2-iodo-closo-1,12-dodecaborane | 22784-33-4

• 英文名称: 2-iodo-closo-1,12-dodecaborane
• 英文别名: 2-iodo-1,12-dicarba-closo-dodecaborane；2-iodo-1,12-dicarbadodecaborane；2-iodo-closo-p-carborane；closo-2-I-1,12-C2B10H11；2-iodo-p-carborane；2-I-p-HCB10H9CH
• CAS: 22784-33-4
• 化学式: C₂H₁₁B₁₀I
• 分子量: 270.124
• InChiKey: VABRIGUFSWLCTO-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：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  2-iodo-closo-1,12-dodecaborane 在 t-BuONa 、 Pd(dba)2 、 K₃PO₄ 作用下， 以 1,4-二氧六环 为溶剂， 以0%的产率得到2-hydroxy-1,12-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Palladium-Catalyzed Amination of 2-Iodo-para-carborane

  摘要：

  The palladium-catalyzed Buchwald-Hartwig amination of B-iodocarborane by various azoles and amines is described for the first time. The reactions of 2-iodo-p-carborane with indole, imidazole, benzimidazole, or carbazole in the system Pd(dba)(2)-BINAP-(BuONa)-O-t in dioxane at 100 degrees C gave 2-p-carboranyl derivatives of these azoles in high yields together with 2-hydroxy-p-carborane as a side product. The reactions of 2-iodo-p-carborane with aromatic amines in the same system gave the amination products in 60-70% yields and also were accompanied by the formation of hydroxy derivatives (up to 30% yields). In a special investigation it was shown that the base (BuONa)-O-t was responsible for its formation. The principle possibility of the amination of 2-iodo-p-carborane by morpholine (with 30% yield) as an example of aliphatic amination was shown. The structures of N-(1,12-dicarba-closo-dodecaboran-2-yl)carbazole (1), N-(1,12-dicarba-closo-dodecaboran-2-yl)benzimidazole (2), N-(1,12-dicarba-closo-dodecaboran-2-yl)indole (4), and 2-hydroxy-1,12-dicarba-closo-dodecaborane (5) have been established by X-ray diffraction studies.

  DOI：

  10.1021/om0611756
• 作为产物：
  描述：

  1,12-dicarba-closo-dodecaborane(12) 在 碘 、 silver trifluoroacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 以81%的产率得到2-iodo-closo-1,12-dodecaborane
  参考文献：
  名称：

  Phenyl-2-carboranyliodonium fluoborate

  摘要：

  DOI：

  10.1007/bf00954687

文献信息

• Mercuration ofB(9)-substitutedmeta- andortho-carboranes
  作者：A. Ya. Usyatinsky、K. V. Budkina、P. V. Petrovskii、V. I. Bregadze

  DOI：10.1007/bf00698511

  日期：1995.4

  The mercuration of substituted R2C2B10H9X-9 type carboranes (where R=m-H, X= Cl, Br, I, Me; R=o-H, X=Me) was studied. It was found that mercury atoms add to the boron atoms in position 10 ofmeta-carboranes and in position 12 ofortho-carboranes,i.e., to the boron atoms adjacent to the boron atom bonded to the X substituent. Symmetrical (R2C2B10H8X)2Hg type derivatives were obtained. It was shown that

  研究了取代的 R2C2B10H9X-9 型碳硼烷（其中 R=mH，X=Cl、Br、I、Me；R=oH，X=Me）的汞化。发现汞原子加到间碳硼烷的10位和邻位碳硼烷的12位的硼原子上，即加到与与X取代基键合的硼原子相邻的硼原子上。获得了对称的 (R2C2B10H8X)2Hg 型衍生物。结果表明，它们可用作金属转移反应的起始原料。
• Synthesis of B-organo-substituted 1,2-, 1,7-, and 1,12-dicarbaclosododecarboranes(12)
  作者：L.I. Zakharkin、A.I. Kovredov、V.A. Ol'shevskaya、Zh.S. Shaugumbekova

  DOI：10.1016/s0022-328x(00)83405-1

  日期：1982.3

  A convenient new method is proposed for the synthesis of 9-organo-substituted o- and m-carboranes and 2-organo-substituted p-carborane by the substitution of iodine in 9-iodine-o-, 9-iodine-m-, and 2-iodine-p-carboranes by an organic group from an organomagnesium compound in the presence of catalytic amounts of phosphine complexes of palladium. For the first time the halogen in boron halogen carboranes

  提出了一种用于合成的方便的新方法9-有机取代的ø -和米-carboranes和2-有机取代p通过碘的9-碘取代-carborane ø - ，9-碘米- ， -在催化量的钯膦配合物存在下，由有机镁化合物中的有机基团生成2-碘-对-氨基甲酸酯。硼卤素碳硼烷中的卤素首次被有机基团取代。
• Dicarba‐ <i>closo</i> ‐dodecaboranes with One and Two Ethynyl Groups Bonded to Boron
  作者：Alexander Himmelspach、Maik Finze

