12-(acetylthio)dodecyl 4-acetoxybenzoate | 1591912-19-4

• 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: 12-(acetylthio)dodecyl 4-acetoxybenzoate
• CAS: 1591912-19-4
• 化学式: C₂₃H₃₄O₅S
• 分子量: 422.586
• InChiKey: XHHQFJROLOQLNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  29.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  12-(acetylthio)dodecyl 4-acetoxybenzoate 在 sodium thiomethoxide 作用下， 以 甲醇 为溶剂， 以36%的产率得到12-mercaptododecyl 4-hydroxybenzoate
  参考文献：
  名称：

  Efficient Preparation of Novel Phenolic Surfactants for Self-Assembled Monolayers

  摘要：

  Novel molecules have been synthesized that combine the phenolic nature of tannins and self-assembling properties of surfactants. These single-chain (C-12) surfactants with potential biocompatibility have been synthesized with an omega-thiol or disulfide functionality, both commonly used anchors in self-assembly onto gold surfaces, using a modular route. Protecting groups for the phenol and thiol moieties played a key role for overcoming the challenges often associated with the purification of surfactants. The tasks of unmasking the thiol moiety and simultaneously deprotecting the acetyl protecting groups of the phenols were accomplished using sodium thiomethoxide. This modular route can be extended to synthesize other surfactants with the potential ability to form robust layers with biocompatible properties.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.844259
• 作为产物：
  描述：

  对羟基苯甲酸 在 氯化亚砜 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 102.0h， 生成 12-(acetylthio)dodecyl 4-acetoxybenzoate
  参考文献：
  名称：

  Efficient Preparation of Novel Phenolic Surfactants for Self-Assembled Monolayers

  摘要：

  Novel molecules have been synthesized that combine the phenolic nature of tannins and self-assembling properties of surfactants. These single-chain (C-12) surfactants with potential biocompatibility have been synthesized with an omega-thiol or disulfide functionality, both commonly used anchors in self-assembly onto gold surfaces, using a modular route. Protecting groups for the phenol and thiol moieties played a key role for overcoming the challenges often associated with the purification of surfactants. The tasks of unmasking the thiol moiety and simultaneously deprotecting the acetyl protecting groups of the phenols were accomplished using sodium thiomethoxide. This modular route can be extended to synthesize other surfactants with the potential ability to form robust layers with biocompatible properties.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.844259