N,1-dimethyl-2-oxo-N-phenylpyrrolidine-3-carboxamide | 1370018-06-6

• 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: N,1-dimethyl-2-oxo-N-phenylpyrrolidine-3-carboxamide
• CAS: 1370018-06-6
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: HBUUCPYUOAVVHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,1-dimethyl-2-oxo-N-phenylpyrrolidine-3-carboxamide 在 potassium tert-butylate 、 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以86%的产率得到1,1'-dimethylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione
  参考文献：
  名称：

  通过sp（2）CH和sp（3）CH键的“无过渡金属”分子内脱氢偶联（IDC）合成2-氧吲哚。

  摘要：

  经由“无过渡金属”的分子内脱氢偶联（IDC），已经完成了在假苄基位置带有全碳季中心的各种2-氧吲哚的合成。通过使用KOt-Bu催化β-N-芳基酰胺酯与烷基卤化物的一锅C-烷基化，然后脱氢偶联，通过形成碳-碳键来进行2-氧吲哚部分的构建。实验证据表明该反应朝向自由基介导的途径。

  DOI：

  10.3762/bjoc.12.111
• 作为产物：
  描述：

  benzyl 1-methyl-2-oxo-pyrrolidine-3-carboxylate 在 5%-palladium/activated carbon 、 2-氯-1-甲基吡啶碘化物 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 N,1-dimethyl-2-oxo-N-phenylpyrrolidine-3-carboxamide
  参考文献：
  名称：

  Copper-catalysed approach to spirocyclic oxindoles via a direct C–H, Ar-H functionalisation

  摘要：

  A practical and efficient entry to spirocyclic oxindoles from readily accessible anilide precursors, using only catalytic amounts of an inexpensive copper salt together with air as the sole re-oxidant, is described. In addition to providing access to a broad range of spiro-oxindole products, the utility of this method is demonstrated in a formal synthesis of the natural product, horsfiline. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.120

文献信息

• Intramolecular Dehydrogenative Coupling of sp² C–H and sp³ C–H Bonds: An Expeditious Route to 2-Oxindoles
  作者：Santanu Ghosh、Subhadip De、Badrinath N. Kakde、Subhajit Bhunia、Amit Adhikary、Alakesh Bisai

  DOI：10.1021/ol302767w

  日期：2012.12.7

  An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.
• DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids
  作者：Subhajit Bhunia、Santanu Ghosh、Dhananjay Dey、Alakesh Bisai

  DOI：10.1021/ol400899e

  日期：2013.5.17

  An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.
• Copper-catalysed approach to spirocyclic oxindoles via a direct C–H, Ar-H functionalisation
  作者：Catherine L. Moody、Vilius Franckevičius、Pauline Drouhin、Johannes E.M.N. Klein、Richard J.K. Taylor

  DOI：10.1016/j.tetlet.2012.01.120

  日期：2012.4

  A practical and efficient entry to spirocyclic oxindoles from readily accessible anilide precursors, using only catalytic amounts of an inexpensive copper salt together with air as the sole re-oxidant, is described. In addition to providing access to a broad range of spiro-oxindole products, the utility of this method is demonstrated in a formal synthesis of the natural product, horsfiline. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp² C–H and sp³ C–H bonds
  作者：Nivesh Kumar、Santanu Ghosh、Subhajit Bhunia、Alakesh Bisai

  DOI：10.3762/bjoc.12.111

  日期：——

  benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of beta-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for

  经由“无过渡金属”的分子内脱氢偶联（IDC），已经完成了在假苄基位置带有全碳季中心的各种2-氧吲哚的合成。通过使用KOt-Bu催化β-N-芳基酰胺酯与烷基卤化物的一锅C-烷基化，然后脱氢偶联，通过形成碳-碳键来进行2-氧吲哚部分的构建。实验证据表明该反应朝向自由基介导的途径。