1-(bromoethyl)-1,2-dicarba-closo-dodecaborane | 24035-02-7

• 英文名称: 1-(bromoethyl)-1,2-dicarba-closo-dodecaborane
• 英文别名: 1-bromoethyl-1,2-dicarba-closo-dodecaborane；1-(o-carboranyl)-2-bromoethane；1-bromoethyl-o-carborane
• CAS: 24035-02-7
• 化学式: C₄H₁₅B₁₀Br
• 分子量: 251.177
• InChiKey: QJWNBOJPDJIGFU-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：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  1-(bromoethyl)-1,2-dicarba-closo-dodecaborane 、 异丙基溴化镁 在 三苯基膦 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以95%的产率得到1-(3-methyl-1-butyl)-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  Copper-catalyzed cross-coupling of 1-haloalkyl -o- carboranes with Grignard reagents: an efficient route to monosubstituted o- carborane derivatives

  摘要：

  A convenient and efficient copper-catalyzed reaction has been developed for the synthesis of functionalized o-carborane derivatives by using a Cu/phosphine catalytic system. Cross-coupling of readily available 1-haloalkyl-o-carboranes with Grignard reagents proceeds efficiently under mild conditions, and the corresponding monosubstituted o-carboranes were obtained in good to excellent yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.019
• 作为产物：
  描述：

  1-(2-hydroxyethyl)-1,2-dicarba-closo-dodecaborane 在 PBr₃ 作用下， 以 neat (no solvent) 为溶剂， 以69%的产率得到1-(bromoethyl)-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  L'Esperance, Robert P.; Li, Zhen-Hong; Van Engen, Donna, Inorganic Chemistry, 1989, vol. 28, # 10, p. 1823 - 1826

  摘要：

  DOI：

文献信息

• Chelating N-heterocyclic carbene–carboranes offer flexible ligand coordination to Ir^III, Rh^III and Ru^II: effect of ligand cyclometallation in catalytic transfer hydrogenation
  作者：Jordan Holmes、Christopher M. Pask、Charlotte E. Willans

  DOI：10.1039/c6dt02079h

  日期：——

  with [IrCp*Cl2]2, [RhCp*Cl2]2 or [Ru(p-cymene)Cl2]2 in the presence of Ag2O to prepare complexes of the type [MCp*(NHC)Cl2] (M = Ir, Rh; NHC = N-heterocyclic carbene) or [Ru(p-cymene)(NHC)Cl2]. When the NHC contained an N-tBu substituent, C–H activation of the tBu and subsequent alkyl coordination was observed at Ir. Coordination of the closo-dicarbadodecaborane moiety to Ir was possible to give 7-membered

  由乙基系链连接的咪唑鎓盐闭合碳-dicarbadodecaboranes与[IRCP *氯2 ] 2，[RHCP *氯2 ] 2或[茹（p -cymene）氯2 ] 2中Ag的存在2 O操作制备[MCa href=https://www.molaid.com/MS_6449 target="_blank">CP *（NHC）Cl 2 ]的配合物（M = Ir，Rh； NHC = N杂环卡宾）或[Ru（对-cymene）（NHC）Cl 2 ]。当NHC包含一个N- t Bu取代基时，在Ir处观察到t Bu的CH活化和随后的烷基配位。Closo的协调Ir的-dicarbadodecaborane部分可能产生7元金属环，通过NHC的羧碳与碳硼烷的碳原子或硼原子配位。对苯乙酮转化为1-苯乙醇的加氢反应中Ir配合物的研究表明，碳硼烷部分的环金属化对于催化效率很重要，表明双功能机理和二卡巴十二硼烷阴离子的参与。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.12, 4.7, page 26 - 41
  作者：

  DOI：——

  日期：——
• Davis, A.; Soloway, A. H., Journal of Medicinal Chemistry, 1967, vol. 10, p. 730 - 732
  作者：Davis, A.、Soloway, A. H.

  DOI：——

  日期：——
• Tethered N-Heterocyclic Carbene-Carboranyl Silver Complexes for Cancer Therapy
  作者：Jordan Holmes、Rachel J. Kearsey、Katie A. Paske、Frances N. Singer、Suliman Atallah、Christopher M. Pask、Roger M. Phillips、Charlotte E. Willans

  DOI：10.1021/acs.organomet.9b00228

  日期：2019.6.24

  Silver complexes of tethered N-heterocyclic carbene-carboranyl ligands have been prepared and fully characterized. The first example of silver bonded directly to the cage of o-carborane has been identified in the solid state. The presence of a carboranyl N substituent on the N-heterocyclic carbene significantly enhances the in vitro cytotoxicity of the silver complex against HCT116 p53(+/+) and HCT116 p53(-/-) colon cancer cells in comparison to a phenyl derivative. Conversely, the presence of a carboranyl on the backbone of a xanthine-derived N-heterocyclic carbene decreases the in vitro cytotoxicity of the silver complex in comparison to its phenyl derivative. Stability studies on the xanthine-derived ligands and complexes show that decomposition via deboronation occurs in hydrous dimethyl sulfoxide, which may attribute to the contrasting in vitro behaviors of the carborane-containing complexes.