3-bromo-o-carborane | 22258-25-9

• 英文名称: 3-bromo-o-carborane
• 英文别名: 3-bromo-1,2-dicarba-closo-dodecarborane；3-bromo-1,2-dicarba-closo-dodecaborane
• CAS: 22258-25-9
• 化学式: C₂H₁₁B₁₀Br
• 分子量: 223.123
• InChiKey: KGBVAEGWCLLRPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
  None
• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  3-bromo-o-carborane 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 以 四氢呋喃 为溶剂， 以92%的产率得到3-bromo-μ-9,10,11-[2′-{1′,3′-[2′′,6′′-iPr2(C6H3)]2-1′,3′-N2C3H2}]BH-7,8-C2B9H11
  参考文献：
  名称：

  的反应ø与空间要求-carboranes Ñ合成和1结构表征： -杂环卡宾1加合物†

  摘要：

  在室温下，邻氨基甲酸酯与1,3-双（2,6-二异丙基苯基）咪唑-2-亚烷基在无水THF中的反应可以制备出高收率的几种Nido -carborane-carbene 1：1：1加合物。X射线单晶分析表明，它们是两性离子盐，由一个五配位的硼原子连接的一个氨基甲硼烷笼和咪唑鎓部分组成。它们对碳烯惰性，但对水分和水分敏感。水，导致形成硼酸酯化产物nido -C 2 B 9离子。这些结果揭示了邻氨基甲酸酯的脱硼反应机理。

  DOI：

  10.1039/c2dt31765f
• 作为产物：
  描述：

  (η2-3-Br-1,2-C2B10H9)Ni(PMe3)2 以 四氢呋喃 为溶剂， 生成 3-bromo-o-carborane
  参考文献：
  名称：

  Synthesis and Structural Characterization of Group 10 Metal−Carboryne Complexes

  摘要：

  A series of group 10 metal-carboryne complexes were prepared from an equimolar reaction of MCl2(PR3)(2) with Li2C2B10H10-nXn (M = Ni, Pd, Pt; X = Br, I, Ph; n = 0, I, 2). They were fully characterized by various spectroscopic techniques, elemental analyses, and X-ray diffraction studies. These complexes have similar solid-state structures, in which the metal atom is bonded to two cage carbon atoms and coordinated to two phosphorus atoms in a planar geometry. The coordinated phosphines are labile and can be replaced by other Lewis bases. The bonding interactions between the metal and the carboryne unit can be described as a resonance hybrid of both the M-C sigma- and M C pi-bonding forms. These complexes can be viewed as 16e species.

  DOI：

  10.1021/om100669x

文献信息

• Regioselective Insertion of Carborynes into Ethereal C−H Bond: Facile Synthesis of α-Carboranylated Ethers
  作者：Sunewang R. Wang、Zaozao Qiu、Zuowei Xie

  DOI：10.1021/ja201126h

  日期：2011.4.20

  Carborynes can exist in two resonance forms, bonding form vs biradical form. The biradical form can be readily generated via the elimination of LiI from 1-iodo-n-lithio-1,n-C(2)B(10)H(10) (n = 2, 7) under UV irradiation. They can undergo α-C-H bond insertion with aliphatic ethers, affording α-carboranylated ethers in excellent regioselectivity at room temperature. This serves as a new methodology for

  碳炔可以两种共振形式存在，键合形式与双自由基形式。通过在紫外线照射下从 1-iodo-n-lithio-1,nC(2)B(10)H(10) (n = 2, 7) 中消除 LiI，可以很容易地生成双自由基形式。它们可以与脂肪族醚进行 α-CH 键插入，从而在室温下以优异的区域选择性提供 α-羰基化醚。这作为产生一系列带有烷氧基单元的官能化碳硼烷的新方法。
• Synthesis and structure of 3-arylazo derivatives of <i>ortho</i>-carborane
  作者：Akim V. Shmalko、Sergei A. Anufriev、Marina Yu. Stogniy、Kyrill Yu. Suponitsky、Igor B. Sivaev

