9,12-diiodo-1,2-dicarba-closo-dodecarborane(12) | 17702-35-1

• 英文名称: 9,12-diiodo-1,2-dicarba-closo-dodecarborane(12)
• 英文别名: 9,12-diiodo-1,2-dicarba-closo-dodecaborane；9,12-diiodo-ortho-carborane；9,12-B-diiodo-o-carborane；9,12-diiodo-1,2-carborane；9,12-diiodo-o-carborane；9,12-I2-1,2-carborane
• CAS: 17702-35-1
• 化学式: C₂H₁₀B₁₀I₂
• 分子量: 396.02
• InChiKey: FZOPZLMDAHYNMN-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C(Solv: hexane (110-54-3))

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：

  9,12-diiodo-1,2-dicarba-closo-dodecarborane(12) 在 trans-bis(triphenylphosphine)palladium dichloride 4-bromoacetophenone ethylene ketal 、 CH₃MgBr 、 Mg 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以54%的产率得到9,12-bis(4-acetylphenyl)-1,2-dicarbadodecaborane(12)
  参考文献：
  名称：

  Synthesis and Crystal Structure of 9,12-Bis-(4-acetylphenyl)-1,2-dicarbadodecaborane(12):  Self-Assembly Involving Intermolecular Carboranyl C−H Hydrogen Bonding

  摘要：

  DOI：

  10.1021/ja9803411
• 作为产物：
  描述：

  (η2-9,12-I2-1,2-C2B10H9)Ni(PPh3)2 以 四氢呋喃 为溶剂， 生成 9,12-diiodo-1,2-dicarba-closo-dodecarborane(12)
  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

• Synthesis of Globular Precursors
  作者：Francesc Teixidor、Reijo Sillanpää、Ariadna Pepiol、Marius Lupu、Clara Viñas

  DOI：10.1002/chem.201501223

  日期：2015.9.1

  produce new dendritic or dendrimer‐like structures. Polyanionic species were obtained in high yield through the ring‐opening reaction of cyclic oxonium compound [3,3′‐Co(8‐C4H8O2‐1,2‐C2B9H10)(1′,2′‐C2B9H11)] by using terminal hydroxyl groups as nucleophiles. These new polyanionic compounds that contain multiple metallacarborane clusters at their periphery may prove useful as new classes of compounds

  o-碳硼烷（C 2 B 10 H 12）适合用作球形大分子，树突或树状聚合物的核心。为达到这一目标，对碳硼烷骨架上末端烯烃基团的精确定义的取代模式进行了Heck交叉偶联反应或氢硼化反应，从而形成了羟基封端的臂。这些导致了新的末端基团（氯，溴和甲苯磺酰基离去基团，有机酸和叠氮化物），使酯的产生，点击化学反应和氧鎓开环能够作为反应的例子进行展示，这些反应证明了球形二十面体的广泛可能性碳硼烷产生新的树枝状或树状大分子结构。通过环状氧鎓化合物[3,3'-Co（8-C 4 H 8 O2 1,2，C 2 B 9 H 10）（1'，2'C 2 B 9 H 11）]，使用末端羟基作为亲核试剂。这些新的在周围含有多个金属碳硼烷簇的聚阴离子化合物可能被证明是用于水溶性增强的硼中子俘获治疗的新型化合物，也可以作为制造新型高硼球状大分子的核心。
• New Approach to the Synthesis of 3-Alkyl-1,2-dicarba-<i>closo</i>-dodecaboranes: Reaction of Alkyldichloroboranes with Thallium Dicarbollide
  作者：Alexander V. Safronov、Natalia I. Shlyakhtina、M. Frederick Hawthorne

  DOI：10.1021/om201060e

  日期：2012.4.9

  2-dicarba-closo-dodecaboranes were prepared in good yields via the reaction of alkyldichloroboranes, which were generated in situ through hydroboration of the corresponding alkenes with a dichloroborane–dioxane complex, with thallium dicarbollides in anhydrous dichloromethane at room temperature. This reaction also affords insertion products with new thallium dicarbollides prepared from 3-iodo- and 9-iodo-1,2-dic

  许多3-烷基取代的1,2- dicarba-闭合碳-dodecaboranes经由alkyldichloroboranes的反应，其产生了良好的收率制备原位与通过相应的烯烃的硼氢化一个二氯硼二恶烷络合物，铊dicarbollides在室温下用无水二氯甲烷洗脱。该反应还得到插入产品具有新铊dicarbollides从3-碘和9-碘代-1,2- dicarba-制备闭合碳-dodecaboranes。将合成的3-烷基-1,2- dicarba-闭合碳-dodecaboranes可以在B（6）原子被选择性地脱硼，以形成阴离子的3-烷基-7,8- dicarba-巢-undecaborates。所有化合物均通过NMR和MS技术表征。
• Improved synthesis of icosahedral carboranes containing exopolyhedral B C and C C bonds
  作者：Kierstyn P. Anderson、Harrison A. Mills、Chantel Mao、Kent O. Kirlikovali、Jonathan C. Axtell、Arnold L. Rheingold、Alexander M. Spokoyny

