(5E)-5-benzylidene-9-butyl-2,3,4,6,7,8-hexahydro-1H-acridin-4-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (5E)-5-benzylidene-9-butyl-2,3,4,6,7,8-hexahydro-1H-acridin-4-ol
• 英文别名: (5E)-5-benzylidene-9-butyl-2,3,4,6,7,8-hexahydro-1H-acridin-4-ol;hydrobromide
• 化学式: BrH*C₂₄H₂₉NO
• 分子量: 428.412
• InChiKey: ITQZXYZRLNINFE-HYNBPGMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  33.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-n-butyl-1,2,3,4,5,6,7,8-octahydroacridine N-oxide 在 氢溴酸 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 生成 (5E)-5-benzylidene-9-butyl-2,3,4,6,7,8-hexahydro-1H-acridin-4-ol
  参考文献：
  名称：

  Molecular Architecture. 2.¹ Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts

  摘要：

  Methods are described for the synthesis of a series of functionalized derivatives of 9-butyl-1,2,3,4,5,6,7,8-octahydroacridine (9), a building block for several types of highly preorganized host compounds. A key intermediate is 5-benzylidene-9-butyl-2,3,5,6,7,8-hexahydroacridin-4(1H)-one (23), which can also be used in the syntheses of torands and hydrogen-bonding hexagonal lattice receptors. A tridentate cleft (20), consisting of 2,2';6',2 "-terpyridine imbedded in a heptacyclic framework, and a corresponding pentadentate diketone (6) were synthesized from 9 in five and seven steps, respectively. The picrate extraction method was used to estimate the solution stabilities of alkali metal complexes of heptacyclic terpyridyls 6 and 20, which was also compared with a flexible terpyridyl (37). Alkali metal complexes of both heptacyclic terpyridyls showed relatively high K-s values, but low size selectivity. Pentadentate host 6 binds Na+ and K+ more strongly than do most hexadentate crown ethers; flexible tridentate analogue 37 failed to extract alkali metal picrates into chloroform. The complexation abilities of 6 and 20 are attributed to enforced orientation of functional group dipoles toward the center of the molecular cleft. Sodium and potassium picrate complexes of pentadentate cleft 6 were synthesized (1:1 stoichiometry), and a 2:1 complex of calcium triflate (6(2) . Ca(CF3SO3)(2)) was also prepared.

  DOI：

  10.1021/jo9720041