6,6-Ethylendioxypentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decan | 57293-86-4

• 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: 6,6-Ethylendioxypentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decan
• 英文别名: pentacyclo-[5.3.0.0(2,5).0(3,9).0(4,8)]decan-10-one ethyleneketal；ethylene ketal of pentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)]decan-6-one；spiro[1,3-dioxolane-2,6'-pentacyclo[5.3.0.02,5.03,9.04,8]decane]
• CAS: 57293-86-4
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: XJAAQTVRIUIUDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6,6-Ethylendioxypentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decan 以90%的产率得到
  参考文献：
  名称：

  HIRAO KEN-ICHI; IWAKUMA TAKEO; TANIGUCHI MIKIO; YONEMITSU OSAMU; DATE TAD+, J. CHEM. SOC. PERKIN TRANS., 1980, PART 1, NO 1, 163-169

  摘要：

  DOI：
• 作为产物：
  描述：

  pentacyclo(5.3.0.0^{2,5_.03,9_.04,8})deca-6,10-dione-6-ethylene ketal 在 四氯化碳 、 lithium aluminium tetrahydride 、 lithium 、 三苯基膦 、 叔丁醇 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 6,6-Ethylendioxypentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decan
  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

• Convenient preparative synthesis of pentacyclo[5.3.0.02,5.03,9.04,8]decane (C 2-Bishomocubane)
  作者：A. S. Sklyarova、V. N. Rodionov、A. A. Fokin

  DOI：10.1134/s1070428009110098

  日期：2009.11

  By reaction of pentacyclo[5.3.0.02,5.03,9.04,8]decane-6,10-dione 6-ethyleneketal with lithium aluminum hydride the corresponding hydroxyketal was obtained whose hydroxy group was replaced by chlorine at boiling in CCl4 in the presence of a 15% molar excess of triphenylphosphine. 6-Ethyleneketal of pentacyclo-[5.3.0.02,5.03,9.04,8]decan-6-one obtained by dechlorination of the chloroketal in a system

  通过五环[5.3.0.0 2,5 .0 3,9 .0 4,8 ]癸烷-6,10-二酮6-乙烯缩酮与氢化铝锂反应，得到相应的羟基缩酮，其羟基在沸腾时被氯取代在15％摩尔过量的三苯基膦存在下于CCl 4中溶解。通过在THF中的叔丁基锂中将氯缩酮脱氯制得的五环的[6-乙烯缩酮-[5.3.0.0 2,5 .0 3,9 .0 4,8 ] decan-6-通过以下方式水解为酮在THF存在下，在10％硫酸中加热。所获得的酮沿着沃尔夫-基什纳反应还原为五环[5.3.0.0 2,5 .0 3,9.0 4,8 ]癸烷。
• 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
• 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.
• HIRAO KEN-ICHI; IWAKUMA TAKEO; TANIGUCHI MIKIO; YONEMITSU OSAMU; DATE TAD+, J. CHEM. SOC. PERKIN TRANS., 1980, PART 1, NO 1, 163-169
  作者：HIRAO KEN-ICHI、 IWAKUMA TAKEO、 TANIGUCHI MIKIO、 YONEMITSU OSAMU、 DATE TAD+

  DOI：——

  日期：——