  DOI：10.1016/j.tet.2018.11.040

  日期：2019.1

  this method is tolerant towards alkyl-based Grignard reagents containing β-hydrogens. Furthermore, a transition metal-free approach to the substitution of carborane C-vertices with (hetero)aryl substrates has been developed under nucleophilic aromatic substitution (SNAr) conditions. The selective substitution of carboranes afforded by these methods holds potential for the rational synthesis of heterofunctionalized

  碳硼烷是富含硼的分子簇，具有电子特性，可通过正交方法进行顶点选择性修饰。我们报告了改进的功能化方法，利用正交化学在碳硼烷的富电子B顶点和贫电子C顶点处实现有效取代。通过使用具有富电子联芳基膦配体的钯基预催化剂，可以改善使用相应的格氏试剂在烷基和（杂）芳基上形成B顶点的功能，从而缩短了反应时间。重要的是，该方法对含有β-氢的基于烷基的格氏试剂具有耐受性。此外，在亲核芳香族取代（SNAr）条件下，已经开发出一种无过渡金属的方法用（杂）芳基底物取代碳硼烷C顶点。这些方法提供的碳硼烷的选择性取代具有合理合成在硼和碳基顶点上均带有取代基的杂官能化硼簇的潜力。
• Host-Guest Chemistry of a New Class of Macrocyclic Multidentate Lewis Acids Comprised of Carborane-Supported Electrophilic Mercury Centers
  作者：Xiaoguang Yang、Carolyn B. Knobler、Zhiping Zheng、M. Frederick Hawthorne

  DOI：10.1021/ja00095a018

  日期：1994.8

  1; X = I, n = 1 or 2) were synthesized from the reaction of closo-1,2-Li~-l,2-C~B~~H~~ with HgX2 (X = C1, Br, and I) in 70-80% yields. The free host ( 12lmercuracarborand-4 (1) was obtained by the removal of halide ions from 1.1~~- with AgOAc. The molecular structures of l-CILi, (l.Br)z- (benzo( 15)crown-5)3-Liz(H20)2, and l*Iz(AsPh4)2 have been determined from single-crystal X-ray diffraction studies

  描述了包含亲电子汞中心的碳硼烷支持的大环家族的合成和表征。这些化合物是多齿路易斯酸，已被证明可以结合阴离子，例如 C1-、Br、I- 和 closo-BloHlo2- 以及不带电的亲核物质。阴离子复合物((1,2-C2BloH10Hg)&)Li,(l.XnLi,; X = C1, Br, n = 1; X = I, n = 1 or 2)的锂盐由反应合成Closo-1,2-Li~-l,2-C~B~~H~~ 与 HgX2（X = C1、Br 和 I），产率为 70-80%。游离主体(12lmercuracarborand-4(1)是用AgOAc从1.1~~-中去除卤离子得到的。l-CILi,(l.Br)z-(benzo(15)crown-5)的分子结构3-Liz(H2O)2 和 l*Iz(AsPh4)2 已从单晶 X 射线衍射研究中确定。1. ClLi 在四方空间群 P4/mcc 中结晶，a
• Synthesis, structures, and conductivities of salts (BEDT-TTF)[9,9′(12′)-I2-3,3′-Co(1,2-C2B9H10)2] and (TTF)[9,9′,12,12′-I4-3,3′-Co(1,2-C2B9H9)2]
  作者：O. N. Kazheva、G. G. Aleksandrov、A. V. Kravchenko、V. A. Starodub、G. G. Zhigareva、I. B. Sivaev、V. I. Bregadze、L. I. Buravov、L. V. Titov、O. A. D’yachenko

  DOI：10.1007/s11172-010-0216-y

  日期：2010.6

  The radical cation salts of tetrathiafulvalene (TTF) and bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) with iodo derivatives of cobalt bis(dicarbollide), (TTF)[9,9′,12,12′-I4-3,3′-Co(1,2-C2B9H9)2] and (BEDT-TTF)[9,9′(12′)-I2-3,3′-Co(1,2-C2B9H10)2], respectively, were synthesized and their crystal structures were determined. The introduction of iodine atoms into the lower rim of the dicarbollide

  四硫富瓦烯 (TTF) 和双(亚乙基二硫)四硫富瓦烯 (BEDT-TTF) 与双（二碳化物）钴的碘衍生物的自由基阳离子盐，（TTF）[9,9',12,12'-I4-3,3' -Co(1,2-C2B9H9)2] 和 (BEDT-TTF)[9,9'(12')-I2-3,3'-Co(1,2-C2B9H10)2] 分别合成并确定了它们的晶体结构。与基于未取代钴双（二碳化物）的类似盐相比，将碘原子引入二碳化物配体的下边缘，与上边缘的取代不同，导致自由基阳离子盐的晶体结构和电导率发生微不足道的变化。 ）。