3,4-Bis-dodecyloxy-5-[12-(2-methyl-acryloyloxy)-dodecyloxy]-benzoic acid 4-{[1-p-tolyl-meth-(E)-ylidene]-amino}-phenyl ester | 477197-72-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 3,4-Bis-dodecyloxy-5-[12-(2-methyl-acryloyloxy)-dodecyloxy]-benzoic acid 4-{[1-p-tolyl-meth-(E)-ylidene]-amino}-phenyl ester
• 英文别名: [4-[(4-Methylphenyl)methylideneamino]phenyl] 3,4-didodecoxy-5-[12-(2-methylprop-2-enoyloxy)dodecoxy]benzoate；[4-[(4-methylphenyl)methylideneamino]phenyl] 3,4-didodecoxy-5-[12-(2-methylprop-2-enoyloxy)dodecoxy]benzoate
• CAS: 477197-72-1
• 化学式: C₆₁H₉₃NO₇
• 分子量: 952.412
• InChiKey: AILGJXSPDLNICN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.6
• 重原子数：
  69
• 可旋转键数：
  45
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-Bis-dodecyloxy-5-[12-(2-methyl-acryloyloxy)-dodecyloxy]-benzoic acid 4-{[1-p-tolyl-meth-(E)-ylidene]-amino}-phenyl ester 在 盐酸 、 silica gel 作用下， 以60%的产率得到4-{[3,4-di(dodecadecyloxy)-5-(12'-methylacrylatedodecadecyloxy)]benzoyloxy}aniline
  参考文献：
  名称：

  A facile route to multi-functionalization of methyl gallate: pivotal synthons for mesomorphic materials

  摘要：

  The preparation of mono-, di- and trisubstituted gallic derivatives is described using either 1-bromododecane or 12-bromo-1-dodecanol. After saponification of the methyl ester bearing the dodecanol groups, subsequent functionalization with methacryloyl chloride provides the hybrid methacrylate esters/anhydride species. Selective cleavage of the anhydride function gives rise to the corresponding acids, which have been further functionalized to the imine derivative 15 by condensation with 4-[imino-4-(toluyl)]phenol. This reaction is made possible using the acidic form of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC.HCI) and dimethylaminopyridine (DMAP). Selective hydrolysis of the imine function with a HCl-treated silica provides the targeted aniline in excellent yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01101-2
• 作为产物：
  描述：

  12-溴-1-十二烷醇 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氢氧化钾 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 3,4-Bis-dodecyloxy-5-[12-(2-methyl-acryloyloxy)-dodecyloxy]-benzoic acid 4-{[1-p-tolyl-meth-(E)-ylidene]-amino}-phenyl ester
  参考文献：
  名称：

  A facile route to multi-functionalization of methyl gallate: pivotal synthons for mesomorphic materials

  摘要：

  The preparation of mono-, di- and trisubstituted gallic derivatives is described using either 1-bromododecane or 12-bromo-1-dodecanol. After saponification of the methyl ester bearing the dodecanol groups, subsequent functionalization with methacryloyl chloride provides the hybrid methacrylate esters/anhydride species. Selective cleavage of the anhydride function gives rise to the corresponding acids, which have been further functionalized to the imine derivative 15 by condensation with 4-[imino-4-(toluyl)]phenol. This reaction is made possible using the acidic form of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC.HCI) and dimethylaminopyridine (DMAP). Selective hydrolysis of the imine function with a HCl-treated silica provides the targeted aniline in excellent yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01101-2