1-(2-噻吩-2-基乙基)哌啶-4-酮 | 92065-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-(2-噻吩-2-基乙基)哌啶-4-酮
• 英文名称: N-[2-(2-thienyl)ethyl]-4-piperidinone
• 英文别名: N-[2-(2-thienyl) ethyl]-4-piperidone；NTP；4-Piperidinone, 1-[2-(2-thienyl)ethyl]-；1-(2-thiophen-2-ylethyl)piperidin-4-one
• CAS: 92065-14-0
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: KVPQGTJHGKSEHS-UHFFFAOYSA-N

物化性质

• 沸点：
  334.7±27.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-噻吩-2-基乙基)哌啶-4-酮 在 dimsylsodium 作用下， 以 四氢呋喃 为溶剂， 生成 4-(Anilinomethyl)-1-(2-thiophen-2-ylethyl)piperidin-4-ol
  参考文献：
  名称：

  Concise and Versatile Syntheses of N-Arylalkylpiperidines as Potential Intermediates for 4-Anilidopiperidine Analgesics

  摘要：

  N-Arylalkylpiperidones and N-arylalkylspiroepoxypiperidine as potential intermediates for 4-anilidopiperidine analgesics and their structural analogues have been efficiently synthesized from the simple arylalkylamines by two and three step sequences respectively.

  DOI：

  10.3987/com-97-8056
• 作为产物：
  描述：

  1-(2-(噻吩-2-基)乙基)哌啶-4-醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到1-(2-噻吩-2-基乙基)哌啶-4-酮
  参考文献：
  名称：

  Concise and Versatile Syntheses of N-Arylalkylpiperidines as Potential Intermediates for 4-Anilidopiperidine Analgesics

  摘要：

  N-Arylalkylpiperidones and N-arylalkylspiroepoxypiperidine as potential intermediates for 4-anilidopiperidine analgesics and their structural analogues have been efficiently synthesized from the simple arylalkylamines by two and three step sequences respectively.

  DOI：

  10.3987/com-97-8056

文献信息

• An Efficient, Optimized Synthesis of Fentanyl and Related Analogs
  作者：Carlos A. Valdez、Roald N. Leif、Brian P. Mayer

  DOI：10.1371/journal.pone.0108250

  日期：——

  panel of four fentanyls in excellent yields (73-78%) along with their more commonly encountered hydrochloride and citric acid salts. The following strategy offers the opportunity for the gram-scale, efficient production of this interesting class of opioid alkaloids.

  描述了母体阿片类芬太尼及其类似物的替代和优化合成。在对每个合成步骤进行优化研究后，所展示的路线表现出高产转化，导致这些强大的镇痛药。一般的三步策略以优异的产率 (73-78%) 产生了一组四种芬太尼，以及它们更常见的盐酸盐和柠檬酸盐。以下策略为克级、高效生产这一类有趣的阿片类生物碱提供了机会。
• Improved method for the total synthesis of thiofentanyl
  作者：M. J. Taghizadeh、S. J. Hosseini、S. M. Moosavi、H. Parsa

  DOI：10.1002/jhet.3983

  日期：——

  Thiofentanyl is a potent analgesic and anesthetic drug that belongs to the microreceptor agonist group and is mainly used in animal's anesthesia. We present an optimized synthesis route for synthesis of thiofentanyl using nanocatalysts such as MCM-41-SO3H and SBA-15-Ph-PrSO3H as green, heterogeneous and recyclable catalysts according to the strategy. The intermediate 2-(thiophen-2-yl) ethyl methanesulfonate

