1-boraadamantane-tetrahydrofurane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 1-boraadamantane-tetrahydrofurane
• 英文别名: 1-boraadamantane tetrahydofuran；1-boraadamantane THF complex；1-boraadamantane THF；1-bora-adamantane; compound with tetrahydrofuran (1:1)；1-boratricyclo[3.3.1.13,7]decane;oxolane
• 化学式: C₄H₈O*C₉H₁₅B
• 分子量: 206.136
• InChiKey: TVVSMVZIFLAWHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-boraadamantane-tetrahydrofurane 在 十二/十四烷基二甲基氧化胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以76%的产率得到[3,5-bis(hydroxymethyl)cyclohexyl]methanol
  参考文献：
  名称：

  1-硼金刚烷的多同系化：绘制传播的大三环三烷基硼烷的迁移路径

  摘要：

  三烷基和三芳基有机硼烷在与二甲基亚砜 (1) 反应后会经历多次重复的同系化。这种多重同系反应或多同系反应在活性反应中产生聚亚甲基。将多同系反应应用于环状和多环有机硼烷可以构建独特的低聚和聚合结构，这些结构不容易通过标准烯烃聚合获得。叶立德 1 对 1-硼金刚烷.THF (2) 的多同系化生成新型大三环三烷基硼烷 (3)。这些大环有机硼烷的氧化生成三臂星形聚亚甲基聚合物 (4)，其中包含一个顺式,顺式-1,3,5-三取代的环己烷核。有趣的是，只有三分之一的引发剂导致产物形成，导致观察到的聚合度比预期高 3 倍。对聚合初始阶段的仔细检查表明，1-硼金刚烷.THF 与 1 当量的 1 反应得到单同系产物。发现随后的同源性在第三、第四和第五次亚甲基插入后包含导致异构三环产物的分支点。在这些同系化阶段，所有繁殖的物质都会产生三环三烷基硼烷笼，其具有倒塌的倒锥形硼中心，对叶立德的反应性显着降低。大约三

  DOI：

  10.1021/ja0361291
• 作为产物：
  描述：

  1-boraadamantane 、 borane tetrahydrofuran 以90%的产率得到
  参考文献：
  名称：

  MIXAJLOV B. M.; BARYSHNIKOVA T. K.; KISELEV V. G.; SHASHKOV A. S., IZV. AN CCCP CEP. XIM., 1979, HO 11, 2544-2551

  摘要：

  DOI：
• 作为试剂：
  描述：

  烯丙基溴化镁 、 、 三烯丙基硼烷 、 甲基炔丙基醚 、 三聚丙烯 在 乙醚 、 三烯丙基硼烷 、 borane tetrahydrofuran 、 四氢呋喃 、 1-boraadamantane-tetrahydrofurane 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 3.83h， 以to yield 2.7 g (60%)的产率得到1-boraadamantane-tetrahydrofurane
  参考文献：
  名称：

  Telechelic polymers containing reactive functional groups

  摘要：

  本发明揭示了具有相同聚合物链末端两个反应性官能团的末端反应性聚合物。这些聚合物可以通过将环硼烷引发剂、至少一种自由基聚合单体和氧气组合形成具有硼烷残基的聚合物段来制备，其中硼烷残基来自环硼烷引发剂的作用; 并将硼烷残基转化为至少两个官能团以形成末端反应性聚合物。

  公开号：

  US07262257B2

文献信息

• A novel method of synthesis of 1-azaadamantane from 1-boraadamantane
  作者：Yu.N. Bubnov、M.E. Gursky、D.G. Pershin

  DOI：10.1016/0022-328x(91)86035-o

  日期：1991.7

  furan complex (XIII) is described. This is based on an intramolecular reaction of organic azides with organoboron compounds. Treatment of the boron cage compound XIII with iodine and an excess of sodium azide followed by oxidation (H2O2, OH−) affords 7α-hydroxymethyl-3-azabicyclo[3.3.1]nonane (VII), cyclization of which leads to I in 40% overall yield. Some new boron cage compounds were also isolated

