dichloro-5-methylfurane-2-ylborane | 59074-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: dichloro-5-methylfurane-2-ylborane
• 英文别名: 5-dichloroboryl-2-methylfuran；Dichloro-(5-methylfuran-2-yl)borane；dichloro-(5-methylfuran-2-yl)borane
• CAS: 59074-12-3
• 化学式: C₅H₅BCl₂O
• 分子量: 162.811
• InChiKey: WBSTVMGUAOQAPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dichloro-5-methylfurane-2-ylborane 在 KC₈ 作用下， 以 甲苯 、 苯 为溶剂， 反应 2.33h， 生成 (1,3-dimethylimidazol-2-ylidene)₂B₂(5-methyl-2-furanyl)₂
  参考文献：
  名称：

  BB债券的直接硼氢化：一个温和的策略B的扩散？B债券

  摘要：

  非经典结构的优先形成阻碍了对电子精确硼链的合成访问。现有的几种策略涉及强还原试剂或过渡金属催化剂，两者都有明显的缺点。的新的呋喃基和噻吩基取代diborenes合成被呈现，他们与儿茶酚硼烷（CatBH）直接硼氢化以形成新的电子精确乙沿着乙键以及B 3链。该反应是非对映选择性的，可在温和条件下进行，而无需使用通常在B-B偶联反应中使用的强还原剂或过渡金属催化剂。

  DOI：

  10.1002/anie.201309325
• 作为产物：
  描述：

  2-甲基呋喃 、 [(Ph)ClB(2-N,N-dimethylaminopyridine)][AlCl₄] 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 dichloro-5-methylfurane-2-ylborane
  参考文献：
  名称：

  The carboboration of Me₃Si-substituted alkynes and allenes with boranes and borocations

  摘要：

  ArylBCl₂和含有芳基和乙烯基的硼阳离子通过亲电硼化合成，影响了TMS取代炔烃和烯烃的碳硼化反应。

  DOI：

  10.1039/c5dt03003j

文献信息

• 1-Heteroaromatic-Substituted Tetraphenylboroles: π–π Interactions Between Aromatic and Antiaromatic Rings Through a B–C Bond
  作者：Holger Braunschweig、Alexander Damme、J. Oscar C. Jimenez-Halla、Christian Hörl、Ivo Krummenacher、Thomas Kupfer、Lisa Mailänder、Krzysztof Radacki

  DOI：10.1021/ja309935t

  日期：2012.12.12

  A series of 2,3,4,5-tetraphenylboroles substituted with different aromatic heterocycles (thiophene, furan, pyrrole, and dithiophene) in the 1-position were synthesized and characterized by means of NMR, elemental analysis, and X-ray crystallography. In contrast to known 2,3,4,5-tetraphenylboroles, X-ray diffraction revealed a nearly coplanar arrangement of the aromatic heterocycles and the antiaromatic borole scaffold as a result of pi-conjugation, which could be substantiated by DFT calculations. Furthermore, the 2,2'-dithiophene-bridged bisborole (14) exhibits a large bathochromic shift in the absorption spectrum, demonstrating the exceptional Lewis acidity of the nonannulated borolyl moiety.
• Synthesis of the First Heteroaryl-Substituted Boryl Complexes: Strong Stabilizing Effects of Boron–Aryl π-Conjugation
  作者：Holger Braunschweig、Rian D. Dewhurst、Thomas Kramer

  DOI：10.1021/acs.inorgchem.5b00192

  日期：2015.4.6

  The first examples of heteroarylboryl complexes were prepared and have been found to be unreactive toward a range of strong reductants, strong Lewis bases, and halide-abstraction reagents. The inertness of the complexes is attributed to strong p-conjugation between the p-basic heteroaryl groups and the p-acidic boron atom. This hypothesis is supported by comparison of the structural and spectroscopic properties of the heteroarylboryl complexes with analogous previously reported homoarylboryl complexes, with the former showing greater coplanarity of the aryl ring with the boron atom and much less facile reactivity.