11-ethyl-2-methyl-5,9-dioxa-7-pentadecanol | 93314-60-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 11-ethyl-2-methyl-5,9-dioxa-7-pentadecanol
• 英文别名: 1-(2-Ethylhexoxy)-3-(3-methylbutoxy)propan-2-ol
• CAS: 93314-60-4
• 化学式: C₁₆H₃₄O₃
• 分子量: 274.444
• InChiKey: RVMPLZXHBUADEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-ethyl-2-methyl-5,9-dioxa-7-pentadecanol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 11-ethyl-2-methyl-5,9-dioxa-7-pentadecanone
  参考文献：
  名称：

  Selective Synthesis of Aliphatic Ethylene Glycol Sulfonate Surfactants.

  摘要：

  The selective synthesis of a series of components in a commercial surfactant mixture was studied. The general structure of the surfactant was a glycerol-based double chain monosulfonate molecule, with a C-8-Guerbert alcohol, 2-ethylhexanol, at C-l, a pentyloxy group at C-3 and a 3-oxypropane-1-sulfonic acid or an ethoxylated 3-oxypropane-1-sulfonic acid side chain at the C-2 position. The main chain alcohol was obtained by a base catalyzed reaction of 2-ethylhexyl glycidyl ether with a pentyl alcohol. High C-3 selectivity was obtained. Two methods were used for the construction of the ethoxylated side chain at the C-2. A sequence consisting of O-allylation followed by ozonolysis and sodium borohydride work-up gave good yields of the desired ethoxylated homologs. A shorter, more efficient method involved the reaction with 1,2-ethylene sulfate. This method gave the ethoxylated homologs with high selectivity and in high yields. O-Propane sulfonation was accomplished by the reaction of the appropriate alkoxides with 1,3-propane sulfone. The pure sodium sulfonates were isolated in good overall yields by continuous extraction with hexane or diethyl ether.

  DOI：

  10.3891/acta.chem.scand.50-0170
• 作为产物：
  描述：

  辛基缩水甘油醚 、 异戊醇 在 sodium hydride 作用下， 反应 48.0h， 以79%的产率得到11-ethyl-2-methyl-5,9-dioxa-7-pentadecanol
  参考文献：
  名称：

  Selective Synthesis of Aliphatic Ethylene Glycol Sulfonate Surfactants.

  摘要：

  The selective synthesis of a series of components in a commercial surfactant mixture was studied. The general structure of the surfactant was a glycerol-based double chain monosulfonate molecule, with a C-8-Guerbert alcohol, 2-ethylhexanol, at C-l, a pentyloxy group at C-3 and a 3-oxypropane-1-sulfonic acid or an ethoxylated 3-oxypropane-1-sulfonic acid side chain at the C-2 position. The main chain alcohol was obtained by a base catalyzed reaction of 2-ethylhexyl glycidyl ether with a pentyl alcohol. High C-3 selectivity was obtained. Two methods were used for the construction of the ethoxylated side chain at the C-2. A sequence consisting of O-allylation followed by ozonolysis and sodium borohydride work-up gave good yields of the desired ethoxylated homologs. A shorter, more efficient method involved the reaction with 1,2-ethylene sulfate. This method gave the ethoxylated homologs with high selectivity and in high yields. O-Propane sulfonation was accomplished by the reaction of the appropriate alkoxides with 1,3-propane sulfone. The pure sodium sulfonates were isolated in good overall yields by continuous extraction with hexane or diethyl ether.

  DOI：

  10.3891/acta.chem.scand.50-0170

文献信息

• Selective Synthesis of Aliphatic Ethylene Glycol Sulfonate Surfactants.
  作者：Odd R. Gautun、Per H. J. Carlsen、Trygve Maldal、Olav Vikane、Eimund Gilje

  DOI：10.3891/acta.chem.scand.50-0170

  日期：——

  The selective synthesis of a series of components in a commercial surfactant mixture was studied. The general structure of the surfactant was a glycerol-based double chain monosulfonate molecule, with a C-8-Guerbert alcohol, 2-ethylhexanol, at C-l, a pentyloxy group at C-3 and a 3-oxypropane-1-sulfonic acid or an ethoxylated 3-oxypropane-1-sulfonic acid side chain at the C-2 position. The main chain alcohol was obtained by a base catalyzed reaction of 2-ethylhexyl glycidyl ether with a pentyl alcohol. High C-3 selectivity was obtained. Two methods were used for the construction of the ethoxylated side chain at the C-2. A sequence consisting of O-allylation followed by ozonolysis and sodium borohydride work-up gave good yields of the desired ethoxylated homologs. A shorter, more efficient method involved the reaction with 1,2-ethylene sulfate. This method gave the ethoxylated homologs with high selectivity and in high yields. O-Propane sulfonation was accomplished by the reaction of the appropriate alkoxides with 1,3-propane sulfone. The pure sodium sulfonates were isolated in good overall yields by continuous extraction with hexane or diethyl ether.