, a variety of 9-halogenated o-carboranes and m-carboranes

  在简单的反应条件下，在六氟异丙醇 (HFIP) 中以优异的选择性实现邻碳硼烷和间碳硼烷的 B(9)-H 卤化：单一试剂 [三氯异氰脲酸 (TCCA)、三溴异氰脲酸 (TBCA) 或N-碘代琥珀酰亚胺 ( NIS)]，无催化剂，耐空气/耐湿，后处理方便。采用这种方法，得到了多种 9-卤代邻碳硼烷和间碳硼烷，其产率从良好到优异，具有广泛的官能团耐受性。
• Palladium-Catalyzed Regioselective B(9)-Amination of <i>o</i>-Carboranes and <i>m</i>-Carboranes in HFIP with Broad Nitrogen Sources
  作者：Yan-Na Ma、Yan Gao、Yubin Ma、Yan Wang、Huazhan Ren、Xuenian Chen

  DOI：10.1021/jacs.2c03031

  日期：2022.5.11

  for a highly regioselective formation of a B–N bond by Pd(II)-catalyzed B(9)-H amination of o- and m-carboranes in hexafluoroisopropanol (HFIP) with different nitrogen sources under air atmosphere. The silver salt and HFIP solvent play critical roles in the present protocol. The mechanistic study reveals that the silver salt acts as a Lewis acid to promote the electrophilic palladation step by forming

  碳硼烷的胺化在有机合成和药物合成中具有很好的应用前景。然而，目前用于这种转换的方法存在局限性。在此，我们报告了一种实用的方法，该方法通过 Pd(II) 催化的 B(9)-H 胺化在具有不同氮源的六氟异丙醇 (HFIP) 中的邻碳硼烷和间碳硼烷在空气中形成 B-N 键。气氛。银盐和 HFIP 溶剂在本协议中起着关键作用。机理研究表明，银盐作为路易斯酸通过形成异质双金属活性催化剂 PdAg(OAc) 3来促进亲电钯化步骤。; HFIP的强供氢键能力和低亲核性增强了Pd(II)的亲电能力。相信这些含氮碳硼烷在新药物的合成中具有潜在的重要意义。
• <scp>Visible‐Light‐Promoted Palladium‐Catalyzed Cross‐Coupling</scp> of Iodocarboranes with Disulfides and Phenylselenyl Chloride^†
  作者：Shimeng Li、Yizhen Liu、Zuowei Xie

  DOI：10.1002/cjoc.202300481

  日期：2024.1.15

  This work describes a general method for the synthesis of a series of sulfenylated and selenylated carboranes at room temperature using readily available iodocarboranes as starting materials via boron-centered carboranyl radicals. Such hypervalent boron radicals are generated by a visible-light-promoted Pd(0)/Pd(I) pathway. They are useful intermediates and can be trapped by disulfides and phenylselenyl

  这项工作描述了在室温下使用容易获得的碘碳硼烷作为起始原料，通过以硼为中心的碳硼烷基自由基合成一系列磺酰化和硒化碳硼烷的一般方法。这种高价硼自由基是由可见光促进的 Pd(0)/Pd(I) 途径产生的。它们是有用的中间体，可以被二硫化物和苯基硒基氯捕获，以方便构建 B-S/Se 键。
• Synthesis, Structural Characterization, and Reactivity Studies of 5-CF₃SO₃-B₁₀H₁₃
  作者：Emily R. Berkeley、William C. Ewing、Patrick J. Carroll、Larry G. Sneddon

  DOI：10.1021/ic500684b

  日期：2014.5.19

  In contrast to previous reactions carried out in cyclopentane solvent at room temperature that produced 6-TfO-B10H13 (TfO = CF3SO3), the reaction of c/oso-B10H102- with a large excess of trifluoromethanesulfonic acid in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate (bmimOTf) gave exclusively the previously unknown S-TfO-B10H13 isomer. Experimental and computational studies demonstrated that the difference in the products of the two reactions is a result of 6-TfO-B10H13 isomerizing to S-TfO-B10H13 above room temperature in bmimOTf solutions. Reactivity studies showed that 5-TfO-B10H13: (1) is deprotonated by reaction with 1,8-bis(dimethylamino)naphthalene to form the S-TfO-B10H121- anion; (2) reacts with alcohols to produce 6-RO-B10H13 boryl ethers (R = Me and 4-CH3O-C6H4); (3) undergoes olefin-hydroboration reactions to form 5-TfO-6,9-R-2-B10H11 derivatives; and (4) forms a 5-TfO-6,9-(Me2S)(2)-B10H11 adduct at its Lewis acidic 6,9-borons upon reaction with dimethylsulfide. The S-TfO-6,9-(Me2S)(2)-B10H11 adduct was also found to undergo alkyne-insertion reactions to form a range of previously unreported triflate-substituted 4-TfO-ortho-carboranes (1-R-4-TfO-1,2-C2B10H10) and reactions with triethylamine or ammonia to form the first TfO-substituted decaborate [R3NH+](2)[2-TfO-B10H92-], and [R3NH+](2)[1-TfO-B10H92-] (R = H, Et) salts.