(NZ,R)-2-methyl-N-(2-oxo-1H-indol-3-ylidene)propane-2-sulfinamide | 1366339-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (NZ,R)-2-methyl-N-(2-oxo-1H-indol-3-ylidene)propane-2-sulfinamide
• CAS: 1366339-27-6
• 化学式: C₁₂H₁₄N₂O₂S
• 分子量: 250.321
• InChiKey: OXEZJQOUKRDQSM-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (NZ,R)-2-methyl-N-(2-oxo-1H-indol-3-ylidene)propane-2-sulfinamide 在 盐酸 、 potassium fluoride 、 magnesium bromide ethyl etherate 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 methyl (R)-3-amino-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  Lewis Acid Promoted Diastereoselective Addition of TMSCN and TMSCF₃ to Isatin-Derived N-Sulfinyl Ketimines: Synthesis of Optically Active Tetrasubstituted 3-Aminooxindoles

  摘要：

  A practical and efficient method for preparation of highly enantiomerically enriched 3-cyano-3-aminocaindoles and 3-trifluoromethyl-3-aminooxindoles with up to 99% optical purity by a Lewis acid promoted diastereoselective Strecker reaction and trifluoromethylation of isatin-derived N-tert-butanesulfinyl ketimines has been developed. This protocol allows direct use of N-free isatin substrates under mild conditions.

  DOI：

  10.1021/jo501360g
• 作为产物：
  描述：

  靛红 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 为溶剂， 生成 (NZ,R)-2-methyl-N-(2-oxo-1H-indol-3-ylidene)propane-2-sulfinamide
  参考文献：
  名称：

  Zinc-Mediated Diastereoselective Synthesis of 3-Amino Oxindoles by Addition of Methyl and Terminal Alkynes to N-tert-Butanesulfinyl Ketimines

  摘要：

  A zinc-mediated addition of methyl and terminal alkyines to chiral N-tert-butanesulfinyl ketimines for the preparation of optical quaternary 3-amino oxindoles was reported. In general, the operationally simple reaction affords the desired products in high yields and good to excellent diastereoselectivities. Subsequent convenient cleavage of sulfinyl protecting group under mild conditions was presented without racemization.

  DOI：

  10.1021/jo300110a

文献信息

• Highly diastereoselective entry into chiral spirooxindole-based 4-methyleneazetidines via formal [2+2] annulation reaction
  作者：G. Rainoldi、M. Faltracco、L. Lo Presti、A. Silvani、G. Lesma

  DOI：10.1039/c6cc05838h

  日期：——

  A diastereoselective, DABCO-catalyzed reaction of isatin-derived ketimines and allenoates is described. Exploiting the stereodirecting effect of the bulky tert-butanesulfinyl chiral auxiliary, the method provides an efficient access to single diastereoisomers...

  描述了一种非对映选择性的，DABCO催化的，源自靛红的酮亚胺和脲基甲酸酯的反应。利用笨重的叔丁烷亚磺酰基手性助剂的立体定向作用，该方法可有效地获得单一的非对映异构体。