N-(1-benzylpiperidin-4-ylidene)-1-phenylmethanamine | 119198-98-0

• 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: N-(1-benzylpiperidin-4-ylidene)-1-phenylmethanamine
• 英文别名: 1-Benzyl-4-benzyliminopiperidine；N,1-dibenzylpiperidin-4-imine
• CAS: 119198-98-0
• 化学式: C₁₉H₂₂N₂
• 分子量: 278.397
• InChiKey: XPQITDHWKMRSTP-UHFFFAOYSA-N

物化性质

• 沸点：
  395.1±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-benzylpiperidin-4-ylidene)-1-phenylmethanamine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-benzylpiperidin-4-yl-benzylamine
  参考文献：
  名称：

  A new series of M3 muscarinic antagonists based on the 4-amino-piperidine scaffold

  摘要：

  A series of 4-amino-piperidine containing molecules have been synthesized and structure-affinity relationship toward the M3-muscarinic receptor has been investigated. Chemical modulations provided molecules with K-i for the human M3-R up to 1 nM with variable selectivity (3- to 40-fold) over the human M2-R. Compounds 2 (pA(2) = 8.3, 8.6) demonstrates in vitro on guinea pig bladder and ileal strips potent anticholinergic properties and tissue selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00487-0
• 作为产物：
  描述：

  N-苄基哌啶酮 、 苄胺 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以97%的产率得到N-(1-benzylpiperidin-4-ylidene)-1-phenylmethanamine
  参考文献：
  名称：

  四种新颖的天然药物启发的支架用于药物开发的合成。

  摘要：

  受许多生物活性天然产物（如组织毒素）的新型螺旋结构的启发，已设计了一系列新型螺旋支架，并开发了稳健的合成方法。脚手架是现成的构建基块，可以轻松制备成5-20克的规模。它们含有两个氨基基团（一个受Boc保护的氨基基团），并且使用酰胺形成或还原性胺化步骤进行了设计，可轻松转换成铅生成库。以RCM为关键步骤，完成了1,9-二氮杂螺[5.5]十一烷和3,7-二氮杂螺[5.6]十二烷环的合成。据报道，有一种简单的后处理程序可以去除高度着色的钌残留物。1,8-二氮杂螺[4.的合成。5]癸烷支架是通过在酸性条件下使用溴介导的相应的4-氨基丁烯中间体的5-内基环化来实现的。这是要报道的这类环化反应的第一个例子。提出了一种新的机理，涉及从最初形成的溴离子到相邻氮原子的溴转移反应，这是这种反应在“正常”溴化条件下失败的原因。据报道，1-酰基-1，9-二氮杂螺[5.5]十一烷的异常重新排列为相应的9-酰基-1，9-二氮杂螺[5

  DOI：

  10.1021/jo802456w

文献信息

• A simple and convenient route to 1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridines
  作者：Elena L Gaidarova、Anatoly A Borisenko、Taras I Chumakov、Andrey V Mel'nikov、Ivan S Orlov、Galina V Grishina

  DOI：10.1016/s0040-4039(98)01662-1

  日期：1998.10

  A simple and convenient synthetic approach to the new series of 1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridines 1a-j has been developed. This was achieved via a one-pot process combining metalated 4-piperidinonimine alkylation and intramolecular cyclization.

  已经开发了一种简单方便的合成方法，用于新系列的1,2,3,4,5,6,7,8-八氢-1,6-萘啶1a-j。这是通过结合金属化的4-哌啶亚胺烷基化和分子内环化的一锅法实现的。
• Synthesis of Four Novel Natural Product Inspired Scaffolds for Drug Discovery
  作者：Ian D. Jenkins、Fabienne Lacrampe、Justin Ripper、Lilian Alcaraz、Phuc Van Le、George Nikolakopoulos、Priscila de Almeida Leone、Rodney H. White、Ronald J. Quinn

  DOI：10.1021/jo802456w

  日期：2009.2.6

  Inspired by the novel spiro structures of a number of bioactive natural products such as the histrionicotoxins, a series of novel spiro scaffolds have been designed and robust syntheses developed. The scaffolds are ready-to-use building blocks and can be easily prepared on a 5−20 g scale. They contain two amino groups (one Boc-protected) and have been designed for ease of conversion to a lead generation

