3-methoxy-7-(methoxymethyl)-3-borabicyclo[3,3,1]non-6-ene | 69464-55-7

• 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: 3-methoxy-7-(methoxymethyl)-3-borabicyclo[3,3,1]non-6-ene
• 英文别名: 3-Methoxy-7-(methoxymethyl)-3-borabicyclo[3.3.1]non-6-ene
• CAS: 69464-55-7
• 化学式: C₁₁H₁₉BO₂
• 分子量: 194.082
• InChiKey: ONHJGMWVRFGZND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-7-(methoxymethyl)-3-borabicyclo[3,3,1]non-6-ene 在 十二/十四烷基二甲基氧化胺 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 [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：

  三烯丙基硼烷 反应 3.0h， 生成 3-methoxy-7-(methoxymethyl)-3-borabicyclo[3,3,1]non-6-ene
  参考文献：
  名称：

  基于烯丙基硼-乙炔缩合的7-取代3-氮杂双环[3.3.1]非6-烯的设计

  摘要：

  开发了从可用的 3-硼双环 [3.3.1] 非 6-烯（烯丙基硼 - 乙炔缩合的产物）有效合成 7-取代的 3-氮杂双环 [3.3.1] 非 6-烯。带有含氮取代基的末端炔烃首次参与与三烯丙基硼烷的反应。

  DOI：

  10.1007/s11172-021-3306-0

文献信息

• Compositions and methods for inducing CD81 dependent antiproliferation and for treating hepatitis C and other disorders
  申请人：The Regents of the University of California

  公开号：US20040242542A1

  公开（公告）日：2004-12-02

  Small molecule analogues of 1-aminoadamantane and methods for using such compositions to induce CD81-dependent antiproliferative effects and/or for the treatment of disorders of human or veterinary patients and/or for the manufacture of therapeutic preparations used to treat such disorders.

  1-氨基金刚烷的小分子类似物及使用这种组合物诱导CD81依赖性抗增殖效应和/或用于治疗人类或兽医患者的疾病和/或用于制造用于治疗这些疾病的治疗制剂的方法。
• 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.
• Organoboron compounds
  作者：M. E. Gurskii、B. M. Mikhailov

  DOI：10.1007/bf00953589

  日期：1981.2
• Organoboron compounds. 379. Boron chelates based on 7-methoxymethyl-3-borabicyclo [3.3.1]non-6-ene derivatives
  作者：B. M. Mikhailov、M. E. Kuimova

  DOI：10.1007/bf00950588

  日期：1980.8
• Organoboron compounds. 368. Reaction of triallylborane with propargyl alkyl ethers
  作者：B. M. Mikhailov、T. K. Baryshnikova

  DOI：10.1007/bf00951715

  日期：1979.11