1-(phthalimidomethyl)-1,2-dicarba-closo-dodecaborane(12) | 31070-98-1

• 英文名称: 1-(phthalimidomethyl)-1,2-dicarba-closo-dodecaborane(12)
• 英文别名: 1-(phthalimidomethyl)-1,2-closo-dodecaborane；N-[(-o-carboran-1-yl)methyl]phthalimide；1-(CH2NCOC6H4CO)-1.2-C2B10H11
• CAS: 31070-98-1
• 化学式: C₁₁H₁₇B₁₀NO₂
• 分子量: 303.371
• InChiKey: UUFHUGMDSVCIKB-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-(phthalimidomethyl)-1,2-dicarba-closo-dodecaborane(12) 在 sodium tetrahydroborate 、 盐酸 作用下， 以 异丙醇 、 水 、 溶剂黄146 为溶剂， 反应 25.0h， 以99%的产率得到1-(aminomethyl)-1,2-closo-dodecaborane hydrochloride
  参考文献：
  名称：

  The role of polycyclic frameworks in modulating P2X7 receptor function

  摘要：

  Herein we describe our recent attempts to target the P2X7 receptor for potential treatment of neurological disorders. This work focusses on different polycycles including carborane, adamantane or cubane, joined by either a cyanoguanidine or an amide linker to phenyl or isoquinoline moieties. We have demonstrated the superiority of the adamantyl moiety over other polycycles in terms of synthetic accessibility and biological (cellular) activity. We have also shown that an amide or cyanoguanidine linker can greatly alter the biological activity of compounds. This SAR study provides important insights into the types of functionality required to target the P2X7 receptor. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.10.075
• 作为产物：
  描述：

  decaborane, bis(acetonitrile) complex 、 N-丙炔基邻苯二甲酸胺 生成 1-(phthalimidomethyl)-1,2-dicarba-closo-dodecaborane(12)
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.12, 4.7, page 26 - 41

  摘要：

  DOI：

文献信息

• High Yielding Synthesis of Carboranes Under Mild Reaction Conditions Using a Homogeneous Silver(I) Catalyst: Direct Evidence of a Bimetallic Intermediate
  作者：Mohamed E. El‐Zaria、Kunal Keskar、Afaf R. Genady、Joseph A. Ioppolo、James McNulty、John F. Valliant

  DOI：10.1002/anie.201311012

  日期：2014.5.12

  Methods used to prepare functionalized carboranes generally require heating to high temperatures, and thus limits the range of derivatives which can be prepared directly from alkynes. We show here that by using a homogeneous silver(I) catalyst it is now possible to prepare carboranes in good to excellent yield at temperatures below 40 °C, including at room temperature. The process is general and provides

  用于制备官能化碳硼烷的方法通常需要加热至高温，因此限制了可以直接从炔烃制备的衍生物的范围。我们在此表明​​，通过使用均相的银（I）催化剂，现在可以在低于40°C的温度（包括室温）下以良好至极好的收率制备碳硼烷。该过程是常规过程，为功能化硼团簇的制备提供了重要的新合成策略。
• One-pot synthesis of an indole-substituted 7,8-dicarba-nido-dodecahydroundecaborate(−1)
  作者：W. Neumann、R. Frank、E. Hey-Hawkins

  DOI：10.1039/c4dt03218g

  日期：——

  Carbaboranes are increasingly used as pharmacophores to replace phenyl substituents in established drug molecules. In contrast to traditional organic chemistry, elaborate procedures to introduce functionality frequently fail in the case of carbaboranes and their chemistry is often hampered by degradation of the cluster. Herein, the development of a one-pot synthesis of a water-soluble N-nido-dicarbaborato

  甲碳硼烷越来越多地用作药效基团，以取代已建立的药物分子中的苯基取代基。与传统的有机化学相反，在氨基甲酸酯类的情况下，引入功能的复杂程序经常失败，并且它们的化学成分经常因簇的降解而受阻。在此，提出了一种锅法合成水溶性N-nido- dicarbaborato吲哚的方法，包括提出的反应顺序机理。这些研究为结合两种重要的药效团吲哚和咔唑酮提供了有用的合成工具。
• The first carborane triflates: synthesis and reactivity of 1-trifluoromethanesulfonylmethyl- and 1,2-bis(trifluoromethanesulfonylmethyl)-o-carborane
  作者：V. N. Kalinin、E. G. Rys、A. A. Tyutyunov、Z. A. Starikova、A. A. Korlyukov、V. A. Ol'shevskaya、D. D. Sung、A. B. Ponomaryov、P. V. Petrovskii、E. Hey-Hawkins

  DOI：10.1039/b417199c

  日期：——

  The first carborane triflates, namely, 1-trifluoromethanesulfonylmethyl-o-carborane (2) and 1,2-bis(trifluoromethanesulfonylmethyl)-o-carborane (7), were obtained in high yields in the reactions of 1-hydroxymethyl-o-carborane (1) or 1,2-bis(hydroxymethyl)-o-carborane (6) with triflic anhydride (Tf2O) in CH2Cl2 in the presence of pyridine. When an excess of pyridine is employed, 1-o-carboranylmethylpyridinium

  首先 碳硼烷三氟甲磺酸酯，即，1- trifluoromethanesulfonylmethyl- Ö -carborane（2）和1,2-双（trifluoromethanesulfonylmethyl） - Ö -carborane（7），以高收率得到在1羟甲基的反应Ô -carborane（1）或1,2-双（羟甲基）-邻-碳硼烷（6）与三氟甲酸酐（Tf 2 O）在CH 2 Cl 2中的存在下吡啶。当过量吡啶采用，1- ö -carboranylmethylpyridinium三氟甲磺酸酯（3），其保持闭合碳-icosahedral结构，或吡啶鎓盐（4）从1获得具有两性离子的nido- dicarbaundecaboate阴离子，而nido化合物8由6形成。化合物2或7与过量的反应吡啶也分别给了3或8。化合物2被证明是一种方便的碳硼烷基甲基化剂，可与亲核试剂反应（例如，邻苯二甲酰亚胺钾，PPH
• Carborane–β-cyclodextrin complexes as a supramolecular connector for bioactive surfaces
  作者：P. Neirynck、J. Schimer、P. Jonkheijm、L.-G. Milroy、P. Cigler、L. Brunsveld

  DOI：10.1039/c4tb01489h

  日期：——

  The supramolecular carborane–β-cyclodextrin system allows for effective monovalent immobilization of biologically active peptides resulting in efficient cell adhesion and spreading.

  超分子碳硼烷-β-环糊精系统可实现生物活性肽的单价固定，从而实现高效的细胞黏附和扩展。
• Wilson, J. Gerald; Anisuzzaman; Alam, Inorganic Chemistry, 1992, vol. 31, # 10, p. 1955 - 1958
  作者：Wilson, J. Gerald、Anisuzzaman、Alam、Soloway

  DOI：——

  日期：——