anti-11-hydroxypentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8-one | 95464-07-6

• 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: anti-11-hydroxypentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8-one
• 英文别名: 11-hydroxypentacyclo[5.4.0.02,6.03,10.05,9]undecan-8-one；3-Hydroxy-1α(H).3β(H)-pentacyclo<6.2.1.0^2.7.0^4.10.0^5.9>undecanon-(6)
• CAS: 95464-07-6
• 化学式: C₁₁H₁₂O₂
• mdl: MFCD00995047
• 分子量: 176.215
• InChiKey: JNVWBGCXBWEFQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  anti-11-hydroxypentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8-one 在 chromium(VI) oxide 、 溶剂黄146 、 potassium hydroxide 、 肼 作用下， 以 水 、 二乙二醇 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：

  pentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>-undecan-8,11-dione monoethyleneacetal 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 anti-11-hydroxypentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8-one
  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

文献信息

• 五环十一烷二酮（PCUD）单边还原成羟基产 物的合成方法
  申请人：北京理工大学

  公开号：CN105111059B

  公开（公告）日：2017-09-29

  本发明的名称为五环十一烷二酮(PCUD)单边还原成羟基产物的合成方法，即通过钯碳(Pd/C)对PCUD加氢还原得到PCUD的单边还原产物。本发明PCUD单边还原产物的合成工艺由下列条件组成：溶剂体积10mL‑100mL，反应温度15℃‑40℃，时间20h‑30h，氢气压力0.1‑0.12MPa；溶剂优选甲醇、二氯甲烷、乙醇、乙酸乙酯、乙酸乙酯与乙酸的混合物或乙醇与乙酸的混合物；催化剂优选2％‑10％wt的Pd/C；柱层析洗脱剂为石油醚与乙酸乙酯，比例优选2:1至4:1。合成PCUD单边还原产物的方法如下：1)取有机溶剂溶解PCUD，加入钯碳后通入氢气，搅拌反应一段时间后得无色液体；2)过滤除去钯碳，得无色透明液体；3)对无色液体进行柱层析，除去杂质后旋转蒸发，得白色固体，即目标产物。
• 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.
• 586. Photochemical cyclisation of diels–alder adducts
  作者：R. C. Cookson、E. Crundwell、R. R. Hill、J. Hudec

  DOI：10.1039/jr9640003062

  日期：——
• Mehta, Goverdhan; Singh, Vishwakarma; Pandey, Paras N., Chemistry Letters, 1980, p. 59 - 62
  作者：Mehta, Goverdhan、Singh, Vishwakarma、Pandey, Paras N.、Chaudhury, B.、Duddeck, Helmut

  DOI：——

  日期：——
• Further studies in pentacycloundecan-8-one photochemistry
  作者：Ronald R. Sauers、Tyler A. Stevenson

  DOI：10.1021/jo00028a050

  日期：1992.1

  Three new syn-11-substituted pentacycloundecan-8-ones 1a-c (X = CN, CO2CH3, C6H5) have been synthesized and evaluated for photochemical reactivity in the context of the development of a force field methodology for evaluation of Norrish Type II reactions. None of these compounds underwent significant intramolecular hydrogen abstraction reactions or showed evidence for interactions between the excited alkanone and the proximate methylene hydrogens. The absence of isotope effect in the fluorescence of the deuteriated analogue of 1a provides strong evidence that there are no radiationless processes involving the proximate hydrogens that deactivate the singlet state of this ketone. A novel photostimulated interaction between alkanone singlet states and a ''remote'' cyano group was observed and rationalized in terms of dynamic processes during the excited state lifetime. Evidence is presented for competing long-range and contact interactions between singlet aryl rings and ground-state carbonyl groups. syn-11-tert-Butylpentacycloundecanone (2) was prepared and found to be photochemically unreactive as a consequence of a large increase in steric energy associated with formation of the transition structure.