5,11,17,23-Tetrakis<1-cyano-2-phenylethenyl>-25,26,27,28-tetrahydroxycalix<4>arene | 165317-15-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5,11,17,23-Tetrakis<1-cyano-2-phenylethenyl>-25,26,27,28-tetrahydroxycalix<4>arene
• 英文别名: (Z)-3-phenyl-2-[11,17,23-tris[(Z)-1-cyano-2-phenylethenyl]-25,26,27,28-tetrahydroxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]prop-2-enenitrile
• CAS: 165317-15-7
• 化学式: C₆₄H₄₄N₄O₄
• 分子量: 933.078
• InChiKey: NJYNBWHAEAWZOP-NMEMZEFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  72
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  176
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 5,11,17,23-Tetrakis<1-cyano-2-phenylethenyl>-25,26,27,28-tetrahydroxycalix<4>arene 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以88%的产率得到5,11,17,23-Tetrakis(1-cyano-2-phenylethenyl)-25,26,27,28-tetrakis(benzyloxy)calix<4>arene
  参考文献：
  名称：

  Calixarenes. 40. Arylmethylenation of p-(Cyanomethyl)calix[4]arene

  摘要：

  Treatment of tetra-O-substituted p-(cyanomethyl)calix[4]arenes 3 and 6 with aromatic aldehydes yields aldol product resulting from condensation at the carbons a to the cyano groups. The products 4 from the tetra-O-benzyl compound 3 retain the benzyl groups and are formed in the 1,3-alternate conformation. The products 7 from the tetra-O-benzoyl compounds 6, however, involve loss of the benzoyl groups and are formed in the cone conformation. The same phenolic compounds 7 can be obtained from the O-benzyl compounds 4 by Lewis acid-induced removal of the benzyl groups. Reintroduction of the benzyl groups by treating 7 with benzyl bromide produces the tetra-O-benzylated product in the cone conformation (12) when NaH is used as the base or in the 1,3-alternate conformation (4) when K2CO3 is used as the base. Benzoylation of 7 produces the tetra-O-benzoyl compound in the 1,3-alternate conformation (10) when 1-methylimidazole is used as the base or the 1,3-di-O-benzoyl compound in a flattened cone conformation (11) when AlCl3 is used as the catalyst. H-1 NMR and C-13 NMR data provide support for the conformational assignments, and UV data suggest a twisting of the conjugated system in the 2'-substituted compounds 4b/7b (2'-methoxyphenyl), 4e/7e (2'-methylphenyl), and 4g/7g (2'-chlorophenyl).

  DOI：

  10.1021/jo00099a038
• 作为产物：
  描述：

  5,11,17,23-Tetrakis(1-cyano-2-phenylethenyl)-25,26,27,28-tetrakis(benzyloxy)calix<4>arene 在 三氯化铝 作用下， 以 甲苯 为溶剂， 以95%的产率得到5,11,17,23-Tetrakis<1-cyano-2-phenylethenyl>-25,26,27,28-tetrahydroxycalix<4>arene
  参考文献：
  名称：

  Calixarenes. 40. Arylmethylenation of p-(Cyanomethyl)calix[4]arene

  摘要：

  Treatment of tetra-O-substituted p-(cyanomethyl)calix[4]arenes 3 and 6 with aromatic aldehydes yields aldol product resulting from condensation at the carbons a to the cyano groups. The products 4 from the tetra-O-benzyl compound 3 retain the benzyl groups and are formed in the 1,3-alternate conformation. The products 7 from the tetra-O-benzoyl compounds 6, however, involve loss of the benzoyl groups and are formed in the cone conformation. The same phenolic compounds 7 can be obtained from the O-benzyl compounds 4 by Lewis acid-induced removal of the benzyl groups. Reintroduction of the benzyl groups by treating 7 with benzyl bromide produces the tetra-O-benzylated product in the cone conformation (12) when NaH is used as the base or in the 1,3-alternate conformation (4) when K2CO3 is used as the base. Benzoylation of 7 produces the tetra-O-benzoyl compound in the 1,3-alternate conformation (10) when 1-methylimidazole is used as the base or the 1,3-di-O-benzoyl compound in a flattened cone conformation (11) when AlCl3 is used as the catalyst. H-1 NMR and C-13 NMR data provide support for the conformational assignments, and UV data suggest a twisting of the conjugated system in the 2'-substituted compounds 4b/7b (2'-methoxyphenyl), 4e/7e (2'-methylphenyl), and 4g/7g (2'-chlorophenyl).

  DOI：

  10.1021/jo00099a038

文献信息

• Sharma Shiv Kumar, Gutsche C. David, J. Org. Chem, 59 (1994) N 20, S 6030-6037
  作者：Sharma Shiv Kumar, Gutsche C. David

  DOI：——

  日期：——
• Calixarenes. 40. Arylmethylenation of p-(Cyanomethyl)calix[4]arene
  作者：Shiv Kumar Sharma、C. David Gutsche

  DOI：10.1021/jo00099a038

  日期：1994.10

  Treatment of tetra-O-substituted p-(cyanomethyl)calix[4]arenes 3 and 6 with aromatic aldehydes yields aldol product resulting from condensation at the carbons a to the cyano groups. The products 4 from the tetra-O-benzyl compound 3 retain the benzyl groups and are formed in the 1,3-alternate conformation. The products 7 from the tetra-O-benzoyl compounds 6, however, involve loss of the benzoyl groups and are formed in the cone conformation. The same phenolic compounds 7 can be obtained from the O-benzyl compounds 4 by Lewis acid-induced removal of the benzyl groups. Reintroduction of the benzyl groups by treating 7 with benzyl bromide produces the tetra-O-benzylated product in the cone conformation (12) when NaH is used as the base or in the 1,3-alternate conformation (4) when K2CO3 is used as the base. Benzoylation of 7 produces the tetra-O-benzoyl compound in the 1,3-alternate conformation (10) when 1-methylimidazole is used as the base or the 1,3-di-O-benzoyl compound in a flattened cone conformation (11) when AlCl3 is used as the catalyst. H-1 NMR and C-13 NMR data provide support for the conformational assignments, and UV data suggest a twisting of the conjugated system in the 2'-substituted compounds 4b/7b (2'-methoxyphenyl), 4e/7e (2'-methylphenyl), and 4g/7g (2'-chlorophenyl).