dodecyl 1-adamantanecarboxylate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dodecyl 1-adamantanecarboxylate
• 英文别名: 1-dodecyl 1-adamantanecarboxylate；dodecyl adamantane-1-carboxylate
• 化学式: C₂₃H₄₀O₂
• 分子量: 348.569
• InChiKey: IEIIVXJDBBBRKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  十二烷醇 、 1-金刚烷甲酸 在 十二烷基苯磺酸 作用下， 以 水 为溶剂， 反应 48.0h， 以93%的产率得到dodecyl 1-adamantanecarboxylate
  参考文献：
  名称：

  Dehydration Reactions in Water. Brønsted Acid−Surfactant-Combined Catalyst for Ester, Ether, Thioether, and Dithioacetal Formation in Water

  摘要：

  Dehydration reactions in water have been realized by a surfactant-type catalyst, dodecylbenzenesulfonic acid (DBSA). These reactions include dehydrative esterification, etherification, thioetherification, and dithioacetalization. In these reactions, DBSA and substrates form emulsion droplets whose interior is hydrophobic enough to exclude water molecules generated during the reactions. Detailed studies on the esterification revealed that the yields of esters were affected by temperature, amounts of DBSA used, and the substrates. Esters were obtained in high yields for highly hydrophobic substrates. On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained. Furthermore, chemospecific, three-component reactions under DBSA-catalyzed conditions were also found to proceed smoothly. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.

  DOI：

  10.1021/ja026241j

文献信息

• A Linear-Hyperbranched Supramolecular Amphiphile and Its Self-Assembly into Vesicles with Great Ductility
  作者：Wei Tao、Yong Liu、Binbin Jiang、Songrui Yu、Wei Huang、Yongfeng Zhou、Deyue Yan

  DOI：10.1021/ja207924w

  日期：2012.1.18

  A linear-hyperbranched supramolecular amphiphile was synthesized through the noncovalent coupling of adamantane-functionalized long alkyl chain (AD-C(n), n = 12, 18, 30) and hyperbranched polyglycerol grafted from β-cyclodextrin (CD-g-HPG) by the specific AD/CD host-guest interactions. The obtained supramolecular C(n)-b-HPGs self-assembled into unilamellar vesicles with great ductility that could be

  通过金刚烷功能化的长烷基链（AD-C(n), n = 12, 18, 30）和从β-环糊精接枝的超支化聚甘油（CD-g-HPG）的非共价偶联合成线性超支化超分子两亲物通过特定的 AD/CD 主客交互。获得的超分子 C(n)-b-HPGs 自组装成具有良好延展性的单层囊泡，在 β-CD 的竞争宿主下可以很容易地分解。
• Hydrophobic <i>N,N-</i>Diarylammonium Pyrosulfates as Dehydrative Condensation Catalysts under Aqueous Conditions
  作者：Akira Sakakura、Yoshiki Koshikari、Matsujiro Akakura、Kazuaki Ishihara

  DOI：10.1021/ol2027366

  日期：2012.1.6

  Oil-soluble N,N-diarylammonium pyrosulfates as nonsurfactant-type catalysts for the dehydrative ester condensation under aqueous conditions are described. Preheat treatment of dibasic sulfuric acid with bulky N,N-diarylamines generates water-tolerant salts of pyrosulfuric acid as active catalyst species. The present catalysts in water can also widely be applied to unusual selective esterifications and dehydrative glycosylation.
• Dehydration Reactions in Water. Brønsted Acid−Surfactant-Combined Catalyst for Ester, Ether, Thioether, and Dithioacetal Formation in Water
  作者：Kei Manabe、Shinya Iimura、Xiang-Min Sun、Shū Kobayashi

  DOI：10.1021/ja026241j

  日期：2002.10.1

  Dehydration reactions in water have been realized by a surfactant-type catalyst, dodecylbenzenesulfonic acid (DBSA). These reactions include dehydrative esterification, etherification, thioetherification, and dithioacetalization. In these reactions, DBSA and substrates form emulsion droplets whose interior is hydrophobic enough to exclude water molecules generated during the reactions. Detailed studies on the esterification revealed that the yields of esters were affected by temperature, amounts of DBSA used, and the substrates. Esters were obtained in high yields for highly hydrophobic substrates. On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained. Furthermore, chemospecific, three-component reactions under DBSA-catalyzed conditions were also found to proceed smoothly. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.