6-oxa-1-octyl 4-methylbenzenesulfonate | 131178-96-6

• 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: 6-oxa-1-octyl 4-methylbenzenesulfonate
• 英文别名: 6-oxaoctyl p-toluenesulfonate；5-Ethoxypentyl 4-methylbenzenesulfonate
• CAS: 131178-96-6
• 化学式: C₁₄H₂₂O₄S
• 分子量: 286.392
• InChiKey: JMTBOVQUNZRIAH-UHFFFAOYSA-N

物化性质

• 沸点：
  128-134 °C(Press: 0.08 Torr)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-oxa-1-octyl 4-methylbenzenesulfonate 在 sodium dichromate 、 硫酸 、 水 、 sodium hydride 、 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 反应 34.0h， 生成 6,12-dioxatetradecanoic acid
  参考文献：
  名称：

  Nucleophile-dependent substitution reactions of 5-halovaleric acid esters: synthesis of 6,12-dioxamyristic acid

  摘要：

  The reaction of 5-ethoxypentan-1-ol with a variety of 5-halovalerate alkyl esters afforded ester exchange products rather than the expected products of Williamson ether synthesis. The virtually unknown reaction of an alkoxide with a 5-halovalerate ester contrasts strongly with literature reports of reactions involving other nucleophiles in which the halogen substitution products are nearly always isolated. An explanation is offered for this behavior in terms of a chelation-induced conformation of the substrate. Although the direct synthetic approach failed, the hitherto unknown title compound could still be prepared, albeit in six steps in 6% overall yield. The approach used is discussed along with the interesting chemistry of this system.

  DOI：

  10.1021/jo00002a046
• 作为产物：
  描述：

  1,5-戊二醇 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 53.0h， 生成 6-oxa-1-octyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Nucleophile-dependent substitution reactions of 5-halovaleric acid esters: synthesis of 6,12-dioxamyristic acid

  摘要：

  The reaction of 5-ethoxypentan-1-ol with a variety of 5-halovalerate alkyl esters afforded ester exchange products rather than the expected products of Williamson ether synthesis. The virtually unknown reaction of an alkoxide with a 5-halovalerate ester contrasts strongly with literature reports of reactions involving other nucleophiles in which the halogen substitution products are nearly always isolated. An explanation is offered for this behavior in terms of a chelation-induced conformation of the substrate. Although the direct synthetic approach failed, the hitherto unknown title compound could still be prepared, albeit in six steps in 6% overall yield. The approach used is discussed along with the interesting chemistry of this system.

  DOI：

  10.1021/jo00002a046

文献信息

• Amphiphilic Organocatalyst for Schotten-Baumann-Type Tosylation of Alcohols under Organic Solvent Free Condition
  作者：Keisuke Asano、Seijiro Matsubara

  DOI：10.1021/ol900125y

  日期：2009.4.16

  A Tosylation of primary alcohol with tosyl chloride was performed effectively with an N-hexadecylimidazole catalyst in water containing K2CO3. aggregation of the catalyst carrying a hydrophobic methylene chain worked as a substitute for organic solvent.

  N-十六烷基咪唑催化剂可在含K 2 CO 3的水中有效地进行伯醇与甲苯磺酰氯的甲苯磺酸酯化反应。带有疏水性亚甲基链的催化剂的聚集体用作有机溶剂的替代物。
• KATOH, AKIRA;LU, TIANBAO;DEVADAS, B.;ADAMS, STEVEN P.;GORDON, JEFFREY I.;+, J. ORG. CHEM., 56,(1991) N, C. 731-735
  作者：KATOH, AKIRA、LU, TIANBAO、DEVADAS, B.、ADAMS, STEVEN P.、GORDON, JEFFREY I.、+

  DOI：——

  日期：——
• Novel fatty acid analog enzyme substrates
  申请人：WASHINGTON UNIVERSITY

  公开号：EP0441765B1

  公开（公告）日：1994-05-11
• Nucleophile-dependent substitution reactions of 5-halovaleric acid esters: synthesis of 6,12-dioxamyristic acid
  作者：Akira Katoh、Tianbao Lu、B. Devadas、Steven P. Adams、Jeffrey I. Gordon、George W. Gokel

  DOI：10.1021/jo00002a046

  日期：1991.1

  The reaction of 5-ethoxypentan-1-ol with a variety of 5-halovalerate alkyl esters afforded ester exchange products rather than the expected products of Williamson ether synthesis. The virtually unknown reaction of an alkoxide with a 5-halovalerate ester contrasts strongly with literature reports of reactions involving other nucleophiles in which the halogen substitution products are nearly always isolated. An explanation is offered for this behavior in terms of a chelation-induced conformation of the substrate. Although the direct synthetic approach failed, the hitherto unknown title compound could still be prepared, albeit in six steps in 6% overall yield. The approach used is discussed along with the interesting chemistry of this system.