Spiro(1,3-dioxolane-2,10'-tricyclo[5.2.1.0~2,6~]deca[4,8]diene)-3'-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Spiro(1,3-dioxolane-2,10'-tricyclo[5.2.1.0~2,6~]deca[4,8]diene)-3'-one
• 英文别名: spiro[1,3-dioxolane-2,10'-tricyclo[5.2.1.02,6]deca-4,8-diene]-3'-one
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: HQKBGTDYJMQTDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Spiro(1,3-dioxolane-2,10'-tricyclo[5.2.1.0~2,6~]deca[4,8]diene)-3'-one 以99%的产率得到pentacyclo(5.3.0.0^{2,5_.03,9_.04,8})deca-6,10-dione-6-ethylene ketal
  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

• Tandem Cope–cheletropic reaction: a new molecular rearrangement
  作者：Dipakranjan Mal、Nirmal K. Hazra

  DOI：10.1039/cc9960001181

  日期：——

  The pentacyclic naphthoquinones 8 undergo unprecedented thermal rearrangement to cyclopent[a]anthraquinones 7 or 9 via a tandem Cope-cheletropic reaction path.
• 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.