  硫芬太尼是一种强效镇痛麻醉药，属于微受体激动剂组，主要用于动物的麻醉。根据该策略，我们提出了使用 MCM-41-SO 3 H 和 SBA-15-Ph-PrSO 3 H等纳米催化剂作为绿色、多相和可回收催化剂合成硫芬太尼的优化合成路线。使用甲磺酰氯将醇官能团转化为甲磺酸酯离去基团后，很容易得到中间体甲磺酸2-(噻吩-2-基)乙酯( 1 )(97%收率)。市售4-的烷基化哌啶酮一水合物盐酸盐与 2-(噻吩-2-基) 甲磺酸乙酯在相转移催化剂存在下进行，得到 N-[2-(2-噻吩基)乙基]-4-哌啶酮 ( 2 )，收率为90 % . 然后， N -[2-(2-噻吩基)乙基]-4-哌啶酮与苯胺在 MCM-41-SO 3 H 催化剂存在下反应，得到亚胺衍生物，亚胺衍生物用三乙酰氧基硼氢化钠还原为N -苯基-1-( 2-(噻吩-2-基)乙基)哌啶-4-胺 (ANTP) ( 4 )，产率为 80%。最后使用丙酰氯将
• Pyrrolylaminopiperidines
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US04452803A1

  公开（公告）日：1984-06-05

  This invention relates to pyrrolylaminopiperidines and related compounds of the formula ##STR1## where R is hydrogen, loweralkyl, Arloweralkyl, cycloalkylloweralkyl, loweralkenyl and thienylloweralkyl; R.sub.1 is lower alkyl, hydrogen, loweralkylcarbonyl, loweralkoxycarbonyl, loweralkylthiocarbonyl of the formula ##STR2## cyano, loweralkylaminocarbonyl, diloweralkylaminocarbonyl, cycloalkylcarbonyl, cycloalkylloweralkylcarbonyl and loweralkenylcarbonyl; R.sub.2 is hydrogen, halogen and methyl; and the pharmaceutically acceptable acid addition salts thereof.

  本发明涉及式子为##STR1##的吡咯基氨基哌啶及其相关化合物，其中R是氢、低碳基、Ar低碳基、环烷基低碳基、低烯基和噻吩基低碳基；R.sub.1是低碳基、氢、低碳基羰基、低碳基氧羰基、低碳基硫羰基的式子##STR2##、氰基、低碳基氨基羰基、二低碳基氨基羰基、环烷基羰基、环烷基低碳基羰基和低烯基羰基；R.sub.2是氢、卤素和甲基；以及其药用酸盐。
• Pyrrolylaminopiperidines, compositions thereof and methods of use
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04546105A1

  公开（公告）日：1985-10-08

  This invention relates to pyrrolylaminopiperidines and related compounds of the formula ##STR1## where R is hydrogen, loweralkyl, Arloweralkyl, cycloalkylloweralkyl, loweralkenyl and thienylloweralkyl; R.sub.1 loweralkyl, hydrogen, loweralkylcarbonyl, loweralkoxycarbonyl, loweralkylthiocarbonyl of the formula ##STR2## cyano, loweralkylaminocarbonyl, diloweralkylaminocarbonyl, cycloalkylcarbonyl, cycloalkylloweralkylcarbonyl and loweralkenylcarbonyl; R.sub.2 is hydrogen, halogen and methyl; and the pharmaceutically acceptable acid addition salts thereof.

  本发明涉及公式##STR1##中的吡咯基氨基哌啶及其相关化合物，其中R为氢、低碳基、Ar低碳基、环烷基低碳基、低烯基和噻吩基低碳基；R.sub.1为低碳基、氢、低碳基羰基、低碳酸甲酯基、低碳基硫代甲酰基的公式##STR2##、氰基、低碳基氨基羰基、二低碳基氨基羰基、环烷基羰基、环烷基低碳基羰基和低烯基羰基；R.sub.2为氢、卤素和甲基；以及其药学上可接受的酸加成盐。
• Nitrogen-containing spirocycles
  申请人：MERCK & CO. INC.

  公开号：EP0431943A2

  公开（公告）日：1991-06-12

  Spirocydes of general structural formula are Class III antiarrhythmic agents. Jouve, 18, rue Saint-Denis, 75001 PARIS

  一般结构式为 是 III 类抗心律失常药物。Jouve, 18, rue Saint-Denis, 75001 PARIS