6-(pyrrolidin-1-yl)hexanoic acid ethyl ester

• 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: 6-(pyrrolidin-1-yl)hexanoic acid ethyl ester
• 英文别名: 6-pyrrolidino-hexanoic acid ethyl ester；6-Pyrrolidino-hexansaeure-aethylester；Ethyl 6-pyrrolidin-1-ylhexanoate
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: AXLMFEYAYCQMKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(pyrrolidin-1-yl)hexanoic acid ethyl ester 在 盐酸 、 乙醚 、 溶剂黄146 作用下， 生成 1-(6,6-diphenyl-hex-5-enyl)-pyrrolidine
  参考文献：
  名称：

  GB682160

  摘要：

  公开号：
• 作为产物：
  描述：

  四氢吡咯 、 6-溴己酸乙酯 在 Petroleum ether 作用下， 生成 6-(pyrrolidin-1-yl)hexanoic acid ethyl ester
  参考文献：
  名称：

  GB682160

  摘要：

  公开号：

文献信息

• Esters and amides of hexanoic acid substituted with tertiary amino group in terminal position and their activity as transdermal permeation enhancers
  作者：Oldřich Farsa、Pavel Dolezal、Alexandr Hrabálek

  DOI：10.2298/jsc090527034f

  日期：——

  Series of alkyl esters of 6-diethylamino-, 6-(pyrrolidin-1-yl)-, 6- (piperidin-1-yl) and 6-(morpholin-1-yl)hexanoic acids and alkylamides of 6-dimethylamino-, 6-(piperidin-1-yl) and 6-(morpholin-1-yl)hexanoic acids, containing 8-12 carbon atoms in the alkyl chain, were prepared by methods of classical organic synthesis. The appropriate secondary amine was alkylated with ethyl-6-bromohexanoate to give ester of ?-substituted hexanoic acid, except of ethyl-6-dimethylaminohexanoate (1), which was prepared by Eschweiler-Clarke methylation of 6-aminohexanoic acid followed by direct esterification with ethanol. The resulted esters of ?-substituted hexanoic acids underwent direct transesterification with long chain alkanols to yield the desired amino esters, or they were treated with long-chain alkylamines to prepare secondary amides of the appropriate heterocyclic hexanoic acids. These products were in vitro tested on their activity as transdermal permeation enhancers on the strips of the excised human skin with theophylline as the model permeant. The activity was evaluated using parameter enhancement ratio (ER), defined as the ratio between the overall amount of the permeant passing through the skin with the tested enhancer and that without tested substance. Decyl 6-(pyrrolidin- 1-yl)hexanoate (16) with ER = 30 showed the highest activity. The enhancing effects of the esters were generally better than those of the amides.

  采用经典有机合成方法制备了烷基链中含有 8-12 个碳原子的 6-二乙氨基-、6-（吡咯烷-1-基）-、6-（哌啶-1-基）和 6-（吗啉-1-基）己酸的烷基酯和 6-二甲氨基-、6-（哌啶-1-基）和 6-（吗啉-1-基）己酸的烷基酰胺系列。适当的仲胺与 6-溴己酸乙酯发生烷基化反应，得到被取代的己酸酯，但 6-二甲氨基己酸乙酯（1）除外，它是通过 6-氨基己酸的埃施韦勒-克拉克甲基化反应，然后用乙醇直接酯化制备的。生成的?-取代己酸酯直接与长链烷醇进行酯交换反应，生成所需的氨基酯，或者用长链烷胺处理，制备适当杂环己酸的仲酰胺。以茶碱为模型渗透剂，对这些产品作为透皮渗透促进剂在切除的人体皮肤条上的活性进行了体外测试。其活性是通过参数增强比（ER）来评估的，参数增强比的定义是渗透剂通过皮肤的总量与未加入受测物质的渗透剂通过皮肤的总量之比。ER=30的6-（吡咯烷-1-基）己酸癸酯（16）显示出最高的活性。酯类的增强效果普遍优于酰胺类。
• Process for the preparation of amino ketones
  申请人：BURROUGHS WELLCOME CO

  公开号：US02649444A1

  公开（公告）日：1953-08-18
• GB682160
  申请人：——

  公开号：——

  公开（公告）日：——