3-Hydroxy-4,5-bis-(12-hydroxy-dodecyloxy)-benzoic acid methyl ester | 477197-54-9

• 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: 3-Hydroxy-4,5-bis-(12-hydroxy-dodecyloxy)-benzoic acid methyl ester
• 英文别名: Methyl 3-hydroxy-4,5-bis(12-hydroxydodecoxy)benzoate；methyl 3-hydroxy-4,5-bis(12-hydroxydodecoxy)benzoate
• CAS: 477197-54-9
• 化学式: C₃₂H₅₆O₇
• 分子量: 552.792
• InChiKey: SNOYPAVHIDKYPV-UHFFFAOYSA-N

物化性质

• 沸点：
  683.9±50.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  39
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-4,5-bis-(12-hydroxy-dodecyloxy)-benzoic acid methyl ester 在 吡啶 、 氢氧化钾 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-Methylprop-2-enoyl 3-dodecoxy-4,5-bis[12-(2-methylprop-2-enoyloxy)dodecoxy]benzoate
  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 、 没食子酸甲酯 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到3,5-Dihydroxy-4-(12-hydroxy-dodecyloxy)-benzoic acid methyl 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

文献信息

• A facile route to multi-functionalization of methyl gallate: pivotal synthons for mesomorphic materials
  作者：Patrick Nguyen、Laurent Douce、Raymond Ziessel

  DOI：10.1016/s0040-4039(02)01101-2

  日期：2002.7

  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.