5-[2-[2-(2-Prop-2-enoxyethoxy)ethoxy]ethoxymethyl]undecane | 1026252-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[2-[2-(2-Prop-2-enoxyethoxy)ethoxy]ethoxymethyl]undecane
• CAS: 1026252-35-6
• 化学式: C₂₁H₄₂O₄
• 分子量: 358.562
• InChiKey: NVRKOGJGLJDWPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  21
• 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：

  5-[2-[2-(2-Prop-2-enoxyethoxy)ethoxy]ethoxymethyl]undecane 在 sodium hydrogensulfite 、 sodium sulfite 作用下， 以 水 为溶剂， 反应 3.0h， 生成 15-Butyl-4,7,10,13-tetraoxaheneicosane-1-sulfonic acid sodium salt
  参考文献：
  名称：

  Surfactant-Mediated Phase Transfer as an Alternative to Propanesultone Alkylation. Formation of a New Class of Zwitterionic Surfactants

  摘要：

  A synthesis of propanesulfonate surfactants 5 is presented which avoids carcinogenic propanesultone 2 as an alkylating agent. A small amount of the final desired surfactant or an easily destroyed sulfate surfactant is added to a starting alcohol 3 as a phase transfer agent, the alcohol is converted to its corresponding allyl ether 4 with 50% NaOH and allyl chloride, and the allyl ether is converted to propane sulfonate 5 by air-catalyzed addition of bisulfite. Diallyl ether produced as a solvolysis byproduct is cyclized to furan sulfonate 9. Cyclization of diallylamine with bisulfite produces pyrrolidinium sulfonate 13 and diallylmethylalkylammonium salts 14 yield a new class of zwitterionic surfactants 11 which are substantially more soluble in both water and hydrocarbons than the corresponding ammonium propanesulfonates, 12. The stereochemistry of the cyclic products is consistent with a radical chain mechanism for the addition of bisulfite.

  DOI：

  10.1021/jo00122a028
• 作为产物：
  描述：

  2-(2'-(2''-Chloroethoxy)ethoxy)ethyl-2-tetrahydro-2H-pyran 在 sodium hydroxide 、 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 反应 22.0h， 生成 5-[2-[2-(2-Prop-2-enoxyethoxy)ethoxy]ethoxymethyl]undecane
  参考文献：
  名称：

  Surfactant-Mediated Phase Transfer as an Alternative to Propanesultone Alkylation. Formation of a New Class of Zwitterionic Surfactants

  摘要：

  A synthesis of propanesulfonate surfactants 5 is presented which avoids carcinogenic propanesultone 2 as an alkylating agent. A small amount of the final desired surfactant or an easily destroyed sulfate surfactant is added to a starting alcohol 3 as a phase transfer agent, the alcohol is converted to its corresponding allyl ether 4 with 50% NaOH and allyl chloride, and the allyl ether is converted to propane sulfonate 5 by air-catalyzed addition of bisulfite. Diallyl ether produced as a solvolysis byproduct is cyclized to furan sulfonate 9. Cyclization of diallylamine with bisulfite produces pyrrolidinium sulfonate 13 and diallylmethylalkylammonium salts 14 yield a new class of zwitterionic surfactants 11 which are substantially more soluble in both water and hydrocarbons than the corresponding ammonium propanesulfonates, 12. The stereochemistry of the cyclic products is consistent with a radical chain mechanism for the addition of bisulfite.

  DOI：

  10.1021/jo00122a028

文献信息

• Surfactant-Mediated Phase Transfer as an Alternative to Propanesultone Alkylation. Formation of a New Class of Zwitterionic Surfactants
  作者：Kirk D. Schmitt

  DOI：10.1021/jo00122a028

  日期：1995.9

  A synthesis of propanesulfonate surfactants 5 is presented which avoids carcinogenic propanesultone 2 as an alkylating agent. A small amount of the final desired surfactant or an easily destroyed sulfate surfactant is added to a starting alcohol 3 as a phase transfer agent, the alcohol is converted to its corresponding allyl ether 4 with 50% NaOH and allyl chloride, and the allyl ether is converted to propane sulfonate 5 by air-catalyzed addition of bisulfite. Diallyl ether produced as a solvolysis byproduct is cyclized to furan sulfonate 9. Cyclization of diallylamine with bisulfite produces pyrrolidinium sulfonate 13 and diallylmethylalkylammonium salts 14 yield a new class of zwitterionic surfactants 11 which are substantially more soluble in both water and hydrocarbons than the corresponding ammonium propanesulfonates, 12. The stereochemistry of the cyclic products is consistent with a radical chain mechanism for the addition of bisulfite.