octyl adamantane-1-carboxylate

• 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: octyl adamantane-1-carboxylate
• 英文别名: octyl 1-adamantanecarboxylate；octyl 1-adamantancarboxylate；octyl adamantanecarboxylate；1-Adamantanecarboxylic acid, octyl ester
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: HABNPYGVMJNTSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  辛醇 、 1-金刚烷甲酸 在 N-butyl-2,4-dinitroanilinium p-toluenesulfonate 作用下， 以 异辛烷 为溶剂， 反应 19.0h， 以92%的产率得到octyl adamantane-1-carboxylate
  参考文献：
  名称：

  N-Butyl-2,4-dinitro-anilinium p-甲苯磺酸盐作为高活性和选择性酯化催化剂

  摘要：

  发现 N -Butyl-2,4-dinitro-anilinium p-甲苯磺酸盐( 1 ) 是一种非常活跃的酯化催化剂，可在温和条件下促进等摩尔量的羧酸和醇的缩合。该催化剂在环境温度下对羧酸和醇底物也具有高度选择性。

  DOI：

  10.1016/j.tetlet.2013.09.132

文献信息

• Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) salts
  作者：Kazuaki Ishihara、Masaya Nakayama、Suguru Ohara、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(02)00966-3

  日期：2002.10

  either carboxylic acids or alcohols are normally needed. We found that the direct condensation of equimolar amounts of carboxylic acids and alcohols could be achieved using hafnium(IV) or zirconium(IV) salts. These metal salts are highly effective as catalysts for the selective esterification of primary alcohols with carboxylic acids in the presence of secondary alcohols or aromatic alcohols. The present

  为了提高合成中的原子效率并避免产生环境废物，应避免使用化学计量的缩合试剂或过量的底物。在酯化中，通常需要过量的羧酸或醇。我们发现，使用ha（IV）或锆（IV）盐可以实现等摩尔量的羧酸和醇类的直接缩合。这些金属盐在仲醇或芳族醇的存在下作为伯醇与羧酸选择性酯化的催化剂非常有效。本发明的方法可以用于直接聚酯化并且可以适用于大规模操作。
• Bulky diarylammonium arenesulfonates as mild and extremely active dehydrative ester condensation catalysts
  作者：Akira Sakakura、Shoko Nakagawa、Kazuaki Ishihara

  DOI：10.1016/j.tet.2005.09.059

  日期：2006.1

  especially large-scale, fundamental reactions like ester condensations, are highly desirable for many reactions. Bulky diarylammonium pentafluorobenzenesulfonates and tosylates serve as extremely active dehydration catalysts for the ester condensation reaction of carboxylic acids with equimolar amounts of sterically demanding alcohols and acid-sensitive alcohols. Typically, the esterification reaction is performed

  对于许多反应，非常需要对当前化学方法更具环境友好性的替代方法，尤其是大规模的基本反应，如酯缩合。庞大的五氟苯磺酸二芳基铵盐和甲苯磺酸盐是非常有效的脱水催化剂，用于羧酸与等摩尔量的空间需求的醇和酸敏感性醇的酯缩合反应。典型地，酯化反应是在庚烷中，在1mol％催化剂的存在下，在80℃下加热进行的，而不除去水。即使在室温下，也可以在没有溶剂的情况下使用伯醇进行酯化。此外，与4-（N-间苯二甲氨基）聚苯乙烯树脂结合的五氟苯磺酸盐可以循环使用超过10次而不会损失活性。
• Open-air and solvent-free ester condensation catalyzed by sulfonic acids
  作者：Akira Sakakura、Yoshiki Koshikari、Kazuaki Ishihara

  DOI：10.1016/j.tetlet.2008.06.058

  日期：2008.8

  Ester condensation is one among the most fundamental organic transformations, and more environmentally benign alternatives to current esterification processes are needed. Under solvent-free and drying agent-free conditions, catalytic amounts of sulfonic acids promote ester condensation between an equimolar mixture of carboxylic acids and alcohols. In particular, p-toluenesulfonic acid (TsOH) and 10-camphorsulfonic

  酯缩合是最基本的有机转化之一，并且需要对当前酯化方法更环境友好的替代方法。在无溶剂和无干燥剂的条件下，催化量的磺酸促进羧酸和醇的等摩尔混合物之间的酯缩合。特别地，具有适当酸度的对甲苯磺酸（TsOH）和10-樟脑磺酸（CSA）有效催化仲醇的酯缩合而不分解。由于本方案在简单的露天条件下不需要溶剂，因此可以在相当小的设备中合成大量的酯。
• Highly Efficient Solvent-Free Condensation of Carboxylic Acids with Alcohols Catalysed by Zinc Perchlorate Hexahydrate, Zn(ClO4)2?6?H2O
  作者：G. Bartoli、J. Boeglin、M. Bosco、M. Locatelli、M. Massaccesi、P. Melchiorre、L. Sambri

  DOI：10.1002/adsc.200404171

  日期：2005.1

  Zinc perchlorate hexahydrate, Zn(ClO4)2⋅6 H2O, efficiently catalyses the esterification between nearly equimolar amounts of carboxylic acids and alcohols. The reaction works under solvent-free conditions at relatively low temperatures. Excellent results were obtained with a wide range of substrates.

  高氯酸盐锌六水合物，锌（CLO 4）2 ⋅6ħ 2 O，有效地催化几乎等摩尔量的羧酸和醇之间的酯化。该反应在相对低的温度下在无溶剂条件下进行。在多种基材上均获得了优异的结果。
• Esterification Catalysis by Pyridinium <i>p</i>-Toluenesulfonate Revisited—Modification with a Lipid Chain for Improved Activities and Selectivities
  作者：Wei Wang、Huimin Liu、Shaoyi Xu、Yong Gao

  DOI：10.1080/00397911.2012.749990

  日期：2013.11.2

  The lipid analogs of pyridinium p-toluenesulfonate (PPTS) were examined for catalysis of the condensation of an equimolar mixture of carboxylic acids and alcohols under mild conditions without removal of water. Although PPTS is a poor catalyst, the introduction of a lipid chain and nitro group significantly improved the activity of PPTS and led to selectivity at suppressing the elimination side reactions of alcohols. 2-Oleamido-5-nitro-pyridinium p-toluenesulfonate (6) is a lead catalyst that promoted various esterification reactions with yields up to 99%. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]