12-ethyl-8-(5-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecene | 174719-43-8

• 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: 12-ethyl-8-(5-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecene
• 英文别名: 3-[[3-(3-Methylbutoxy)-2-(2-prop-2-enoxyethoxy)propoxy]methyl]heptane
• CAS: 174719-43-8
• 化学式: C₂₁H₄₂O₄
• 分子量: 358.562
• InChiKey: VHHZQPPODGGOPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-ethyl-8-(5-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecene 在 sodium tetrahydroborate 、 sodium hydride 、 臭氧 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 15-ethyl-11-(5-methyl-2-oxa-1-hexyl)-4,7,10,13-tetraoxa-1-nonadecanesulfonic acid sodium salt
  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 在 sodium tetrahydroborate 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 92.0h， 生成 12-ethyl-8-(5-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecene
  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.