C-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}-N-phenylnitrone | 1260501-43-6

• 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: C-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}-N-phenylnitrone
• CAS: 1260501-43-6
• 化学式: C₂₂H₁₈N₂O₃S
• 分子量: 390.463
• InChiKey: DMGOIUDCGGHIBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  65.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  C-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}-N-phenylnitrone 、 sodiodimethylmalonate 在 sodium methylate 作用下， 以 苯 为溶剂， 反应 4.5h， 以40%的产率得到dimethyl 3-hydroxy-5-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-y}-1-phenyl-2,5-dihydro-1H-pyrrole-2,4-dicarboxylate
  参考文献：
  名称：

  The stereoselective synthesis of highly functionalized tertiary 3-aminoindoles/anilines or dihydropyrroles from C-(3-indolyl)-N-aryl and C,N-diaryl nitrones

  摘要：

  We report on the novel properties of nitrones including their transformations via reactions with sodium malonates to give functionalized stereodefined derivatives of tertiary 3-aminoindoles or anilines, as well as fully-substituted dihydropyrroles. The outcome of the reactions is dependent mainly upon the nature of the starting C-nitrone substituent and solvent used. The formation of a new carbon nitrogen bond in the obtained amines occurs via a nucleophilic 1,2-aryl/3-indolyl shift from C to the adjacent nitrogen. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.045

文献信息

• Calcium catalyzed Mukaiyama–Mannich addition of silyl enol ethers to nitrones
  作者：Elizabeth A. Congdon、Kristine A. Nolin

  DOI：10.1016/j.catcom.2016.02.003

  日期：2016.4

  A method for synthesizing β-(silyloxy)amino carbonyls through the addition of ketone-derived silyl enol ethers to N-phenyl nitrones has been developed. The transformation is catalyzed by a commercially available calcium(II) complex affording β-(silyloxy)amino carbonyls in good to excellent yield.

  已经开发了通过将酮衍生的甲硅烷基烯醇醚加到N-苯基硝酮中来合成β-（甲硅烷氧基）氨基羰基的方法。所述转化通过可商购获得的钙（II）配合物催化，所述钙（II）配合物以良好至优异的产率提供β-（甲硅烷氧基）氨基羰基。
• Synthesis of 1,2-Oxazinanes via Hydrogen Bond Mediated [3 + 3] Cycloaddition Reactions of Oxyallyl Cations with Nitrones
  作者：Lingbowei Hu、Michael Rombola、Viresh H. Rawal

  DOI：10.1021/acs.orglett.8b02301

  日期：2018.9.7

  the development of [3 + 3] cycloaddition reactions between oxyallyl cations and nitrones to yield 1,2-oxazinane heterocycles. Oxyallyl cation intermediates, generated in situ from α-tosyloxy ketones in the presence of hexafluoro-2-propanol (HFIP), a cosolvent, and a base, are found to react with a range of nitrones to afford 1,2-oxazinanes in good to high yields. The reactions are catalyzed by hydrogen-bond

  本文报道了在氧烯丙基阳离子和硝酮之间[3 + 3]环加成反应的发展，以产生1,2-恶嗪烷杂环。发现在六氟-2-丙醇（HFIP），助溶剂和碱的存在下，由α-甲苯磺酰氧基酮原位生成的草酸烯丙基阳离子中间体可与多种硝酮反应，从而提供良好的1,2-恶嗪二酮高产。该反应由氢键供体（例如苯酚和方酸酰胺）催化，观察到4-硝基苯酚的非对映选择性大大提高。