5,11-dibutyl-1,2,3,4,6,7,9,10,12,13,14,15-dodecahydroacridino[4,3-b]benzo[j][1,10]phenanthroline di-N-oxide | 105309-56-6

• 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: 5,11-dibutyl-1,2,3,4,6,7,9,10,12,13,14,15-dodecahydroacridino[4,3-b]benzo[j][1,10]phenanthroline di-N-oxide
• 英文别名: 12,22-dibutyl-5,29-dioxido-2-aza-5,29-diazoniaheptacyclo[16.12.0.03,16.04,13.06,11.021,30.023,28]triaconta-1,3(16),4,6(11),12,17,21,23(28),29-nonaene
• CAS: 105309-56-6
• 化学式: C₃₅H₄₃N₃O₂
• 分子量: 537.745
• InChiKey: YPDYQISULSRZGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

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 di-N-oxide 在 盐酸 、 硫酸 、 sodium acetate 、 戴斯-马丁氧化剂 、 乙酰氯 作用下， 以 水 、 乙腈 为溶剂， 反应 2.59h， 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-4-[1-phenyl-meth-(E)-ylidene]-1,2,3,4,5,6,7,8-octahydro-acridine 在 二甲基硫 、 ammonium acetate 、 氧气 、 sodium hydride 、 对甲苯磺酸 、 臭氧 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 58.0h， 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 di-N-oxide
  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

文献信息

• BELL T. W.; FIRESTONE A., J. AMER. CHEM. SOC., 108,(1986) N 25, 8109-8111
  作者：BELL T. W.、 FIRESTONE A.

  DOI：——

  日期：——