1-benzyl-4-phenylpiperidin-4-ylamine | 181641-49-6

• 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: 1-benzyl-4-phenylpiperidin-4-ylamine
• 英文别名: N-benzyl-4-amino-4-phenylpiperidine；1-benzyl-4-phenylpiperidin-4-amine
• CAS: 181641-49-6
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: OUVZXDBUVYNERG-UHFFFAOYSA-N

物化性质

• 沸点：
  388.0±42.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-phenylpiperidin-4-ylamine 在 palladium on activated charcoal lithium aluminium tetrahydride 、 TEA 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 196.0h， 生成 [3-(3,4-Dichlorophenyl)-3-[3-[4-(methylamino)-4-phenylpiperidin-1-yl]propyl]piperidin-1-yl]-phenylmethanone
  参考文献：
  名称：

  A reliable and efficient synthesis of SR 142801

  摘要：

  A convenient synthesis of the potent human NK-3 receptor antagonist SR 142801, (S)-(+)-N-{{3-[1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]prop-1-yl}-4-phenylpiperidin-4-yl}-N-methylacetamide [(S)-(+)(15)], is described. Improvements over the previously reported procedure are the preparation of the intermediate 5 via the novel imide 3 and subsequent reaction with the nucleophile 14, which reacts, regioselectively, at the endocyclic nitrogen. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00419-2
• 作为产物：
  描述：

  4-哌啶酮 在 盐酸 、 硫酸 、 potassium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 30.17h， 生成 1-benzyl-4-phenylpiperidin-4-ylamine
  参考文献：
  名称：

  Structure-guided design and synthesis of P1′ position 1-phenylcycloalkylamine-derived pentapeptidic BACE1 inhibitors

  摘要：

  Previously, we reported potent pentapeptidic BACE1 inhibitors with the hydroxymethylcarbonyl isostere as a substrate transition-state mimic. To improve the in vitro potency, we further reported pentapeptidic inhibitors with carboxylic acid bioisosteres at the P-4 and P-1' positions. In the current study, we screened new P-1' position 1-phenylcycloalkylamine analogs to find non-acidic inhibitors that possess double-digit nanomolar range IC50 values. An extensive structure-activity relationship study was performed with various amine derivatives at the P-1' position. The most potent inhibitor of this pentapeptide series, KMI-1830, possessing 1-phenylcyclopentylamine at the P-1' position had an IC50 value of 11.6 nM against BACE1 in vitro enzymatic assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.002

文献信息

• A Practical Synthesis of tert-Alkylamines via the Ritter Reaction with Chloroacetonitrile
  作者：Aigars Jirgensons、Valerjans Kauss、Ivars Kalvinsh、Markus R. Gold

  DOI：10.1055/s-2000-8208

  日期：——

  Ritter reaction of tertiary alcohols with chloroacetonitrile and subsequent cleavage of chloroacetyl group in the resulting chloroacetamide with thiourea is an efficient procedure for synthesis of tert-alkylamines.

  三烷基胺的高效合成步骤涉及使用氯乙腈与三级醇进行里特反应，随后在生成的氯乙酰胺中用硫脲裂解氯乙酰基团。
• UREA DERIVATIVE AND ADHESIVE-MOLECULE INHIBITOR CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP1323709A1

  公开（公告）日：2003-07-02

  Disclosed are novel urea derivatives and their medical uses, especially as adhesion molecule inhibitors useful for therapies of inflammatory diseases. The urea derivative according to the present invention has the chemical structure, for example, represented by the following Formula (35):

  揭示了新颖的尿素衍生物及其医药用途，特别是作为粘附分子抑制剂，用于治疗炎症性疾病。根据本发明的尿素衍生物具有化学结构，例如，由以下化学式（35）表示：
• 6-(4-Hydroxy-phenyl)-3-alkyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
  申请人：SANOFI

  公开号：US20130085128A1

  公开（公告）日：2013-04-04

  The present invention relates to pyrazolo[3,4-b]pyridine compounds of the formula I, in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined as indicated below. The compounds of the formula I are kinase inhibitors, and are useful for the treatment of diseases associated with diabetes and diabetic complications, such as, diabetic nephropathy, diabetic neuropathy and diabetic retinopathy, for example. The invention furthermore relates to the use of compounds of the formula I, in particular as active ingredients in pharmaceuticals, and pharmaceutical compositions comprising them.

  本发明涉及式I的吡唑并[3,4-b]吡啶化合物，其中R1、R2、R3、R4、R5、R6和R7如下所示。式I的化合物是激酶抑制剂，适用于治疗与糖尿病及糖尿病并发症相关的疾病，如糖尿病肾病、糖尿病神经病变和糖尿病视网膜病变等。此外，本发明还涉及式I的化合物的用途，特别是作为药物中的活性成分以及包含它们的药物组合物。
• Method for preparing 4-methylamino-4-phenylpiperidine
  申请人：——

  公开号：US20040181071A1

  公开（公告）日：2004-09-16

  The invention relates to a process for preparing a 4-alkoxycarbonylamino-1-benzyl-4-phenylpiperidine of formula (I) 1 via hydrolysis of 1-benzyl-4-cyano-4-phenylpiperidine (II) in acidic medium and treatment of the 1-benzyl-4-phenyl-4-piperidinecarboxamide (III) thus obtained with bromine in the presence of an alkali metal alkoxide. The invention also relates to a process for preparing 4-methylamino-4-phenylpiperidine from compound (II).

  该发明涉及一种制备4-烷氧羰基氨基-1-苄基-4-苯基哌啶的方法，通过在酸性介质中水解1-苄基-4-氰基-4-苯基哌啶（II），并将得到的1-苄基-4-苯基-4-哌啶羧酰胺（III）与溴在碱金属碱中存在的条件下处理。该发明还涉及一种从化合物（II）制备4-甲氨基-4-苯基哌啶的方法。
• (3R)-3-Amino-4-(2,4,5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy)benzothiazol-2-yl]tetrahydropyran-4-yl}butanamide as a potent dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes
  作者：Aiko Nitta、Hideaki Fujii、Satoshi Sakami、Yutaka Nishimura、Tomofumi Ohyama、Mikiya Satoh、Junko Nakaki、Shiho Satoh、Chifumi Inada、Hideki Kozono、Hiroki Kumagai、Masahiro Shimamura、Tominaga Fukazawa、Hideki Kawai

  DOI：10.1016/j.bmcl.2008.09.042

  日期：2008.10

  and 3-amino-N-(4-aryltetrahydropyran-4-yl)butanamides were synthesized and evaluated as dipeptidyl peptidase IV (DPP-IV) inhibitors. Derivatives incorporating the 6-substituted benzothiazole group showed highly potent DPP-IV inhibitory activity. Oral administration of (3R)-3-amino-4-(2,4,5-trifluorophenyl)-N-4-[6-(2-methoxyethoxy)benzothiazol-2-yl ]tetrahydropyran-4-yl}butanamide (12u) reduced blood

  合成了一系列新颖的3-氨基-N-（4-芳基-1,1-二氧噻吩-4-基）丁酰胺和3-氨基-N-（4-芳基四氢吡喃-4-基）丁酰胺并评估为二肽基肽酶IV （DPP-IV）抑制剂。掺入6-取代的苯并噻唑基团的衍生物显示出强效的DPP-IV抑制活性。（3R）-3-氨基-4-（2,4,5-三氟苯基）-N- 4- [6-（2-甲氧基乙氧基）苯并噻唑-2-基]四氢吡喃-4-基}丁酰胺的口服给药（ 12u）在口服葡萄糖耐量试验中降低了血糖偏移。