5,11-dibutyl-1,2,3,4,6,7,9,10,12,13,14,15-dodecahydroacridino[4,3-b]benzo[j][1,10]phenanthroline-1,5-diol diacetate | 203641-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 5,11-dibutyl-1,2,3,4,6,7,9,10,12,13,14,15-dodecahydroacridino[4,3-b]benzo[j][1,10]phenanthroline-1,5-diol diacetate
• CAS: 203641-00-3
• 化学式: C₃₉H₄₇N₃O₄
• 分子量: 621.82
• InChiKey: YHGGBNPLGHLSPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  91.27
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5,11-dibutyl-1,2,3,4,6,7,9,10,12,13,14,15-dodecahydroacridino[4,3-b]benzo[j][1,10]phenanthroline-1,5-diol diacetate 在 盐酸 、 硫酸 、 戴斯-马丁氧化剂 作用下， 以 水 、 乙腈 为溶剂， 反应 1.59h， 生成 5,11-dibutyl-2,3,4,6,7,9,10,12,13,14-decahydroacridino[4,3-b]benzo[j][1,10]phenanthroline-1,15-dione
  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
• 作为产物：
  描述：

  9-Butyl-3-[1-hydroxy-meth-(E)-ylidene]-2,3,5,6,7,8-hexahydro-1H-acridin-4-one 在 ammonium acetate 、 sodium acetate 、 sodium hydride 、 对甲苯磺酸 、 乙酰氯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 5,11-dibutyl-1,2,3,4,6,7,9,10,12,13,14,15-dodecahydroacridino[4,3-b]benzo[j][1,10]phenanthroline-1,5-diol diacetate
  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