  DOI：10.1002/ejic.201000064

  日期：2010.5

  7-C2B10H10 (3a) were obtained by Pd-catalyzed Kumada-type cross-coupling reactions of the corresponding diiodinated dicarba-closo-dodecaboranes withMe3SiCCMgBr followed by desilylation of the trimethylsilylalkynyl-substituted clusters. In addition, the related closo-C2B10} derivatives with one ethynyl group 1,2-R-9-HCC-closo-1,2-C2B10H9 [R = H (4a), Me (5a)], 9-HCC-closo-1,7-C2B10H11 (6a), and 2-HCC-closo-1

  二乙炔基二卡巴-closo-dodecaboranes 1,2-R2-9,12-(HCC)2-closo-1,2-C2B10H8 [R = H (1a), Me (2a)] 和 9,10-(HCC)2 -closo-1,7-C2B10H10 (3a) 是通过 Pd 催化的 Kumada 型交叉偶联反应获得的，相应的二碘化二羰基-十二碳硼烷与 Me3SiCCMgBr，然后是三甲基甲硅烷基炔基取代的簇的脱甲硅烷基化反应。此外，相关的closo-C2B10}衍生物具有一个乙炔基1,2-R-9-HCC-closo-1,2-C2B10H9 [R = H (4a), Me (5a)], 9-HCC-合成了 closo-1,7-C2B10H11 (6a) 和 2-HCC-closo-1,12-C2B10H11 (7a)，并将它们的光谱特性与二乙炔基取代的 closo-C2B10} 簇的光谱特性进行了比较。通过元素分析、质谱以及多核
• Design and synthesis of iodocarborane-containing ligands with high affinity and selectivity toward ERβ
  作者：Kiminori Ohta、Takumi Ogawa、Yasuyuki Endo

  DOI：10.1016/j.bmcl.2017.07.053

  日期：2017.9

  The selectivity and the binding affinity of previously reported carborane-containing ligands 2 and 3 toward ERβ remains to be optimized. To improve their biological profiles, a series of iodinated carboranyl phenol derivatives (4–6) were designed and synthesized as prospective ERβ-selective ligands with high affinity. Several iodinated carboranyl phenols showed high relative binding affinity (RBA)

  先前报道的含碳硼烷的配体2和3对ERβ的选择性和结合亲和力仍有待优化。为了改善它们的生物学概况，一系列碘化碳硼烷基苯酚衍生物的（4 - 6）被设计并作为具有高亲和力前瞻性ERβ选择性配体合成。由于碘原子与ERβ配体结合域的疏水性氨基酸残基的适当疏水相互作用，几种碘化碳硼烷基苯酚对两个ER，尤其是ERβ均显示出较高的相对结合亲和力（RBA）值。在这些衍生物中，9,10-二碘-间-甲碳烷5f 在MCF-7细胞增殖试验中，RBA对ERβ的值增加了100％以上，对ERβ的选择性比ERα增加了14倍，并且ER激动活性。
• Synthesis of σ-(o-carboran-9-yl)- and σ-(m-carboran-9-yl)-π-cyclopentadienyldicarbonyliron and their rearrangement in reactions with bromine to π-(o-carboran-9-yl)cyclopentadienyl- and π-(m-carboran-9-yl)cyclopentadienyl-dicarbonylironbromides, respectively
  作者：L.I. Zakharkin、A.I. Kovredov、V.A. Olshevskaya、V.A. Antonovich

  DOI：10.1016/0022-328x(84)80161-8

  日期：1984.5

  with bromine, undergo rearrangement with the cleavage of the BFe σ-bond, involving migration of the 9-o- and 9-m-carboranyl groups into the cyclopentadienyl ring, to give π-(o-carboran-9-yl)cyclopentadienyl- and π-(m-carboran-9-yl)cyclopentadienyl-dicarbonyliron bromides, respectively. A simple method to obtain these acids by the oxidation of 9-alkyl-o- and 9-alkyl-m-carboranes with CrO3 in CH3COOH

  9- o-和9- m-碳硼烷基羧酸用于合成σ-（o-碳硼烷-9-基）-和σ-（m-碳硼烷-9-基）-π-环戊二烯基二羰基铁。后者的复合物，在与溴反应，经历重排与BFeσ键的裂解，涉及9-迁移ö -和9-米-carboranyl基团引入环戊二烯基环，得到π-（ø -碳硼烷-9-基）环戊二烯基和π-（米-carboran -9-基）环戊二烯基dicarbonyliron溴化物，分别。一个简单的方法由9 -烷基-的氧化，以获得这些酸ø -和9 -烷基-米-carboranes用的CrO 3在CH 3中发现了COOH。