2-phenylethyl adamantane-1-carboxylate | 959304-95-1

• 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: 2-phenylethyl adamantane-1-carboxylate
• 英文别名: adamantane-1-carboxylic acid phenethyl ester；1-Adamantanecarboxylic acid, 2-phenylethyl ester
• CAS: 959304-95-1
• 化学式: C₁₉H₂₄O₂
• 分子量: 284.398
• InChiKey: LSAWTBDIUIUZAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  苯乙醇 、 1-金刚烷甲酸 在 N-甲基吗啉 、 C₁₆H₂₀N₅O₂⁽¹⁺⁾*Cl^(1-) 、 N,N-二甲基乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以83%的产率得到2-phenylethyl adamantane-1-carboxylate
  参考文献：
  名称：

  4-(二甲氨基)吡啶作为酰基转移催化剂的三嗪二酮脱水缩合试剂的研制

  摘要：

  开发了一种新的基于三嗪二酮的试剂 ( N , N'-二烷基)三嗪二酮-4-(二甲氨基)吡啶 (ATD-DMAP)，用于操作简单的羧酸脱水缩合。该试剂包含一个ATD核和作为离去基团的DMAP，它被释放到反应体系中以加速酰基转移反应。在胺碱存在下将 ATD-DMAP 添加到羧酸和醇的混合物中，在室温下迅速形成相应的酯。此外，使用 ATD-DMAP 使羧酸和胺之间的脱水缩合以高产率进行。

  DOI：

  10.1039/d1ob00450f

文献信息

• Microwave-Assisted Ester Formation Using <i>O</i>-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration
  作者：Alessandra Chighine、Stefano Crosignani、Marie-Claire Arnal、Mark Bradley、Bruno Linclau

  DOI：10.1021/jo900476y

  日期：2009.7.3

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.
• Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst
  作者：Jie Liu、Hikaru Fujita、Masanori Kitamura、Daichi Shimada、Munetaka Kunishima

  DOI：10.1039/d1ob00450f

  日期：——

  the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative

  开发了一种新的基于三嗪二酮的试剂 ( N , N'-二烷基)三嗪二酮-4-(二甲氨基)吡啶 (ATD-DMAP)，用于操作简单的羧酸脱水缩合。该试剂包含一个ATD核和作为离去基团的DMAP，它被释放到反应体系中以加速酰基转移反应。在胺碱存在下将 ATD-DMAP 添加到羧酸和醇的混合物中，在室温下迅速形成相应的酯。此外，使用 ATD-DMAP 使羧酸和胺之间的脱水缩合以高产率进行。