N-(pentacyclo[6.3.0.02,6.03,10.05,9]undecan-4-ylidene)hydroxylamine | 1353687-38-3

• 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: N-(pentacyclo[6.3.0.02,6.03,10.05,9]undecan-4-ylidene)hydroxylamine
• 英文别名: N-(pentacyclo[6.3.0.0^2,6.0^3,10.0^5,9]undecan-4-ylidene)hydroxylamine；pentacyclo[6.3.0.0(2,6).0(3,10).0(5,9)]undecan-4-one oxime
• CAS: 1353687-38-3
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: DWFXTMHTECXDJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(pentacyclo[6.3.0.02,6.03,10.05,9]undecan-4-ylidene)hydroxylamine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以19%的产率得到pentacyclo[6.3.0.0^2,6.0^3,10.0^5,9]undecyl-4-amine
  参考文献：
  名称：

  Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists

  摘要：

  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.

  DOI：

  10.1007/s00044-012-0029-7
• 作为产物：
  描述：

  anti-11-hydroxypentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8-one 在 吡啶 、 chromium(VI) oxide 、 硫酸 、 盐酸羟胺 、 肼 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 N-(pentacyclo[6.3.0.02,6.03,10.05,9]undecan-4-ylidene)hydroxylamine
  参考文献：
  名称：

  Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists

  摘要：

  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.

  DOI：

  10.1007/s00044-012-0029-7

文献信息

• Selective reductive dimerization of homocubane series oximes
  作者：V. N. Rodionov、A. S. Sklyarova、T. V. Shamota、P. R. Schreiner、A. A. Fokin

  DOI：10.1134/s1070428011110078

  日期：2011.11

  ketal of the pentacyclo[5.3.0.02,5.03,9.04,8] decan-6-one obtained by the debromination of ethylene ketals of 4,7- and 5,8-dibromopentacyclo[5.3.0.02,5.03,9.04,8] decan-6-one was hydrolyzed to ketone whose oxime was selectively reduced on a platinum catalyst into the di-6-pentacyclo[5.3.0.02,5.03,9.04,8]decylamine. The reaction of reductive dimerization was also characteristic of pentacyclo[4.3.0.02,5

  由1,9-二溴戊酰基氯[5.4.0.0 2,6 .0 3,10 .0 5,9 ] -undeca-8,11-二酮反应，然后水解和环化而制得的二乙烯缩酮和单乙烯缩酮的混合物通过Faworsky方法进行的收缩转化为7-溴五环[5.3.0.0 2,5 .0 3,9 .0 4,8 ] decan-6-one-4-和5-溴五环[5.3.0.0]的乙烯缩酮的混合物2,5 .0 3,9 .0 4,8 ]癸烷-6-一-8-羧酸，其中羧基按照Hunsdiecker-Borodine-Cristol的方法被溴取代。五环的6-乙烯缩酮[5.3.0.0 2,5 .0 3,9 .0 4,8通过将4,7-和5,8-二溴五环[5.3.0.0 2,5 .0 3,9 .0 4,8 ] decan-6-的乙烯酮缩酮脱溴制得的] decan-6-被水解为酮，其肟在铂催化剂上选择性地还原成二-6-五环[5.3.0.0 2,5 .0