1-phenethyl-3,4-epoxypiperidine | 1309584-72-2

• 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: 1-phenethyl-3,4-epoxypiperidine
• 英文别名: 3-Phenethyl-7-oxa-3-aza-bicyclo[4.1.0]heptane；3-(2-phenylethyl)-7-oxa-3-azabicyclo[4.1.0]heptane
• CAS: 1309584-72-2
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: VPVIXOOQCRNCHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  15.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenethyl-3,4-epoxypiperidine 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (4aRS,8aRS)-4-(4-fluorophenyl)-hexahydro-6-phenethyl-2H-pyrido[4,3-b][1,4]oxazin-3(4H)-one
  参考文献：
  名称：

  High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines

  摘要：

  Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new beta-hydroxy substituted anilidopiperidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.045
• 作为产物：
  描述：

  1-(2-苯基乙基)吡啶鎓溴化物 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.42h， 生成 1-phenethyl-3,4-epoxypiperidine
  参考文献：
  名称：

  High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines

  摘要：

  Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new beta-hydroxy substituted anilidopiperidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.045

文献信息

• PROCESS FOR PRODUCING 1-SUBSTITUTED TRANS-4-(SUBSTITUTED AMINO) PIPERIDIN-3-OL
  申请人：Aikawa Toshiaki

  公开号：US20110172431A1

  公开（公告）日：2011-07-14

  A process is provided for producing a 1-substituted trans-4-(substituted amino)piperidin-3-ol represented by formula (III-1): The process includes a step of reacting a 1-substituted-3,4-epoxypiperidine represented by formula (I): with an amine compound represented by formula (II) in the presence of an inorganic lithium salt. By utilizing the process, trans-4-aminopiperidin-3-ol compounds useful as various chemical products, such as medicine intermediates, can be produced.

  提供了一种生产1-取代的反式-4-(取代氨基)哌啶-3-醇的过程，其化学式为(III-1)：该过程包括以下步骤：将一种化学式为(I)的1-取代-3,4-环氧哌啶与一种化学式为(II)的胺化合物在无机锂盐存在下反应。通过利用该过程，可以生产用途广泛的反式-4-氨基哌啶-3-醇化合物，如药物中间体等化学产品。
• METHOD FOR PRODUCING N-SUBSTITUTED-TRANS-4-AZIDOPIPERIDINE-3-OL
  申请人：Tokuda Osamu

  公开号：US20110166357A1

  公开（公告）日：2011-07-07

  An N-substituted-trans-4-azidopiperidin-3-ol represented by formula (II-1) R 1 is as defined below, which is useful as a pharmaceutical intermediate and so on, is produced by reacting an N-substituted-3,4-epoxypiperidine represented by formula (I): wherein R 1 represents an aralkyl group having 7 to 24 carbon atoms or an alkyl group having 1 to 12 carbon atoms, with sodium azide in the presence of an inorganic lithium salt.

  由下式表示的N-取代-trans-4-偶氮基哌啶-3-醇（II-1）R1如下定义，其作为制药中间体等是有用的，通过将由下式表示的N-取代-3,4-环氧哌啶（I）与氢氧化钠在无机锂盐存在下反应而制得：其中R1代表具有7至24个碳原子的芳基烷基基团或具有1至12个碳原子的烷基基团。
• PROCESS FOR PRODUCING 1-SUBSTITUTED TRANS-4-(SUBSTITUTED AMINO)PIPERIDIN-3-OL
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2351738A1

  公开（公告）日：2011-08-03

  A process for producing a 1-substituted trans-4-(substituted amino)piperidin-3-ol represented by formula (III-1): wherein R1 represents an aromatic carbocyclic group, an alkyl group having 1 to 12 carbon atoms which may be substituted with one or more aromatic carbocyclic groups, an alkenyl group having 2 to 14 carbon atoms which may be substituted with one or more aromatic carbocyclic groups, or an alkynyl group having 2 to 12 carbon atoms which may be substituted with one or more aromatic carbocyclic groups, and the like, which comprises a step of reacting a 1-substituted-3,4-epoxypiperidine represented by formula (I): with an amine compound represented by formula (II) in the presence of an inorganic lithium salt. By utilizing the process, trans-4-aminopiperidin-3-ol compounds useful as various chemical products, such as medicine intermediates, can be produced.

  一种生产式 (III-1) 所代表的 1-取代反式-4-(取代氨基)哌啶-3-醇的工艺： 其中 R1 代表芳香族碳环基团、具有 1 至 12 个碳原子且可被一个或多个芳香族碳环基团取代的烷基、具有 2 至 14 个碳原子且可被一个或多个芳香族碳环基团取代的烯基、或具有 2 至 12 个碳原子且可被一个或多个芳香族碳环基团取代的炔基等、 其中包括使式（I）代表的 1-取代-3,4-环氧哌啶反应的步骤： 与式 (II) 所代表的胺化合物反应 在无机锂盐存在下进行。利用该工艺可生产出反式-4-氨基哌啶-3-醇化合物，该化合物可用作各种化学产品，如医药中间体。
• High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines
  作者：Matthias Scheunemann、Lothar Hennig、Uta Funke、Jörg Steinbach

  DOI：10.1016/j.tet.2011.03.045

  日期：2011.5

  Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new beta-hydroxy substituted anilidopiperidines. (C) 2011 Elsevier Ltd. All rights reserved.