  描述了一种新颖且方便的方法，其由1-硼烷金刚烷-四氢呋喃配合物（XIII）合成1-氮杂金刚烷（I）。这是基于有机叠氮化物与有机硼化合物的分子内反应。用碘硼笼化合物XIII和过量的叠氮化钠，随后氧化的处理（H 2 ö 2，OH - ），得到7α羟甲基-3-氮杂双环[3.3.1]壬烷（VII），其中环化引线的至我的总产量为40％。还分离了一些新的硼笼化合物，特别重要的是二叠氮硼烷（XIV）。
• Synthesis of 1-Boraadamantaneamine Derivatives with Selective Astrocyte vs C6 Glioma Antiproliferative Activity. A Novel Class of Anti-Hepatitis C Agents with Potential to Bind CD81
  作者：Carl E. Wagner、Michael L. Mohler、Gyong Suk Kang、Duane D. Miller、Eldon E. Geisert、Yu-An Chang、Everly B. Fleischer、Kenneth J. Shea

  DOI：10.1021/jm020326d

  日期：2003.7.1

  A variety of amine complexes with 1-boraadamatane were synthesized and subsequently evaluated for an antiproliferative effect on CD81-enriched cell lines to provide evidence for binding and activation of CD81. CD81 is a member of the tetraspanin family of membrane proteins found in all cell lineages in the liver. CD81 signals for antiproliferation when bound by antibodies. It is known that the HCV-E2 envelope glycoprotein binds to the CD81 protein. While it is unclear whether virus entry into host cells is directly linked to virus attachment via CD81 for HCV, this step in the viral life cycle has recently proven to be an effective point of attack for other viruses including HIV and rhinoviruses. The aim of the current study concerns the synthesis of amantidine analogues by appending primary amines to 1-boraadamantane to evaluate such compounds for CD81-dependent antiproliferation of CD81-enriched cell lines (astrocyte) vs CD81-deficient cell lines (C6 glioma). If the antiproliferative effect of these amantidine analogues proves to be an effect of binding and activating CD81, then these compounds may have the potential to prevent or treat HCV infections. Each compound's potential for preventive and therapeutic activity stems from the compound's potential to block viral attachment, virus-cell fusion, or virus entry into host cells or to counter potential mechanisms of HCV immune evasion. Out of a library of over 500 compounds, including randomly selected small molecules and rationally designed small molecules, only the 1-boraadamantaneamine compounds and structurally similar analogues display a significant antiproliferative effect on the CD81-enriched astrocytes relative to the CD81-deficient cell lines. In fact, 1-boraadamantane.L-phenylalanine methyl ester complex (5), 1-boraadamantane.ethanolamine complex (8), and (S)-2-[(adamantane-1-carbonyl)amino]-3-phenylpropionic acid (15) show a dose-dependent, astrocyte-selective antiproliferative activity in the concentration range 0.1-10 muM. This is consistent with the binding and activation of CD81 and represents a 2-fold improvement compared to the clinically prescribed anti-HCV agent, amantidine, in the same concentration range. Consequently, the 1-boraadamantaneamine derivatives present a promising lead in the development of small molecules with potential to bind to CD81 and treat HCV infections.
• Wiesmann, Reinhard F.; Rademacher, Paul, Chemische Berichte, 1994, vol. 127, # 6, p. 1105 - 1110
  作者：Wiesmann, Reinhard F.、Rademacher, Paul

  DOI：——

  日期：——
• 1-Boraadamantane Blows Its Top, Sometimes. The Mono- and Polyhomologation of 1-Boraadamantane
  作者：Carl E. Wagner、Kenneth J. Shea

  DOI：10.1021/ol0159726

  日期：2001.10.1

  1-Boraadamantane-THF (3) reacts with I equiv of dimethylsulfoxonium methylide (4) to afford a monohomologated product. The polyhomologation of 1-boraadamantane-THF by ylide 4 followed by oxidative cleavage generates star polymethylene polymers incorporating a cyclohexane core. However, only one-third of the initiators lead to product formation, resulting in an observed degree of polymerization three times higher than expected. The polyhomologation of 3 was found to contain branch points after the fourth and fifth methylene insertions. At the branch points, the propagating species either terminate in tricyclic trialkylborane cages with collapsed, pyramidal inverted boron centers that are unreactive toward ylide or they continue in uninterrupted polymerization and eventually result in the formation of giant "tube-like" structures such as 5.
• GURSKIJ, M. E.;PERSHIN, D. G.;BUBNOV, YU. N.;POLYAKOV, A. V.;YANOVSKIJ, A+, METALLOORGAN. XIMIYA, 2,(1989) N, S. 1071-1078
  作者：GURSKIJ, M. E.、PERSHIN, D. G.、BUBNOV, YU. N.、POLYAKOV, A. V.、YANOVSKIJ, A+

  DOI：——

  日期：——