[26,27,28-Tribenzoyloxy-5,11,17,23-tetrakis(cyanomethyl)-25-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] benzoate | 161316-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [26,27,28-Tribenzoyloxy-5,11,17,23-tetrakis(cyanomethyl)-25-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] benzoate
• CAS: 161316-50-3
• 化学式: C₆₄H₄₄N₄O₈
• 分子量: 997.075
• InChiKey: SXYPJOOPJVVSFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  76
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  200
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  对甲基苯甲醛 、 [26,27,28-Tribenzoyloxy-5,11,17,23-tetrakis(cyanomethyl)-25-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] benzoate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到5,11,17,23-Tetrakis<1-cyano-2-(4'-methylphenyl)ethenyl>-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
• 作为产物：
  描述：

  p-cyanomethylcalix[4]arene 在 N-甲基咪唑 、 三氯化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [26,27,28-Tribenzoyloxy-5,11,17,23-tetrakis(cyanomethyl)-25-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] benzoate
  参考文献：
  名称：

  Aroylation and Acylation ofp-Cyanomethylcalix[4]arenes

  摘要：

  携带H、叔丁基和氰甲基集团的p-位Calix[4]arenes在1-甲基咪唑或氢化钠存在下经过芳酰化或酰化反应转化为四酯。在氯化铝的存在下对p-氰甲基Calix[4]arene进行芳酰化或酰化反应，可以得到1,3-二酯，进一步进行芳酰化或酰化反应则可得到多种功能混合的四酯。

  DOI：

  10.1055/s-1994-25581

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：——