Ethanethioic acid, S-heptadecyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: Ethanethioic acid, S-heptadecyl ester
• 英文别名: S-heptadecyl ethanethioate
• 化学式: C₁₉H₃₈OS
• 分子量: 314.576
• InChiKey: FHHLKFQBXGYAKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  21
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethanethioic acid, S-heptadecyl ester 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 1-十七烷硫醇
  参考文献：
  名称：

  Intrinsic and Extrinsic Control of the pK_a of Thiol Guests inside Yoctoliter Containers

  摘要：

  Despite decades of research, there are still many open questions surrounding the mechanisms by which enzymes catalyze reactions. Understanding all the noncovalent forces involved has the potential to allow de novo catalysis design, and as a step toward this, understanding how to control the charge state of ionizable groups represents a powerful yet straightforward approach to probing complex systems. Here we utilize supramolecular capsules assembled via the hydrophobic effect to encapsulate guests and control their acidity. We find that the greatest influence on the acidity of bound guests is the location of the acidic group within the yoctoliter space. However, the nature of the electrostatic field generated by the (remote) charged solubilizing groups also plays a significant role in acidity, as does counterion complexation to the outer surfaces of the capsules. Taken together, these results suggest new ways by which to affect reactions in confined spaces.

  DOI：

  10.1021/jacs.0c00907
• 作为产物：
  描述：

  1-溴十七烷 、 potassium thioacetate 以 四氢呋喃 为溶剂， 生成 Ethanethioic acid, S-heptadecyl ester
  参考文献：
  名称：

  Intrinsic and Extrinsic Control of the pK_a of Thiol Guests inside Yoctoliter Containers

  摘要：

  Despite decades of research, there are still many open questions surrounding the mechanisms by which enzymes catalyze reactions. Understanding all the noncovalent forces involved has the potential to allow de novo catalysis design, and as a step toward this, understanding how to control the charge state of ionizable groups represents a powerful yet straightforward approach to probing complex systems. Here we utilize supramolecular capsules assembled via the hydrophobic effect to encapsulate guests and control their acidity. We find that the greatest influence on the acidity of bound guests is the location of the acidic group within the yoctoliter space. However, the nature of the electrostatic field generated by the (remote) charged solubilizing groups also plays a significant role in acidity, as does counterion complexation to the outer surfaces of the capsules. Taken together, these results suggest new ways by which to affect reactions in confined spaces.

  DOI：

  10.1021/jacs.0c00907