  DOI：10.1039/d0nj02052d

  日期：——

  A series of B-substituted arylazo derivatives of ortho-carborane, 3-XC6H4-NN-1,2-C2B10H11 (X = p-NMe2, p-OMe, o-Me), were synthesized by reaction of its diazonium derivative [3-N2-o-C2B10H11][BF4] with aryl Grignard reagents. The treatment of 3-arylazo-ortho-carboranes with CsF in refluxing ethanol results in their selective decapitation with the formation of the corresponding 3-arylazo-nido-carboranes

  一系列的邻-甲碳烷的B-取代的芳偶氮衍生物3-XC 6 H 4 -N N-1,2-C 2 B 10 H 11（X = p -NMe 2，p -OMe，o -Me），通过其重氮衍生物[3-N 2 - o -C 2 B 10 H 11 ] [BF 4 ]与芳基格氏试剂反应合成。在回流的乙醇中用CsF处理3-芳基偶氮-邻位碳氢化合物会导致其选择性断头并形成相应的3-芳基偶氮-Nido-碳硼烷Cs [3-XC 6 H 4 -N N-7,8-C 2 B 9 H 11 ]。
• [3-N₂-o-C₂B₁₀H₁₁][BF₄]: a useful synthon for multiple cage boron functionalizations of o-carborane
  作者：Da Zhao、Zuowei Xie

  DOI：10.1039/c6sc01566b

  日期：——

  A simple and efficient method for selective cage B(3) multiple functionalization of o-carborane is described. Reaction of [3-N2-o-C2B10H11][BF4] with various kinds of nucleophiles gave a very broad spectrum of cage B(3)-substituted o-carborane derivatives, 3-X-o-C2B10H11 (X = OH, SCN, NH2, NO2, N3, CF3, PO(C6H5)2, etc). This reaction may serve as another efficient [18F]-radiolabeling method of carborane

  描述了一种简单有效的邻碳硼烷选择性笼B(3)多官能化方法。 [3-N 2 - o -C 2 B 10 H 11 ][BF 4 ]与各种亲核试剂反应得到非常广谱的笼型B(3)-取代的邻碳硼烷衍生物，3-X- o - C 2 B 10 H 11 (X = OH、SCN、NH 2 、NO 2 、N 3 、CF 3 、PO(C 6 H 5 ) 2等)。该反应可以作为用于正电子发射断层扫描应用的碳硼烷簇的另一种有效的[ 18 F]-放射性标记方法。
• Formal Insertion of <i>o</i>-Carborynes into Ferrocenyl C–H Bonds: A Simple Access to <i>o</i>-Carboranylferrocenes
  作者：Sunewang Rixin Wang、Zuowei Xie

  DOI：10.1021/om300324n

  日期：2012.6.25

  [1-(η5-C5H4)(3-R-1,2-C2B10H10)]Fe(η5-C5H5) (R = H, Ph, Me, Cl, Br, and I) in 19–44% isolated yields. On the other hand, in addition to the desired C–H bond insertion products [1-(η5-C5H4)(3-X-1,2-C2B10H10)]Fe(η5-C5H5), bis(ferrocenyl)-o-carboranes 1,2-[(η5-C5H5)Fe(η5-C5H4)]2-3-X-1,2-C2B10H9 were isolated from the reactions of 1-I-2-Li-3-X-1,2-C2B10H9 (X = Cl, Br, and I) in 12%, 15%, and 8% yields, respectively

  的插入ø -carborynes（1,2-脱氢ö -carboranes）二茂铁成C-H键进行了说明，提供的官能化二茂铁的制备方法方便Ò -carboranes。碳炔前体1-I-2-Li-9,12-Me 2 -1,2-C 2 B 10 H 8或1-I-2-Li-3-R-1,2-C 2 B的反应10 ħ 9（R = H，PH，Me中，氯，溴，和I）与在80℃下在环己烷2.5当量的二茂铁，得到[1-（η 5 -C 5 H ^ 4）（9,12-ME 2 -1,2-C 2 B 10 H 9）]的Fe（η 5 -C 5 H ^ 5）和[1-（η 5 -C 5 H ^ 4）（3-R-1,2--C 2乙10 ħ 10）]的Fe（η 5 -C 5 H ^ 5）（R = H，Ph，Me，Cl，Br和I），分离产率为19-44％。在另一方面，除了所期望的C-H键插入产品[1-（η 5 -C 5 H ^ 4）（3-X-1
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.12, 5.2.1, page 220 - 250
  作者：

  DOI：——

  日期：——