[1-NO-2-Ph-1,2-closo-C2B10H10] | 23939-99-3

• 英文名称: [1-NO-2-Ph-1,2-closo-C2B10H10]
• 英文别名: 1-nitroso-2-phenyl-ortho-carborane；1-phenyl-2-nitroso-ortho-carborane；1-NO-2-C6H5-1.2-C2B10H10；(Ph)(o-carboranyl)(NO)
• CAS: 23939-99-3
• 化学式: C₈H₁₅B₁₀NO
• 分子量: 249.323
• InChiKey: GVOJDOFKPOUDEQ-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：

  盐酸 、 [1-NO-2-Ph-1,2-closo-C2B10H10] 在 tin 作用下， 以 乙二醇二甲醚 为溶剂， 以57%的产率得到1-amino-2-phenyl-ortho-carborane
  参考文献：
  名称：

  Exo-π-bonding to an ortho-carborane hypercarbon atom: systematic icosahedral cage distortions reflected in the structures of the fluoro-, hydroxy- and amino-carboranes, 1-X-2-Ph-1,2-C₂B₁₀H₁₀ (X = F, OH or NH₂) and related anions

  摘要：

  对在第二个笼子超碳原子上具有π给体取代基（F、OH、O⁻、NH₂、NH⁻和CH₂⁻）的苯基邻羧烷衍生物的结构进行了核磁共振、X射线晶体学和计算研究。这些化合物的分子结构，特别是它们的笼C1-C2距离和π给体取代基（OH、NH₂、NH⁻和CH₂⁻）的取向，随着exo π-键合程度的变化表现出显著而系统的差异，这一变化与取代基的π给体特性相应。

  DOI：

  10.1039/b406422d
• 作为产物：
  描述：

  1-苯基-o-蒈硼烷 、 亚硝酰氯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以52.2%的产率得到[1-NO-2-Ph-1,2-closo-C2B10H10]
  参考文献：
  名称：

  发展亚硝基碳烷化学†

  摘要：

  新nitrosocarboranes [1-NO-2-R-1,2-闭合碳-C 2乙10 ħ 10 ] [R = CH 2 Cl（上1），CH 3 OCH 2（2）p -MeC 6 ħ 4（3），SiMe 3（4）和SiMe 2 t Bu（5）]和[1-NO-7-Ph-1,7- closo -C 2 B 10 H 10 ]（6）的合成方法是，使适当的硫代碳烷在乙醚中与NOCl在石油醚中的反应，然后用NaHCO 3水溶液淬灭反应。这些明亮的蓝色化合物在光谱学上进行了表征，在某些情况下，通过使用在衍射仪上从液体样品中原位生长的晶体在晶体学上确定了2和6的结构。在所有情况下，亚硝基键合到碳硼烷作为1E取代基（弯曲C-N-O顺序），并且具有对<几乎没有或没有影响δ 11 B>，加权平均11相对于母体（单取代）碳硼烷的化学位移。单酯和1,1'-二（二亚硝基衍生物米-carborane），化合物7和8分

  DOI：

  10.1039/c5dt04831a

文献信息

• New synthetic and structural studies on nitroso-ortho-carboranes RCB10H10CNO and bis(ortho-carboranyl)amines (RCB10H10C)2NH (R=Ph or Me)
  作者：Mark A. Fox、J.A. Hugh MacBride、Richard J. Peace、William Clegg、Mark R.J. Elsegood、Kenneth Wade

  DOI：10.1016/j.poly.2008.12.014

  日期：2009.3

  Improved procedures are reported for the preparation of nitroso-carboranes RCb degrees NO (Cb degrees = 1,2-C2B10H10; R = Ph, Me at cage carbon C2) in 44-77% yield, and of dicarboranylamines (RCb degrees)(2)NH in 55-65% yield by reactions between the lithio-carboranes, RCb degrees Li and nitrosyl chloride, NOCl, in cold mixtures of diethyl ether and either pentane (for RCb degrees NO) or dimethoxyethane (for (RCb degrees)(2)NH). Deprotonation of the amines by (KOBu)-Bu-t in toluene in the presence of 18-crown-6, (CH2CH2O)(6), affords the salts [K(18-crown-6)](+)[(RCb degrees)(2)N](-), X-ray crystal structures of PhCb degrees NO, (PhCb degrees)(2)NH, (MeCb degrees)(2)NH and [K(18-crown-6)](+)[(PhCb degrees)(2)N](-) are described, and the bonding implications of their cage C center dot center dot center dot C distances (1.68, 1.80, 1.75 and 1.99 angstrom, respectively) are discussed. These species provide further striking examples of the remarkable capacity of the ortho-carborane cage to act as a sensitive indicator of the pi-donor characteristics of ligands attached to its cage carbon atoms. (C) 2008 Elsevier Ltd. All rights reserved.
• Trends in ortho-carboranes 1-X-2-R-1,2-C2B10H10 (R=Ph, Me) bearing an exo-CN-bonded substituent group (X=NO, NNR′ or NHR′′)
  作者：Mark A. Fox、Richard J. Peace、William Clegg、Mark R.J. Elsegood、Kenneth Wade

  DOI：10.1016/j.poly.2009.04.041

  日期：2009.8

  The preparation and crystal structures of four ortho-carboranyl-nitrogen compounds, PhCb degrees N=N(C6H4Me-4) (1), PhCb degrees NHNH(C6H4Me-4) (2), MeCb degrees NHNHPh (3) and PhCb degrees NHOH (4) (Cb degrees = 1,2-C2B10H10; nitrogen groups at cage carbon C1, Ph or Me at C2), the last as a 1,4-dioxane solvate, are reported. Comparisons of their structures with those of other ortho-carboranyl-nitrogen systems studied earlier reveal further correlations between their cage C-C and exo-C-N bond distances and bond orders. Substituent orientations and bond distances (cage C1-C2, exo-C1-N) in RCb degrees NHR '' systems (R = Ph or Me at C2) are consistent with dative pi-bonding from a nitrogen lone pair into the cage carbon p-AO otherwise responsible for cage C1-C2 sigma-bonding. Their C1-C2 bond distances are remarkably sensitive to the planar (sp(2)) or pyramidal (sp(3)) nature of the NHR '' group. The N=O and N=NR' residues in RCb degrees X prefer to be orientated in plane with the cage C1-C2 in contrast to the RCb degrees NHR '' systems. Correlations between their cage C-C and exo-C-N bond distances and the B-11 NMR chemical shifts of their antipodal boron atoms reflect the pi-bonding characteristics of the nitrogen substituent. (C) 2009 Elsevier Ltd. All rights reserved.