(5E)-5-benzylidene-9-butyl-3-methylidene-2,6,7,8-tetrahydro-1H-acridin-4-one | 135075-51-3

• 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-3-methylidene-2,6,7,8-tetrahydro-1H-acridin-4-one
• CAS: 135075-51-3
• 化学式: C₂₅H₂₇NO
• 分子量: 357.495
• InChiKey: ROKHFBUFVHTNNY-KNTRCKAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5E)-5-benzylidene-9-butyl-3-methylidene-2,6,7,8-tetrahydro-1H-acridin-4-one 在 二甲基硫 、 ammonium acetate 、 臭氧 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Expanded heterohelicenes: molecular coils that form chiral complexes

  摘要：

  DOI：

  10.1021/ja00016a062
• 作为产物：
  描述：

  {9-Butyl-4-oxo-5-[1-phenyl-meth-(E)-ylidene]-1,2,3,4,5,6,7,8-octahydro-acridin-3-ylmethyl}-trimethyl-ammonium; iodide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以3.78 g的产率得到(5E)-5-benzylidene-9-butyl-3-methylidene-2,6,7,8-tetrahydro-1H-acridin-4-one
  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

• Expanded heterohelicenes: molecular coils that form chiral complexes
  作者：Thomas W. Bell、Helene Jousselin

  DOI：10.1021/ja00016a062

  日期：1991.7
• Molecular Architecture. 2.¹ Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts
  作者：Thomas W. Bell、Peter J. Cragg、Albert Firestone、Albert D.-I. Kwok、Jia Liu、Richard Ludwig、Andrej Sodoma

  DOI：10.1021/jo9720041

  日期：1998.4.1

  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.