(±)-trans-1-benzyl-4-(diallylamino)-3-hydroxypiperidine

• 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: (±)-trans-1-benzyl-4-(diallylamino)-3-hydroxypiperidine
• 英文别名: (±)-trans-N-benzyl-4-(diallylamino)-3-hydroxypiperidine；(3S,4S)-1-benzyl-4-[bis(prop-2-enyl)amino]piperidin-3-ol
• 化学式: C₁₈H₂₆N₂O
• 分子量: 286.417
• InChiKey: KOVBFPGFCQBOLJ-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲氧基乙酰氯 、 (±)-trans-1-benzyl-4-(diallylamino)-3-hydroxypiperidine 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以87%的产率得到(±)-trans-1-benzyl-4-(diallylamino)-3-methoxyacetoxy-piperidine
  参考文献：
  名称：

  Highly selective chemoenzymatic synthesis of enantiopure orthogonally protected trans-3-amino-4-hydroxypiperidines

  摘要：

  Optically pure orthogonally protected trans-3-amino-4-hydroxypiperidines have been easily prepared from (+/-)-1-benzy1-3,4-epoxypiperidine. The key steps are a regioselective epoxide ring-opening with diallylamine and the enzymatic resolution of the resulting aminoalcohol. It is remarkable the high enantioselectivity obtained with Candida antarctica lipase B in the acetylation of (+/-)-trans-1-benzyl-3-(diallylamino)-4-hydroxypiperidine. The versatility of the protecting groups is showed in the subsequent transformations performed in relation to the assignment of the absolute configuration of the products. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.014
• 作为产物：
  描述：

  二烯丙基胺 、 3-苄基-7-噁-3-氮杂双环4.1.0庚烷 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以85%的产率得到(±)-trans-1-benzyl-4-(diallylamino)-3-hydroxypiperidine
  参考文献：
  名称：

  Highly selective chemoenzymatic synthesis of enantiopure orthogonally protected trans-3-amino-4-hydroxypiperidines

  摘要：

  Optically pure orthogonally protected trans-3-amino-4-hydroxypiperidines have been easily prepared from (+/-)-1-benzy1-3,4-epoxypiperidine. The key steps are a regioselective epoxide ring-opening with diallylamine and the enzymatic resolution of the resulting aminoalcohol. It is remarkable the high enantioselectivity obtained with Candida antarctica lipase B in the acetylation of (+/-)-trans-1-benzyl-3-(diallylamino)-4-hydroxypiperidine. The versatility of the protecting groups is showed in the subsequent transformations performed in relation to the assignment of the absolute configuration of the products. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.014

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。
• 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。
• Highly selective chemoenzymatic synthesis of enantiopure orthogonally protected trans-3-amino-4-hydroxypiperidines
  作者：Ángela Villar-Barro、Vicente Gotor、Rosario Brieva

  DOI：10.1016/j.tet.2015.07.014

  日期：2015.9

  Optically pure orthogonally protected trans-3-amino-4-hydroxypiperidines have been easily prepared from (+/-)-1-benzy1-3,4-epoxypiperidine. The key steps are a regioselective epoxide ring-opening with diallylamine and the enzymatic resolution of the resulting aminoalcohol. It is remarkable the high enantioselectivity obtained with Candida antarctica lipase B in the acetylation of (+/-)-trans-1-benzyl-3-(diallylamino)-4-hydroxypiperidine. The versatility of the protecting groups is showed in the subsequent transformations performed in relation to the assignment of the absolute configuration of the products. (C) 2015 Elsevier Ltd. All rights reserved.