endo-pentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecan-8-ol | 69649-21-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: endo-pentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecan-8-ol
• 英文别名: Pentacyclo[5.4.0.02,6.03,10.05,9]undecan-8-ol
• CAS: 69649-21-4
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: HPPCKQCWRBPJIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  endo-pentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecan-8-ol 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 五环[5.4.0.02,6.03,10.05,9]十一烷-8-酮
  参考文献：
  名称：

  Exploring the Requirements for the Hydrophobic Scaffold and Polar Amine in Inhibitors of M2 from Influenza A Virus

  摘要：

  Inhibitors targeting the influenza A virus M2 (A/M2) proton channel have lost their effectiveness due to widespread resistance. As a first step in the development of new inhibitors that address this problem, we have screened several focused collections of small molecules using two-electrode voltage patch clamp assays (TEVC) on Xenopus laevis oocytes. Diverse head groups and scaffolds of A/M2 inhibitors have been explored. It has been found that not only amine but also hydroxyl, aminooxyl, guanidine, and amidine compounds are active against the A/M2 proton channel. Moreover, the channel is able to accommodate a wide range of structural variation in the apolar scaffold. This study offers information to guide the next generation of A/M2 proton channel inhibitor design.

  DOI：

  10.1021/ml100297w
• 作为产物：
  描述：

  exo-11-bromopentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8-one 在 碘代三甲硅烷 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 7.0h， 生成 endo-pentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecan-8-ol
  参考文献：
  名称：

  Synthesis of 1-substituted 12-oxahexacyclo[7.2.1.02,8.03,7.04,11.06,10]dodecanes and their transformation into pentacyclo[6.3.0.02,6.03,10.05,9]undecane derivatives

  摘要：

  The reaction of nucleophilic reagents (organomagnesium and organosodium compounds containing active methylene groups) with exo-11-bromopentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-one leads to the formation of 1-substituted-12-oxahexacyclo[7.2.1.0(2,8).0(3,7).0(4,11).0(6,10)] dodecanes which can be used in the synthesis of trishomocubane derivatives. It is shown, using the 1-methyl- and 1-phenyl-substituted 12-oxadodecanes, that iodotrimethylsilane readily cleaves the ether bond at C(l). The resulting carbonium ions rearrange to form 1,7,11-trisubstituted pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]-undecanes.

  DOI：

  10.1021/jo00059a039

文献信息

• Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists
  作者：Anna S. Sklyarova、Vladimir N. Rodionov、Christopher G. Parsons、Günter Quack、Peter R. Schreiner、Andrey A. Fokin

  DOI：10.1007/s00044-012-0029-7

  日期：2013.1

  Computational modeling demonstrates that the van-der-Waals surfaces of homocubyl amines are similar to that of the neuroprotector Memantine (R). Utilizing readily available precursors we report the preparation of a series of homological cubylamines, namely pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]undecyl-4-amine (trishomocubyl-4-amine, 2), pentacyclo[5.3.0.0(2,5). 0(3,9).0(4,8)]decyl-10-amine (bishomocubyl-10-amine, 3), pentacyclo[4.3.0.0(2,5).0(3,8).0(4,7)]nonyl-9-amine (homocubyl-9-amine, 4), and pentacyclo[4.2.0.0(2,5).0(3,8).0(4,7)]octyl-1-amine (cubylamine, 5). The hydrochlorides of amines 2-5 show pronounced affinity for the (+) MK-801 channel binding site, and it seems likely that these compounds would act as very fast voltage-dependent NMDA receptor antagonists.
• TOLSTIKOV, G. A.;LERMAN, B. M.;BELOGAEVA, T. A.;SULTANOVA, V. S.;XALILOV,+, ZH. ORGAN. XIMII, 1986, 22, N 4, 781-785
  作者：TOLSTIKOV, G. A.、LERMAN, B. M.、BELOGAEVA, T. A.、SULTANOVA, V. S.、XALILOV,+

  DOI：——

  日期：——
• LERMAN B. M.; GALIN F. Z.; UMANSKAYA L. I.; TOLSTIKOV G. A., ZH. ORGAN. XIMII, 1978, 14, HO 12, 2536-2541
  作者：LERMAN B. M.、 GALIN F. Z.、 UMANSKAYA L. I.、 TOLSTIKOV G. A.

  DOI：——

  日期：——
• Tolstikov, G. A.; Lerman, B. M.; Belogaeva, T. A., Russian Journal of Organic Chemistry, 1986, vol. 22, p. 697 - 700
  作者：Tolstikov, G. A.、Lerman, B. M.、Belogaeva, T. A.、Sultanova, V. S.、Khalilov, L. M.、Panasenko, A. A.

  DOI：——

  日期：——
• Exploring the Requirements for the Hydrophobic Scaffold and Polar Amine in Inhibitors of M2 from Influenza A Virus
  作者：Jun Wang、Chunlong Ma、Victoria Balannik、Lawrence H. Pinto、Robert A. Lamb、William F. DeGrado

  DOI：10.1021/ml100297w

  日期：2011.4.14

  Inhibitors targeting the influenza A virus M2 (A/M2) proton channel have lost their effectiveness due to widespread resistance. As a first step in the development of new inhibitors that address this problem, we have screened several focused collections of small molecules using two-electrode voltage patch clamp assays (TEVC) on Xenopus laevis oocytes. Diverse head groups and scaffolds of A/M2 inhibitors have been explored. It has been found that not only amine but also hydroxyl, aminooxyl, guanidine, and amidine compounds are active against the A/M2 proton channel. Moreover, the channel is able to accommodate a wide range of structural variation in the apolar scaffold. This study offers information to guide the next generation of A/M2 proton channel inhibitor design.