(3S,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one | 484021-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one
• 英文别名: (2S,5S)-2,5-dibenzyl-2,5-dihydro-1H-pyridin-6-one
• CAS: 484021-26-3
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: NOZLJCMIDLPRFN-QZTJIDSGSA-N

物化性质

• 沸点：
  478.0±34.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.5h， 生成 methyl (2R,5S,3Z)-2-benzyl-5-[(tert-butoxycarbonyl)amino]-6-phenylhex-3-enoate
  参考文献：
  名称：

  Unequivocal Synthesis of (Z)-Alkene and (E)-Fluoroalkene Dipeptide Isosteres To Probe Structural Requirements of the Peptide Transporter PEPT1

  摘要：

  Described is a novel synthetic route for dipeptide isosteres containing (Z)-alkene and (E)-fluoroalkene units as cis-amide bond equivalents via organocopper-mediated reduction of gamma-acetoxy- or gamma,gamma-difluoro-alpha,beta-unsaturated-delta-lactams. The synthesized isosteres were evaluated in terms of their affinities for the peptide transporter PEPT1. traps-Amide isosteres tended to possess higher affinities for PEPT1 as compared to the corresponding cis-amide bond equivalents.

  DOI：

  10.1021/ol052781k
• 作为产物：
  描述：

  (3S,6S)-3,6-dibenzyl-3,6-dihydro-1-(2,4-dimethoxy)benzylpyridin-2-one 在 三氟乙酸 作用下， 以99.9%的产率得到(3S,6S)-3,6-dibenzyl-3,6-dihydro-1H-pyridin-2-one
  参考文献：
  名称：

  Unequivocal Synthesis of (Z)-Alkene and (E)-Fluoroalkene Dipeptide Isosteres To Probe Structural Requirements of the Peptide Transporter PEPT1

  摘要：

  Described is a novel synthetic route for dipeptide isosteres containing (Z)-alkene and (E)-fluoroalkene units as cis-amide bond equivalents via organocopper-mediated reduction of gamma-acetoxy- or gamma,gamma-difluoro-alpha,beta-unsaturated-delta-lactams. The synthesized isosteres were evaluated in terms of their affinities for the peptide transporter PEPT1. traps-Amide isosteres tended to possess higher affinities for PEPT1 as compared to the corresponding cis-amide bond equivalents.

  DOI：

  10.1021/ol052781k

文献信息

• Ring Closing Metathesis of Unsaturated Amides as a Route to Short and Medium-Sized Unsaturated Lactams and to Ethylenic Pseudopeptides
  作者：Giang Vo-Thanh、Valérie Boucard、Hélène Sauriat-Dorizon、François Guibé

  DOI：10.1055/s-2001-9705

  日期：——

  Five- to eight-membered unsaturated lactams have been obtained through ring-closing metathesis of unsaturated amides of various chain lengths and substitution patterns. The obtention of nine-membered unsaturated lactams by the same procedure met only with limited success. Also described in this Letter is the obtention of the Z-ethylenic pseudopeptidic analog of l-Phe-l-Phe through hydrolytic ring opening of (3R,6S)-3,6-dibenzyl-3,6-dihydro-2-pyridone obtained by RCM.

  通过不同链长和取代模式的不饱和酰胺的环合复分解反应，获得了五至八元不饱和内酰胺。通过相同方法获得九元不饱和内酰胺仅取得了有限的成功。本信函还描述了通过RCM获得的（3R，6S）-3，6-二苄基-3，6-二氢-2-吡啶酮的水解开环反应，获得了l-Phe-l-Phe的Z-乙烯基类似物。
• Diastereospecific carbonylation of π-allylpalladium complexes to give 3,6-disubstituted 3,6-dihydro-1H-pyridin-2-ones
  作者：Julian G Knight、Kirill Tchabanenko

  DOI：10.1016/s0040-4020(02)00683-x

  日期：2002.8

  (Ph3P)(2)PdCl2 was found to be the most effective of a range of catalysts for decarboxylative carbonylation of (4S,5RS)-5-ethenyl-4-(2-propyl)oxazolidin-2-one to give the delta-lactam, (6S)-3,6-dihydro-6-(2-propyl)-1H-pyridin-2-one. In a similar way, diastereoisomerically pure (4S,5S)-4-benzyl-5-((Z)alk-1-enyl)oxazolidin-2-ones undergo stereospecific carbonylation to give (3R,6S)-6-benzyl-3-alkyl-3,6-dihydro-1H-pyridin-2-ones. The diastereoisomeric (4S,5R)-4-benzyl-5-((Z)alk-1-enyl)oxazolidin-2-ones give rise to a separable mixture of the corresponding (3S,6S)-6-benzyl-3-alkyl-3,6-dihydro-1H-pyridin-2-one and (4S,5S)-4-benzyl-5-((E)alk-1-enyl)oxazolidin-2-one. Under more forcing conditions, the latter oxazolidinone is carbonylated to the 3,6-anti-pyridinone. The stereochemical course of the reactions can be rationalized by formation of a pi-allyl palladium cation with inversion of configuration followed by carbonylation with retention. The stereospecificity observed in our system precludes metal-metal exchange of the pi-allyl complexes by a Pd(0) displacement process. (C) 2002 Elsevier Science Ltd. All rights reserved.