4-azatetracyclo[7.3.1.1^7,11.0^2,7]tetradecan-5-one | 1142949-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-azatetracyclo[7.3.1.1^7,11.0^2,7]tetradecan-5-one
• 英文别名: 4-Azatetracyclo[7.3.1.17,11.02,7]tetradecan-5-one；4-azatetracyclo[7.3.1.17,11.01,6]tetradecan-3-one
• CAS: 1142949-93-6
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: XLTIJTZKRZXVJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-azatetracyclo[7.3.1.1^7,11.0^2,7]tetradecan-5-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 4-azatetracyclo[7.3.1.1(7,11).0(2,7)]tetradecane
  参考文献：
  名称：

  Design and synthesis of 1,2-annulated adamantane piperidines with anti-influenza virus activity

  摘要：

  1-2 Annulated adamantane piperidines 4, 6, 16, 17, 19, 23 and 25 were synthesized and evaluated for anti-influenza A virus activity. The stereoelectronic requirements for optimal antiviral potency were investigated. Piperidine 23 proved to be the most active of the compounds tested against influenza A virus, being 3.5-fold more active than amantadine, equipotent to rimantadine and 15-fold more potent than ribavirin. It is noteworthy that piperidine 23 displayed one of the highest selectivity indexes (SI>732) among aminoadamantanes or other cage structure amines tested till now. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.009
• 作为产物：
  描述：

  ethyl (2-cyanotricyclo[3.3.1.1^3,7]dec-1-yl)acetate 在 氢气 、 镍 作用下， 以 乙醇 为溶剂， 140.0 ℃ 、379.22 kPa 条件下， 反应 7.0h， 以21%的产率得到4-azatetracyclo[7.3.1.1^7,11.0^2,7]tetradecan-5-one
  参考文献：
  名称：

  Design and synthesis of 1,2-annulated adamantane piperidines with anti-influenza virus activity

  摘要：

  1-2 Annulated adamantane piperidines 4, 6, 16, 17, 19, 23 and 25 were synthesized and evaluated for anti-influenza A virus activity. The stereoelectronic requirements for optimal antiviral potency were investigated. Piperidine 23 proved to be the most active of the compounds tested against influenza A virus, being 3.5-fold more active than amantadine, equipotent to rimantadine and 15-fold more potent than ribavirin. It is noteworthy that piperidine 23 displayed one of the highest selectivity indexes (SI>732) among aminoadamantanes or other cage structure amines tested till now. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.009

文献信息

• An intriguing and facile one-pot catalytic synthesis of N-alkylated lactams
  作者：Grigoris Zoidis、Lieve Naesens、Erik De Clercq

  DOI：10.1007/s00706-013-0924-8

  日期：2013.4

  Catalyzed by Raney nickel, hydrogenation of 1,2-adamantane oxime esters or cyano esters afforded the unexpected N-alkylated lactams in good to moderate yields, probably proceeding through the so-called hydrogen autotransfer process. This reaction provided an efficient one-pot method for synthesis of N-alkylated lactams which had significant anti-influenza A activity.
• Design and synthesis of 1,2-annulated adamantane piperidines with anti-influenza virus activity
  作者：Grigoris Zoidis、Nicolas Kolocouris、Lieve Naesens、Erik De Clercq

  DOI：10.1016/j.bmc.2009.01.009

  日期：2009.2

  1-2 Annulated adamantane piperidines 4, 6, 16, 17, 19, 23 and 25 were synthesized and evaluated for anti-influenza A virus activity. The stereoelectronic requirements for optimal antiviral potency were investigated. Piperidine 23 proved to be the most active of the compounds tested against influenza A virus, being 3.5-fold more active than amantadine, equipotent to rimantadine and 15-fold more potent than ribavirin. It is noteworthy that piperidine 23 displayed one of the highest selectivity indexes (SI>732) among aminoadamantanes or other cage structure amines tested till now. (c) 2009 Elsevier Ltd. All rights reserved.