4-氧代-2-苯基-3,4-二氢吡啶-1(2H)-羧酸苄酯 | 126378-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氧代-2-苯基-3,4-二氢吡啶-1(2H)-羧酸苄酯
• 英文名称: N-<(Benzyloxy)carbonyl>-2-phenyl-2,3-dihydro-4-pyridone
• 英文别名: benzyl 4-oxo-2-phenyl-3,4-dihydropyridine-1(2H)-carboxylate；2-phenyl-3,4-dihydro-4-pyridone；2-phenyl-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester；1-benzyloxycarbonyl-4-oxo-2-phenyl-3,4-dihydro-2H-pyridine；benzyl 4-oxo-2-phenyl-2,3-dihydropyridine-1-carboxylate
• CAS: 126378-73-2
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: HTXHSSNSXZBPKU-UHFFFAOYSA-N

物化性质

• 沸点：
  479.9±45.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氧代-2-苯基-3,4-二氢吡啶-1(2H)-羧酸苄酯 在 溶剂黄146 、 锌 作用下， 反应 2.0h， 以59.6%的产率得到benzyl 4-oxo-2-phenylpiperidine-1-carboxylate
  参考文献：
  名称：

  [EN] THERAPEUTIC COMPOUNDS AND METHODS OF USE THEREOF
  [FR] COMPOSÉS THÉRAPEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  这项发明提供了一个化合物的结构式：或其盐，其中变量RAA、n、环A、环B、R1a、R1b、R2、R3、R4、R5、R6、R7、R8和R9的含义如本文所述，并包含这种化合物的组合物以及使用这种化合物和组合物的方法。

  公开号：

  WO2017058821A1
• 作为产物：
  描述：

  氯甲酸苄酯 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 4-氧代-2-苯基-3,4-二氢吡啶-1(2H)-羧酸苄酯
  参考文献：
  名称：

  Conversion of N-acyl-2,3-dihydro-4-pyridones to 4-chloro-1,2-dihydropyridines using the Vilsmeier Reagent. Synthesis of (-)-coniine and (±)-lupinine

  摘要：

  The full details are given of a study on the conversion of dihydropyridones of the type 3 to 4-chloro-1,2-dihydropyridines 4 using a Vilsmeier reagent. The use of 1 equiv of Vilsmeier reagent under mild conditions (ClCHCCl2, rt) transformed several racemic N-acyl-2,3-dihydro-4-pyridones 3 to dihydropyridines 4 in very good to excellent yields (83-96%). A C-3 methyl group can be tolerated as was demonstrated in the preparation of 4-chloro-3-methyl-1,2-dihydropyridine 7 from dihydropyridone 6 in 90 % yield. The utility of this conversion was demonstrated in the synthesis of the piperidine alkaloid, (-)-coniine. The synthesis of (-)-coniine was completed in five steps from 4-methoxy-3-(triisopropylsilyl)pyridine in 54% overall yield. When 2,3-dihydro-4-pyridones are treated with excess Vilsmeier reagent, good yields of 4-chloro-3-formyl-1,2-dihydropyridines result. These heterocycles are useful intermediates for alkaloid preparation, as was shown by two syntheses of the quinolizidine alkaloid, (+/-)-lupinine, carried out in three and five steps, respectively.

  DOI：

  10.1021/jo00079a018

文献信息

• [EN] NOVEL PIPERIDINE COMPOUND<br/>[FR] NOUVEAU COMPOSE DE PIPERIDINE
  申请人：TANABE SEIYAKU CO

  公开号：WO2003099787A1

  公开（公告）日：2003-12-04

  The present invention provides a novel piperidine compound of the formula [I]: wherein Ring A represents an optionally substituted benzene ring, Ring B represents an optionally substituted benzene ring, R1 represents an optionally substituted alkyl group, an optionally substituted hydroxyl group, etc., or a group of the formula: (a) wherein R11 and R12 are the same or different, and each represents hydrogen atom, a substituted carbonyl group, a substituted sulfonyl group, an optionally substituted alkyl group, etc., R2 represents hydrogen atom, etc., Z represents oxygen atom or a group represented by -N(R3)-, R3 represents hydrogen atom or an alkyl group, etc., R4 represents hydrogen atom or an alkyl group, etc.,or a pharmaceutically acceptable salt thereof.

