2-(1-adamantyl)-3-hydroxybutyric acid | 344445-93-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-(1-adamantyl)-3-hydroxybutyric acid
• 英文别名: 2-(1-adamantyl)-3-hydroxybutanoic acid
• CAS: 344445-93-8
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: BOIIPHUFZOSXAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-adamantyl)-3-hydroxybutyric acid 在 氯化亚砜 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Adamantyl-β-butyrolactones: synthesis and ring-opening reactions

  摘要：

  2-(1-Adamantyl)-beta-butyrolactones 3a and 3b were synthesized using very common peptide coupling reagents under mild conditions and their ring-opening reactions were then studied. These novel lactones showed pronounced stability and were resistant to cleavage upon acidic water extraction and column chromatographic purification. The adamantane moiety plays an important function in lowering the lactone reactivity by protecting the electrophilic sites on the four membered ring via steric hindrance. However under certain conditions, both O-C(carbonyl) and O-C(alkyl) bond-cleavage ring-opening reactions were observed. Bond-cleavage at physiological temperature makes these novel lactones especially noteworthy. Novel adamantyl-beta-butyrolactones have a potential to act as biomembrane soluble amphiphiles that might exhibit a combination of stability and biological activity with the latter hopefully predominating. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.102
• 作为产物：
  描述：

  1-金刚烷乙酸 、 乙醛 生成 2-(1-adamantyl)-3-hydroxybutyric acid
  参考文献：
  名称：

  SASAKI, TADASHI;SHIMIZU, KAZUO;OHNO, MASATOMI, CHEM. AND PHARM. BULL., 1984, 32, N 4, 1433-1440

  摘要：

  DOI：

文献信息

• Hydrolysis and retro-aldol cleavage of ethyl threo-2-(1-adamantyl)-3-hydroxybutyrate: competing reactions
  作者：Bishwajit Ganguly、Manoj K. Kesharwani、Marija Matković、Nikola Basarić、Ajeet Singh、Kata Mlinarić-Majerski

  DOI：10.1002/poc.1793

  日期：2011.7

  hydrolysis and the retro‐aldol reaction for 1 and 4 were investigated using DFT calculations in the both gas and solvent phase. The calculated results in the solvent phase at B3LYP/6–31 + G* level revealed that the formation of retro‐aldol products is kinetically preferred over the hydrolysis of threo‐ester 1 in the presence of a base. However, the parent ester 4 showed that the retro‐aldol process is less

  通过实验和计算研究了苏式-2-（1-金刚烷基）-3-羟基丁酸乙酯（3）和母体酯3-羟基丁酸乙酯（4）的水解。用2 M NaOH水解苏糖1时，主要观察到逆醛醇产物，而水解产物的含量很少。当与母体3-羟基丁酸乙酯（4）在相同条件下进行反应时，仅观察到水解产物。竞争途径，即1和4的水解和逆醛醇反应在气相和溶剂相中均使用DFT计算法进行了研究。溶剂相中B3LYP / 6–31 + G *含量的计算结果表明，在碱存在下，逆醛醇产物的形成在动力学上优于苏糖1的水解。但是，母体酯4表明，在类似条件下，逆醛醇缩合工艺不如水解工艺受青睐。叔丁基在基团上进行的计算进一步支持了庞大的金刚烷基对增强苏--2-（1-金刚烷基）-3-羟基丁酸乙酯（1）水解的激活屏障所施加的空间效应。α3-羟基丁酸乙酯的碳原子（7）。版权所有©2010 John Wiley＆Sons，Ltd.
• Adamantyl-β-butyrolactones: synthesis and ring-opening reactions
  作者：Marija Matković、Krešimir Molčanov、Robert Glaser、Kata Mlinarić-Majerski

  DOI：10.1016/j.tet.2012.07.102

  日期：2012.10

  2-(1-Adamantyl)-beta-butyrolactones 3a and 3b were synthesized using very common peptide coupling reagents under mild conditions and their ring-opening reactions were then studied. These novel lactones showed pronounced stability and were resistant to cleavage upon acidic water extraction and column chromatographic purification. The adamantane moiety plays an important function in lowering the lactone reactivity by protecting the electrophilic sites on the four membered ring via steric hindrance. However under certain conditions, both O-C(carbonyl) and O-C(alkyl) bond-cleavage ring-opening reactions were observed. Bond-cleavage at physiological temperature makes these novel lactones especially noteworthy. Novel adamantyl-beta-butyrolactones have a potential to act as biomembrane soluble amphiphiles that might exhibit a combination of stability and biological activity with the latter hopefully predominating. (C) 2012 Elsevier Ltd. All rights reserved.
• SASAKI, TADASHI;SHIMIZU, KAZUO;OHNO, MASATOMI, CHEM. AND PHARM. BULL., 1984, 32, N 4, 1433-1440
  作者：SASAKI, TADASHI、SHIMIZU, KAZUO、OHNO, MASATOMI

  DOI：——

  日期：——