  受许多生物活性天然产物（如组织毒素）的新型螺旋结构的启发，已设计了一系列新型螺旋支架，并开发了稳健的合成方法。脚手架是现成的构建基块，可以轻松制备成5-20克的规模。它们含有两个氨基基团（一个受Boc保护的氨基基团），并且使用酰胺形成或还原性胺化步骤进行了设计，可轻松转换成铅生成库。以RCM为关键步骤，完成了1,9-二氮杂螺[5.5]十一烷和3,7-二氮杂螺[5.6]十二烷环的合成。据报道，有一种简单的后处理程序可以去除高度着色的钌残留物。1,8-二氮杂螺[4.的合成。5]癸烷支架是通过在酸性条件下使用溴介导的相应的4-氨基丁烯中间体的5-内基环化来实现的。这是要报道的这类环化反应的第一个例子。提出了一种新的机理，涉及从最初形成的溴离子到相邻氮原子的溴转移反应，这是这种反应在“正常”溴化条件下失败的原因。据报道，1-酰基-1，9-二氮杂螺[5.5]十一烷的异常重新排列为相应的9-酰基-1，9-二氮杂螺[5
• Two-step synthesis of new 1,2,4,5-tetrahydrospiro-[3<i>H</i>-2-benzazepine-3,4′-piperidines] from 4-iminopiperidines
  作者：Palma R. Alirio、Sandra Salas、Vladimir Kouznetsov、Elena Stashenko、Montenegro N. Gisela、Fontela G. Angel

  DOI：10.1002/jhet.5570380405

  日期：2001.7

  New spiro[3H-2-benzazepine-3,4′-piperidines] and their precursors, N-substituted 4-allyl-4-N-benzyl-aminopiperidines, have been prepared as potential psychotic agents from readily available 4-iminopiperidines, by a sequence of reactions that included nucleophilic addition of Grignard reagents and Bronsted acid-mediated intramolecular cyclisation. Some of the compounds prepared have been tested in albine

  新的螺[3 H -2-苯并ze庚因-3,4'-哌啶]及其前体N-取代的4-烯丙基-4- N-苄基-氨基哌啶已从容易获得的4-亚氨基哌啶中制备为潜在的精神病药物，通过一系列反应，包括亲核添加格氏试剂和布朗斯台德酸介导的分子内环化反应。已经在白化病小鼠中测试了所制备的某些化合物的自发运动活性。通过ir和1 H nmr光谱学和cg-ms光谱对所有制备的化合物进行表征。
• 8-METHOXYQUINOLONECARBOXYLIC ACID DERIVATIVE
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0677522A1

  公开（公告）日：1995-10-18

  An 8-methoxyquinolonecarboxylic acid derivative represented by general formula (I), and optical isomers, pharmaceutically acceptable salts and hydrates thereof, wherein R₁ represents hydrogen, lower alkyl, phenylalkyl or an in vivo hydrolyzable ester residue; R₂ represents hydrogen or methyl; and n represents an integer of 0 or 1. This derivative has a wide antimicrobial spectrum based on the activity potentiated in vitro and in vivo against gram-positive bacteria while retaining the potent antibacterial activity of the conventional quinolonecarboxylate bactericides against gram-negative bacteria. Since it scarcely has problematic side effects and is reduced in toxicity, it is promising as a bactericide having more excellent clinical effects.

  通式(I)代表的 8-甲氧基喹啉羧酸衍生物及其光学异构体、药学上可接受的盐和水合物，其中 R₁ 代表氢、低级烷基、苯基烷基或体内可水解的酯残基；R₂ 代表氢或甲基；n 代表 0 或 1 的整数。根据体外和体内对革兰氏阳性菌的增效活性，这种衍生物具有广泛的抗菌谱，同时保留了传统喹啉羧酸盐杀菌剂对革兰氏阴性菌的强效抗菌活性。由于它几乎没有副作用，毒性也较低，因此有望成为一种临床效果更佳的杀菌剂。
• 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。