4-(4-methyl-1-piperidinyl)-6-(2-naphthyl)-2-oxo-2H-pyran-3-carbonitrile | 518308-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(4-methyl-1-piperidinyl)-6-(2-naphthyl)-2-oxo-2H-pyran-3-carbonitrile
• 英文别名: 4-(4-Methylpiperidin-1-yl)-6-naphthalen-2-yl-2-oxopyran-3-carbonitrile
• CAS: 518308-81-1
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: KHSRMTWDCJVGOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-二苄氧基丙酮 、 4-(4-methyl-1-piperidinyl)-6-(2-naphthyl)-2-oxo-2H-pyran-3-carbonitrile 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以70%的产率得到6-(4-Methylpiperidin-1-yl)-4-naphthalen-2-yl-3-phenylmethoxy-2-(phenylmethoxymethyl)benzonitrile
  参考文献：
  名称：

  A novel strategy for the expeditious synthesis of aryl-tethered highly congested 2-hydroxybenzyl alcohols from 2-pyranones

  摘要：

  An efficient and simple synthesis of highly congested 2-benzyloxy-3-benzyloxymethyl-5-sec-aminobiphenyl-4-carbonitriles 3a-e has been delineated through base catalyzed ring transformation of 6-aryl-4-sec-amino-2H-pyran-2-one-3-carbonitriles 1 by 1,3-bisbenzyloxypropan-2-one 2. Debenzylation of both the O-benzyl groups of 3a-e with boron trichloride provided the corresponding diols, 2-hydroxy-3-hydroxymethyl-5-sec-aminobiphenyl-4-carbonitriles 4a-e in very good yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.082
• 作为产物：
  描述：

  4-甲基哌啶 、 4-(methylthio)-6-(naphthalen-2-yl)-2-oxo-2H-pyran-3-carbonitrile 以68%的产率得到4-(4-methyl-1-piperidinyl)-6-(2-naphthyl)-2-oxo-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  Synthesis of Aminonicotinonitriles and Diaminopyridines through Base-Catalyzed Ring Transformation of 2H-Pyran-2-ones

  摘要：

  An efficient and convenient synthesis of 2-amino-6-aryl-4-methylsulfanylnicotinonitriles (2), 2-amino-6-aryl-4-substituted-aminonicotinonitriles (4), and 2-amino-6-aryl-4-substituted-aminopyridines (6) has been delineated and illustrated through base-catalyzed ring transformation of 6-aryl-3-cyano-4-methylsulfanyl/substituted-amino-2H-pyran-2-ones (1, 3, and 5) with cyanamide and ammonium carbonate separately.

  DOI：

  10.1021/jo0204496

文献信息

• Synthesis of bicyclic biaryls as glucose-6-phosphatase inhibitors
  作者：Farhanullah、Brajendra K Tripathi、Arvind K Srivastava、Vishnu Ji Ram

  DOI：10.1016/j.bmc.2003.12.028

  日期：2004.3

  3-dihydrobenzo[b]thiophene-4-carbonitriles (3a-e), 8-(1-naphthyl)-6-s-amino-isothiochroman-5-carbonitriles (6a-d), 4-(1-naphthyl)-2-s-aminobezocycloalkene-1-carbonitriles (6e-j), 8-naphthyl-6-s-amino-2-ethyl-1,2,3,4-tetrahydro-isoquinoline-5-carbonitrle (6k-n), 1-naphthyl-3-s-amino-10H-9-thia-phenantherene-4-carbonitriles (8a-e) and 1-(1-naphthyl)-3-s-amino-9,10-dihydrophenantherene-4-carbonitriles

  联芳基，7-萘-5-s-氨基-2,3-二氢苯并[b]噻吩-4-甲腈（3a-e），8-（1-萘基）-6-s-氨基-异硫代苯并-5-甲腈（6a-d），4-（1-萘基）-2-s-氨基苯并环烯-1-腈（6e-j），8-萘基-6-s-氨基-2-乙基-1,2,3,4 -四氢-异喹啉-5-腈（6k-n），1-萘-3-s-氨基-10H-9-噻吩菲并-4-腈（8a-e）和1-（1-萘基）-3通过6-萘基-3-氰基-4-s-氨基-2H-吡喃-2-酮的碳负离子诱导的环转化反应制备了-s-氨基-9,10-二氢菲蒽-4-腈（8f-i） （1）来自相应的酮（2、5和7）。已经评估了这些化合物的葡萄糖-6磷酸酶抑制活性，并且仅6a，c，j，m，c，d，h显示出对葡萄糖-6磷酸酶的显着抑制。
• Base dependent purported synthesis of congested 2-aminobenzylamines and tetrahydro-2-oxoquinazolines from 2-pyranones
  作者：Farhanullah、Farhana Samrin、Vishnu Ji Ram

  DOI：10.1016/j.tet.2008.12.041

  日期：2009.2

  An expeditious and concise synthesis of highly congested 2-amino-3-aminomethyl-5-methylsulfanyl/-sec-aminobiphenyl-4-carbonitrile 4 and 1-tert-butoxycarbonyl-6-sec-amino-8-aryl-5-cyano-2-oxo-1,2,3, 4-tetrahydroquinazoline 5 has been delineated through base catalyzed ring transformation of 6-aryl-4-methylsulfanyl/-sec-amino-2H-pyran-2-one-3-carbonitrile 1 with 1,3-bis(tert-butoxycarbonylamino)-2-propanone 2, followed by TFA catalyzed hydrolysis of the intermediate [3-tert-butoxycarbonyl-aminomethyl-4-cyano-5-methylsulfanyl/-sec-aminobiphenyl-2-yl]carbamic acid tert-butyl ester 3 in moderate yield. The mechanism of formation of 5 has been established through isolation and transformation of the intermediate 3 to the 1-tert-butoxycarbonyl-6-sec-amino-8-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydroquinazoline. (C) 2009 Elsevier Ltd. All rights reserved.
• A novel route for the synthesis of highly congested aryl-tethered 2-aminobenzylamines through ring transformation of 2-pyranones
  作者：Farhanullah、Farhana Samrin、Vishnu Ji Ram

  DOI：10.1016/j.tetlet.2007.03.038

  日期：2007.4

  An innovative and efficient synthesis of highly congested 2-amino-3-aminomethyl-5-methylsulfanyl/sec-aminobiphenyl-4-carbonitriles 4 has been delineated through base catalyzed ring transformation of 6-aryl-4-methylsulfanyl/sec-amino-2H-pyran-2-one-3-carbonitriles 1 with Boc-protected 1,3-diamino-2-propanone 2, followed by TFA catalyzed hydrolysis of the intermediate [3-tert-butoxycarbonylaminomethyl-4-cyano-5-methylsulfanyl/sec-aminobiphenyl-2-yl]carbamic acid tert-butyl ester 3 in moderate yields as the TFA salts. (c) 2007 Elsevier Ltd. All rights reserved.