  本发明提供了一种新型哌啶化合物，其化学式为[I]：其中环A代表可选择取代的苯环，环B代表可选择取代的苯环，R1代表可选择取代的烷基团，可选择取代的羟基团等，或者化学式的一个基团：(a)其中R11和R12相同或不同，每个代表氢原子，取代的羰基团，取代的磺酰基团，可选择取代的烷基团等，R2代表氢原子等，Z代表氧原子或由-N(R3)-表示的基团，R3代表氢原子或烷基团等，R4代表氢原子或烷基团等，或其药学上可接受的盐。
• Pyrroles from TosMIC and substituted N-acyl-2,3-dihydro-4-pyridones: A short access to a 4-azaisoindole unit
  作者：Sezgin Kiren、Ayanna M. Brooks、Jada J. Graves

  DOI：10.1016/j.tetlet.2019.04.055

  日期：2019.5

  We investigated the reactions of substituted N-acyl-2,3-dihydro-4-pyridones with TosMIC reagent under various basic conditions to generate novel pyrrole products. These products were then transformed to substituted azaisoindoles in a couple of steps.

  我们研究了在各种碱性条件下，取代的N-酰基-2,3-二氢-4-吡啶酮与TosMIC试剂的反应，生成了新颖的吡咯产物。然后在两个步骤中将这些产物转化为取代的氮杂异吲哚。
• [EN] NK1 ANTAGONIST<br/>[FR] ANTAGONISTE DE NK1
  申请人：PFIZER PROD INC

  公开号：WO2004110996A1

  公开（公告）日：2004-12-23

  The invention is to a compound exhibiting neurokinin inhibitory properties, a pharmaceutical composition comprising same and a method of treatment for neurokinin-meditated conditions.Formula (I)

  这项发明涉及一种具有神经激肽抑制作用的化合物，包括该化合物的药物组合物以及用于神经激肽介导疾病的治疗方法。公式（I）
• Synthesis of C2-symmetric trans-2,6-diarylpiperidinones via aryl cuprate addition: an unexpected stereochemical outcome
  作者：Christopher L. Hamblett、David L. Sloman、Laura T. Kliman、Bruce Adams、Richard G. Ball、Matthew G. Stanton

  DOI：10.1016/j.tetlet.2007.01.135

  日期：2007.3

  An efficient procedure for the preparation of trans-2,6-diaryl piperidinones has been developed. Addition of aryl Grignard reagents to 2-aryl dihydropyridones under catalytic copper promoted conditions generates the trans isomer exclusively, an unprecedented stereochemical event. The X-ray structures of both starting material and product have been solved and shed light on the steric constraints and

  已经开发了制备反式-2,6-二芳基哌啶子酮的有效方法。在催化性铜促进条件下，将芳基格氏试剂与2-芳基二氢吡啶酮加成，将仅产生反式异构体，这是前所未有的立体化学事件。起始原料和产物的X射线结构均已解决，并阐明了空间限制和导致观察到产物的底物几何形状。反应条件容许各种芳族亲核试剂以良好的总产率产生C 2-对称产物。
• Thermodynamic equilibration of dihydropyridone enolates: application to the total synthesis of (+/−)-epiuleine
  作者：Edward S. Tasber、Robert M. Garbaccio

  DOI：10.1016/j.tetlet.2003.10.030

  日期：2003.12

  as its vinyl triflate (3). This enolate interconversion is dependent on the dihydropyridone C-2 substituent and can be interpreted in terms of conformational analysis. This novel scaffold (3) opens another avenue for the strategic deployment of dihydropyridones into both natural product synthesis and drug discovery. To this end, this method is highlighted by its use as a key step in a total synthesis

  在将2-取代的二氢吡啶酮（1）还原成1,4-之后，可以将所需的“动力学”烯醇酸酯在加热后进行异构化，以分离出热力学烯醇酸酯作为其三氟甲磺酸乙烯酯（3）。该烯醇化物相互转化取决于二氢吡啶酮C-2取代基，并且可以根据构象分析来解释。这种新颖的支架（3）为将二氢吡啶酮类策略性部署到天然产物合成和药物发现中开辟了另一条途径。为此，该方法通过将其用作（+/-）Epiuleine（14）的全合成中的关键步骤而得到强调。