trans-(2S,3S)-1-methansulfonyl-2-methyl-3-phenylaziridin

• 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: trans-(2S,3S)-1-methansulfonyl-2-methyl-3-phenylaziridin
• 英文别名: (2S,3S)-2-methyl-1-(methanesulfonyl)-3-phenylaziridine；(2S,3S)-2-methyl-1-methylsulfonyl-3-phenylaziridine
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: PXSWABCEYSHOKL-OZRKRLJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二苯基膦 、 trans-(2S,3S)-1-methansulfonyl-2-methyl-3-phenylaziridin 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到[(1R,2S)-2-methansulfonamido-1-phenylpropyl]diphenylphosphan
  参考文献：
  名称：

  Funktionelle Phosphane

  摘要：

  The preparation of optically active beta -aminophosphane ligands, (-)-(1R,2S)-Ph2PCH(Ph)CH(Me)NH2 (5), (+)-(1S,2S)Ph2PCH(Ph)CH(Me)NH2 (6), (-)-(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe (7), and (1R,2S)-Ph2PCH(Ph)CH(Me)NHSO2Me (8), as well as of related beta -aminophosphinites, (+)-(1R,2S)-Ph2POCH(Ph)CH(Me)NH2 (9), (-)-(1R,2R)-Ph2POCH(Ph)CH(Me)NHMe (10), (+)-(1S,2S)-Ph2POCH(Ph)CH(Me)NHMe (11), and (-)-(1R,2S)-Ph2POCH(Ph)CH(Me)NHMe (12), from commercially available ephedrine, norephedrine, and pseudoephedrine enantiomers is reported. Ligands 6 and 7 react with [M(eta (4)-1,5-C8H12)(2)]BF4 (M = Rh, Ir) to afford the P,N chelate complexes [{(1S,2S)-Ph2PCH(Ph)CH(Me)NH2-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (13), [{(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (14), and [{(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (15), Of which 14 and 15 exist as mixtures of three sterically locked ring conformers. The molecular structures of the prevailing lambda (R-C,R-C,S-N) form of rhodium complex 14, of beta -aminophosphane 8 and of the hydrochloride of ligand 7 were determined by single-crystal X-ray diffraction. In the presence of added triethylamine, iridium complex 15 catalyzes the enantioselective hydrogenation of acetophenone, giving (-)-(S)-1-phenylethanol in modest enantiomeric excess (40%). (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00520-9
• 作为产物：
  描述：

  [(1R,2S)-2-(methanesulfonamido)-1-phenylpropyl] methanesulfonate 在 肼 作用下， 以 四氢呋喃 为溶剂， 生成 trans-(2S,3S)-1-methansulfonyl-2-methyl-3-phenylaziridin
  参考文献：
  名称：

  A facile, one-pot synthesis of Ephedra-based aziridines

  摘要：

  A series of enantiomerically and diastereomerically enriched N-sulfonylaziridines have been prepared by a single-pot process from (1R,2S)- and (1S,2R)-norephedrine and (1S,2S)-pseudonorephedrine. The cyclization process involved N-sulfonylation of the Ephedra alkaloid followed by O-sulfonylation with methanesulfonyl chloride. The bis(sulfonyl) Ephedra derivatives were treated with either hydrazine or sodium hydroxide to afford the N-sulfonylaziridines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.016

文献信息

• Funktionelle Phosphane
  作者：Lutz Dahlenburg、Rainer Götz

  DOI：10.1016/s0022-328x(00)00520-9

  日期：2001.1

  The preparation of optically active beta -aminophosphane ligands, (-)-(1R,2S)-Ph2PCH(Ph)CH(Me)NH2 (5), (+)-(1S,2S)Ph2PCH(Ph)CH(Me)NH2 (6), (-)-(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe (7), and (1R,2S)-Ph2PCH(Ph)CH(Me)NHSO2Me (8), as well as of related beta -aminophosphinites, (+)-(1R,2S)-Ph2POCH(Ph)CH(Me)NH2 (9), (-)-(1R,2R)-Ph2POCH(Ph)CH(Me)NHMe (10), (+)-(1S,2S)-Ph2POCH(Ph)CH(Me)NHMe (11), and (-)-(1R,2S)-Ph2POCH(Ph)CH(Me)NHMe (12), from commercially available ephedrine, norephedrine, and pseudoephedrine enantiomers is reported. Ligands 6 and 7 react with [M(eta (4)-1,5-C8H12)(2)]BF4 (M = Rh, Ir) to afford the P,N chelate complexes [(1S,2S)-Ph2PCH(Ph)CH(Me)NH2-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (13), [(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (14), and [(1R,2R)-Ph2PCH(Ph)CH(Me)NHMe-kappaN,kappaP}Ir(eta (4)-1,5-C8H12)]BF4 (15), Of which 14 and 15 exist as mixtures of three sterically locked ring conformers. The molecular structures of the prevailing lambda (R-C,R-C,S-N) form of rhodium complex 14, of beta -aminophosphane 8 and of the hydrochloride of ligand 7 were determined by single-crystal X-ray diffraction. In the presence of added triethylamine, iridium complex 15 catalyzes the enantioselective hydrogenation of acetophenone, giving (-)-(S)-1-phenylethanol in modest enantiomeric excess (40%). (C) 2001 Elsevier Science B.V. All rights reserved.
• A facile, one-pot synthesis of Ephedra-based aziridines
  作者：Jonathan A. Groeper、Joel B. Eagles、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2009.07.016

  日期：2009.9

  A series of enantiomerically and diastereomerically enriched N-sulfonylaziridines have been prepared by a single-pot process from (1R,2S)- and (1S,2R)-norephedrine and (1S,2S)-pseudonorephedrine. The cyclization process involved N-sulfonylation of the Ephedra alkaloid followed by O-sulfonylation with methanesulfonyl chloride. The bis(sulfonyl) Ephedra derivatives were treated with either hydrazine or sodium hydroxide to afford the N-sulfonylaziridines. (C) 2009 Elsevier Ltd. All rights reserved.