5-phenyl-1-(p-tolyl)pyrrolidin-2-one | 107182-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5-phenyl-1-(p-tolyl)pyrrolidin-2-one
• 英文别名: 1-(4-Methylphenyl)-5-phenylpyrrolin-2-one；1-(4-methylphenyl)-5-phenylpyrrolidin-2-one
• CAS: 107182-50-3
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: QCBVEXBXAKCLAV-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C
• 沸点：
  481.3±44.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙烯 在 六氟异丙醇 、 溴 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 8.5h， 生成 5-phenyl-1-(p-tolyl)pyrrolidin-2-one
  参考文献：
  名称：

  Hexafluoroisopropanol Promoted Ring‐Opening‐Cyclization of Donor–Acceptor Cyclopropanes with Primary Amines

  摘要：

  We reveal here a catalyst‐free, ring‐opening‐cyclization of donor‐acceptor cyclopropanes with primary amines to synthesize functionalized dihydropyrroles. This protocol avoids inert conditions and solvents promoted by hexafluoroisopropanol (HFIP). The reaction is quite general with aryl, alkyl, and alicyclic amines. A good number of cyclopropanes bearing keto groups reacted excellently to produce the desired products. Further, we complemented this method with Meldrum's acid‐derived cyclopropanes for synthesizing γ‐lactams. We have demonstrated the post‐synthetic applications of the products and gram‐scale synthesis to highlight the adaptability of this synthetic protocol.

  DOI：

  10.1002/ejoc.202400238

文献信息

• Reductive Amination/Cyclization of Keto Acids Using a Hydrosilane for Selective Production of Lactams versus Cyclic Amines by Switching of the Indium Catalyst
  作者：Yohei Ogiwara、Takuya Uchiyama、Norio Sakai

  DOI：10.1002/anie.201509465

  日期：2016.1.26

  amines by reductive amination, using an indium/silane combination. This relatively benign and safe catalyst/reductant system tolerates the use of a variety of functional groups, especially ones that are reduction‐sensitive. A direct switch from synthesizing lactams to synthesizing cyclic amines is achieved by changing the catalyst from In(OAc)3 to InI3. This conversion occurs by further reduction of the

  本文描述的是使用铟/硅烷组合通过还原胺化从酮酸与伯胺催化构筑N-取代的五元和六元内酰胺。这种相对温和，安全的催化剂/还原剂体系可以耐受各种官能团的使用，尤其是对还原敏感的官能团。通过将催化剂从In（OAc）3变为InI 3，可以实现从合成内酰胺到合成环胺的直接转换。该转化通过使用铟/硅烷对进一步还原内酰胺而发生。
• The Catalyst-Controlled Divergent Cascade Reactions of Homo-Propargylic Amines and Nitrones: Synthesis of Pyrrolo-Isoxazolidines and γ-Lactams
  作者：Yuanfang Kong、Yingze Liu、Boyi Wang、Shengli Li、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1002/adsc.201701476

  日期：2018.3.20

  Two controllable one‐pot cascade cyclization reactions of homopropargylic amines and nitrones were developed by using different metal Cu and Ag salts. The pyrroloisoxazolidines and γ‐lactams were obtained in good to high yields, respectively. Herein, nitrones played dual roles, both as 1,3‐dipoles and oxidants, and four stereocenters were simultaneously formed in the hydroamination cyclization‐1,3‐dipolar

  通过使用不同的金属铜和银盐，开发了两个可控制的一锅级均丙炔胺和硝酮的级联环化反应。吡咯并恶唑烷和γ-内酰胺分别以良好或高收率获得。在此，硝酮起着1,3-偶极子和氧化剂的双重作用，并且在存在AgOAc的情况下，在炔丙基胺和硝酮的加氢环化1,3-偶极环加成级联反应中同时形成了四个立体中心。
• Pernot; Willemart, Bulletin de la Societe Chimique de France, 1953, p. 324
  作者：Pernot、Willemart

  DOI：——

  日期：——
• KOVTUNENKO, V. A.;SOLOSHONOK, L. V.;TYLTIN, A. K.;TUROV, A. V.;BABICHEV, +, YKP. XIM. ZH., 1986, 52, N 1, 63-70
  作者：KOVTUNENKO, V. A.、SOLOSHONOK, L. V.、TYLTIN, A. K.、TUROV, A. V.、BABICHEV, +

  DOI：——

  日期：——