1-[(4-(2-methoxyphenyl)piperazin-1-yl)methyl]-1,2-dicarba-closo-dodecaborane | 1299472-30-2

• 英文名称: 1-[(4-(2-methoxyphenyl)piperazin-1-yl)methyl]-1,2-dicarba-closo-dodecaborane
• 英文别名: 1-[1-(2-methoxyphenyl)-4-methylpiperazine]-closo-1,2-C2B10H11
• CAS: 1299472-30-2
• 化学式: C₁₄H₂₈B₁₀N₂O
• 分子量: 348.499
• InChiKey: NKLNJOZLVOXODA-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-[(4-(2-methoxyphenyl)piperazin-1-yl)methyl]-1,2-dicarba-closo-dodecaborane 在 NaF 作用下， 以 not given 为溶剂， 生成
  参考文献：
  名称：

  The preparation and characterization of functionalized carboranes and Re/Tc-metallocarboranes as platforms for developing molecular imaging probes: Structural and cage isomerism studies

  摘要：

  A study of the structure and reactivity of a series of carborane ligands [(RC2B9H11)(-)] towards Re(I) and Tc-99m(I) was undertaken in which the arising products [(M(CO)(3)RC2B9H10)(-), M = Re, Tc-99m] can be used as platforms to develop organometallic molecular imaging agents. Synthetic methods are reported that produce good yields of the target ligands and metal complexes where the organometallic complexes were prepared in aqueous solvents at both the macroscopic scale and at the tracer level. NMR and X-ray crystallography studies confirmed the structures of the closo and nido-ligands and demonstrated that the rhenacarborane complexes exist as 3,1,2 and/or 2,1,8 isomers where the product distribution depends upon on the steric bulk and electronic influence of the substituent linked to the carbon atom of the carborane cage. Experiments at the tracer level with Tc-99m(I) demonstrated for one ligand a difference in the ratio of isomers produced and the reactivity of the ligands compared to that for Re(I). Data is also presented to show for the first time that a 3,1,2-technetium carborane forms initially during radiolabeling and then upon heating isomerizes to the more stable 2,1,8 isomer. The comparable process is not observed for rhenium. The log D values for the technetium complexes were also measured and are within the range needed to cross the blood-brain-barrier making the reported compounds viable candidates for imaging key targets in the central nervous system. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.03.017
• 作为产物：
  描述：

  1-(2-甲氧苯基)哌嗪 、 1,2-Dicarbadodecaborane(12), 1-(bromomethyl)- 在 diisopropylethylamine 作用下， 以 四氢呋喃 为溶剂， 以27%的产率得到1-[(4-(2-methoxyphenyl)piperazin-1-yl)methyl]-1,2-dicarba-closo-dodecaborane
  参考文献：
  名称：

  The preparation and characterization of functionalized carboranes and Re/Tc-metallocarboranes as platforms for developing molecular imaging probes: Structural and cage isomerism studies

  摘要：

  A study of the structure and reactivity of a series of carborane ligands [(RC2B9H11)(-)] towards Re(I) and Tc-99m(I) was undertaken in which the arising products [(M(CO)(3)RC2B9H10)(-), M = Re, Tc-99m] can be used as platforms to develop organometallic molecular imaging agents. Synthetic methods are reported that produce good yields of the target ligands and metal complexes where the organometallic complexes were prepared in aqueous solvents at both the macroscopic scale and at the tracer level. NMR and X-ray crystallography studies confirmed the structures of the closo and nido-ligands and demonstrated that the rhenacarborane complexes exist as 3,1,2 and/or 2,1,8 isomers where the product distribution depends upon on the steric bulk and electronic influence of the substituent linked to the carbon atom of the carborane cage. Experiments at the tracer level with Tc-99m(I) demonstrated for one ligand a difference in the ratio of isomers produced and the reactivity of the ligands compared to that for Re(I). Data is also presented to show for the first time that a 3,1,2-technetium carborane forms initially during radiolabeling and then upon heating isomerizes to the more stable 2,1,8 isomer. The comparable process is not observed for rhenium. The log D values for the technetium complexes were also measured and are within the range needed to cross the blood-brain-barrier making the reported compounds viable candidates for imaging key targets in the central nervous system. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.03.017

文献信息

• High Yielding Preparation of Dicarba-<i>closo</i>-dodecaboranes Using a Silver(I) Mediated Dehydrogenative Alkyne-Insertion Reaction
  作者：Antonio Toppino、Afaf R. Genady、Mohamed E. El-Zaria、James Reeve、Fargol Mostofian、Jeff Kent、John F. Valliant

  DOI：10.1021/ic400928v

  日期：2013.8.5

  The synthesis of 1,2-dicarba-closo-dodecaboranes (ortho-carboranes) is often low yielding which is a critical issue given the increasing use of boron clusters in material science and medicinal chemistry. To address this barrier, a series of Cu, Ag, and Au salts were screened to identify compounds that would enhance the yields of ortho-caboranes produced when treating alkynes with B10H12(CH3CN)2. Using

  合成1,2- dicarba-闭合碳-dodecaboranes（邻-carboranes）通常低产其是给定的在材料科学和药物化学越来越多地使用硼簇的一个关键问题。为了解决这一障碍，对一系列的铜，银和金盐进行了筛选，以鉴定出可提高用B 10 H 12（CH 3 CN）2处理炔烃时产生的邻环硼烷的收率的化合物。使用各种官能化的配体，包括单官能团和多官能团的内部和末端炔烃，当以催化量使用AgNO 3时，产率会显着提高。硝酸银3 似乎可以防止在碳硼烷形成之前炔烃的不希望的还原/氢硼化，并且该方法与芳基，卤素，羟基，腈，氨基甲酸酯和羰基官能化的炔烃兼容。