3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one | 136423-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one
• 英文别名: 3-phenethylpiperidine-2-one；3-(2'-phenyl)ethyl piperid-2-one；3-(2-Phenylethyl)piperidin-2-one
• CAS: 136423-40-0
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: VEKXOGVOKSSHTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以89%的产率得到3-phenethylpiperidine-2-thione
  参考文献：
  名称：

  A One-Pot Bicycloannulation Method for the Synthesis of Tetrahydroisoquinoline Systems

  摘要：

  A highly effective method for the synthesis of the core indolo[2,3-a]quinolizidine skeleton found in yohimbine is described. The reaction of N-monosubstituted thioamides with bromoalkenoyl chlorides furnishes thioisomunchnones as transient 1,3-dipoles that undergo ready intramolecular cycloaddition across the tethered pi-bond to give thio-bicycloannulated products in a one-pot operation. The stereochemical outcome of the intramolecular reaction is the consequence of an endo cycloaddition of the neighboring-bond across the transient thioisomunchnone dipole. A major limitation of the method is that when a hydrogen is present in the alpha-position of the thioamide the initially formed thio-N-acyliminium ion undergoes proton loss to produce a S ,N-ketene acetal at a faster rate than dipole formation. Treatment of tetrahydro-beta-carboline-1-thione with 2-bromooct-7-enoyl chloride followed by reductive removal of sulfur from the cycloadduct resulted in the formation of (+/-)-alloyahimbanone. Attempts to cycloadd the thioisomunchnone dipole across several nucleophilic-bonds failed, and instead, products derived from cyclization of the pi-bond onto the initially formed thio-N-acyliminium ion were formed. The resulting N,S-ketals were further converted into several tetrahydroisoquinoline alkaloids in good yield.

  DOI：

  10.1021/jo991742h
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 25.0~60.0 ℃ 、100.0 kPa 条件下， 生成 3,4,5,6-tetrahydro-3-(2-phenylethyl)pyridin-2-one
  参考文献：
  名称：

  10.24820/ark.5550190.p012.235

  摘要：

  DOI：

  10.24820/ark.5550190.p012.235

文献信息

• Piperidine derivatives
  申请人：Shell Research Limited

  公开号：US05190958A1

  公开（公告）日：1993-03-02

  The invention provides piperidine derivatives of the general formula ##STR1## or an acid-addition salt or metal salt complex thereof, in which R represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, arylcarbonyl, heterocyclyl or heterocyclyloxy group; R.sup.1 represents an optionally substituted alkyl, phenyl, benzyl or cycloalkyl group; R.sup.2 represents a hydrogen atom or an optionally substituted alkyl group; one of W and X represents --CH.sub.2 --, --CH.sub.2 CH.sub.2 -- or --O--, the other of W and X being --CH.sub.2 -- or --CH.sub.2 CH.sub.2 or X represents a single chemical bond; m is 0 or 1 and n represents an integer from 0 to 3; processes for their preparation; compositions containing such compounds and their use as fungicides.

  该发明提供了一般式##STR1##的哌啶衍生物，或其酸加合盐或金属盐络合物，其中R代表氢原子或可选择取代的烷基、烯基、炔基、烷氧基、环烷基、芳基、芳基甲酰基、杂环烷基或杂环氧基；R.sup.1代表可选择取代的烷基、苯基、苄基或环烷基；R.sup.2代表氢原子或可选择取代的烷基；W和X中的一个代表--CH.sub.2 --、--CH.sub.2 CH.sub.2 --或--O--，另一个为--CH.sub.2 --或--CH.sub.2 CH.sub.2 或X代表一个单一的化学键；m为0或1，n为0到3的整数；其制备方法；含有这种化合物的组合物以及它们作为杀菌剂的用途。
• Salas, Marisa; Joule, John A., Journal of Chemical Research, Miniprint, 1990, # 3, p. 664 - 673
  作者：Salas, Marisa、Joule, John A.

  DOI：——

  日期：——
• US5190958A
  申请人：——

  公开号：US5190958A

  公开（公告）日：1993-03-02
• A One-Pot Bicycloannulation Method for the Synthesis of Tetrahydroisoquinoline Systems
  作者：Albert Padwa、L. Scott Beall、Todd M. Heidelbaugh、Bing Liu、Scott M. Sheehan

  DOI：10.1021/jo991742h

  日期：2000.5.1

  A highly effective method for the synthesis of the core indolo[2,3-a]quinolizidine skeleton found in yohimbine is described. The reaction of N-monosubstituted thioamides with bromoalkenoyl chlorides furnishes thioisomunchnones as transient 1,3-dipoles that undergo ready intramolecular cycloaddition across the tethered pi-bond to give thio-bicycloannulated products in a one-pot operation. The stereochemical outcome of the intramolecular reaction is the consequence of an endo cycloaddition of the neighboring-bond across the transient thioisomunchnone dipole. A major limitation of the method is that when a hydrogen is present in the alpha-position of the thioamide the initially formed thio-N-acyliminium ion undergoes proton loss to produce a S ,N-ketene acetal at a faster rate than dipole formation. Treatment of tetrahydro-beta-carboline-1-thione with 2-bromooct-7-enoyl chloride followed by reductive removal of sulfur from the cycloadduct resulted in the formation of (+/-)-alloyahimbanone. Attempts to cycloadd the thioisomunchnone dipole across several nucleophilic-bonds failed, and instead, products derived from cyclization of the pi-bond onto the initially formed thio-N-acyliminium ion were formed. The resulting N,S-ketals were further converted into several tetrahydroisoquinoline alkaloids in good yield.