(RS)-(+/-)-2-(1-Methylethyl)-1-phenyl-2,3-dihydropyridin-4(1H)-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (RS)-(+/-)-2-(1-Methylethyl)-1-phenyl-2,3-dihydropyridin-4(1H)-one
• 英文别名: 2-isopropyl-1-phenyl-2,3-dihydropyridin-4(1H)-one；1-Phenyl-2-propan-2-yl-2,3-dihydropyridin-4-one
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: WLNYBQDFSHRIOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (RS)-(+/-)-N,N-Dimethyl-2-(1-methylethyl)-6-phenylimino-3,6-dihydro-2H-thiopyran-4-amine 在 sodium hydroxide 、 Raney nickel W₂ 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 (RS)-(+/-)-2-(1-Methylethyl)-1-phenyl-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  Conversion of 6-phenylimino-2H-thiopyran-4-amines to 1-phenyl-2,3-dihydro-4(1H)-pyridinones

  摘要：

  6-Phenylimino-3,6-dihydro-2H-thiopyran-4-amines (1) were converted to 1-phenyl-5,6-dihydropyridine-2(1H)-thiones (3). Those were akylated and hydrolyzed, thus yielding 6-melhylthio-1-phenyl-2,3-dihydro-4(1H)-pyridinones (5). Finally, the methylthio group was removed with Raney nickel giving the title compounds 6. The relative configurations of the formed diastereoisomeric dihydropyridinones have been investigated by NOE measurements.

  DOI：

  10.1007/bf00807066

文献信息

• Scandium(III)‐Zeolites as New Heterogeneous Catalysts for Imino‐Diels–Alder Reactions
  作者：Andrea Olmos、Benoit Louis、Patrick Pale

  DOI：10.1002/chem.201103624

  日期：2012.4.16

  demonstrates the first zeolite‐catalyzed synthesis of piperidine derivatives, including peptidomimetics and indoloquinolizidine alkaloids. The approach developed utilizes a highly effective one‐pot reaction cascade, through imine formation and imino‐Diels–Alder reactions, promoted by scandium‐loaded zeolites as a heterogeneous catalyst. The methodology described benefits from very low catalyst loadings (≤5 mol %

  这项研究证明了沸石催化的哌啶衍生物的首次合成，包括拟肽和吲哚并喹喔啉生物碱。所开发的方法通过形成亚胺和亚氨基Diels-Alder反应，通过scan载沸石作为非均相催化剂促进了高效的一锅反应级联反应。该方法从非常低的催化剂负载量（≤5摩尔％的Sc描述益处III），市售且容易获得的起始原料，和温和的反应条件。此外，Sc III沸石催化剂可轻松重复使用10次以上，而不会降低效率。
• Brønsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media
  作者：Takahiko Akiyama、Jun Takaya、Hirotaka Kagoshima

  DOI：10.1016/s0040-4039(99)01630-5

  日期：1999.10

  Three-component aza Diels-Alder reaction, starting from aldehyde, aniline, and Danishefsky's diene, took place smoothly under the influence of HBF4 in aqueous media to afford dihydro-4-pyridone derivatives in high yields.

  由醛，苯胺和Danishefsky的二烯开始的三组分氮杂Diels-Alder反应在HBF 4的影响下在水性介质中顺利进行，从而以高收率得到二氢-4-吡啶酮衍生物。
• Acid-Free Aza Diels−Alder Reaction of Danishefsky's Diene with Imines
  作者：Yu Yuan、Xin Li、Kuiling Ding

  DOI：10.1021/ol0265822

  日期：2002.9.1

  [reaction: see text] A highly efficient aza Diels-Alder reaction of Danishefsky's diene with imines was found to occur in methanol in the absence of any acids at room temperature to give corresponding 2-substituted dihydro-4-pyridone derivatives in high yields. This reaction can be also carried out in a three-component one-pot reaction manner. The reaction was found to proceed through a Mannich-type

  [反应：见正文]在室温下，在无酸的情况下，甲醇中发生Danishefsky's二烯与亚胺的高效氮杂Diels-Alder反应，以高收率得到相应的2-取代的二氢-4-吡啶酮衍生物。该反应也可以以三组分一锅法进行。发现该反应通过曼尼希型缩合机理进行。
• Synthesis of new analogues of diphenylpyraline
  作者：Robert Weis、Andreas J Kungl、Werner Seebacher

  DOI：10.1016/s0040-4020(03)00072-3

  日期：2003.2

  1-Unsubstituted 4-dimethylamino-5,6-dihydropyridine-2(1H)-thiones were converted to isomeric piperidin-4-ols which were separated and N-methylated to 2-substituted 1-methylpiperidin-4-ols. Their 1-phenyl analogues were prepared from 4-dimethylamino-5,6-dihydro-1-phenylpyridine-2(1H)-thiones. After their conversion to dihydro-1-phenylpyridin-4(1H)-ones the hydrogenation gave isomeric 1-phenylpiperidin-4-ols

  将1-未取代的4-二甲基氨基-5，6-二氢吡啶-2（1 H）-硫酮转化为异构体哌啶-4-醇，将其分离并N-甲基化为2-取代的1-甲基哌啶-4-醇。它们的1-苯基类似物由4-二甲基氨基-5,6-二氢-1-苯基吡啶-2（1 H）-硫酮制备。将它们转化为二氢-1-苯基吡啶-4（1 H）-后，氢化得到异构的1-苯基哌啶-4-醇，将其分离。通过各种方法对1-取代的哌啶-4-醇进行O-烷基化，得到二苯基吡啉的2-取代的类似物。检查了它们的抗分枝杆菌活性。通过NMR光谱研究哌啶衍生物的构型和构象。
• Wu, Liqiang; Yang, Limin; Yan, Fulin, Asian Journal of Chemistry, 2010, vol. 22, # 9, p. 6977 - 6982
  作者：Wu, Liqiang、Yang, Limin、Yan, Fulin

  DOI：——

  日期：——