(2S,3S)-N-[(S)-2-(6-methoxy-2-naphthyl)propionyl]-3-methyl-3-phenyl-2-aziridinemethanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3S)-N-[(S)-2-(6-methoxy-2-naphthyl)propionyl]-3-methyl-3-phenyl-2-aziridinemethanol
• 英文别名: (2S)-1-[(2S,3S)-3-(hydroxymethyl)-2-methyl-2-phenylaziridin-1-yl]-2-(6-methoxynaphthalen-2-yl)propan-1-one
• 化学式: C₂₄H₂₅NO₃
• 分子量: 375.467
• InChiKey: ZDTJNKREFWOPFK-IIICNMMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(2S)-3-苯基-2H-氮杂环丙烯-2-基]甲醇 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.5h， 生成 (2S,3S)-N-[(S)-2-(6-methoxy-2-naphthyl)propionyl]-3-methyl-3-phenyl-2-aziridinemethanol
  参考文献：
  名称：

  Lipase-Catalyzed Resolution of (2R*,3S*)- and (2R*,3R*)-3-Methyl-3-phenyl-2-aziridinemethanol at Low Temperatures and Determination of the Absolute Configurations of the Four Stereoisomers

  摘要：

  Lipase-catalyzed resolution of (2R*,3S*)-3-methyl-3-phenyl-2-aziridinemethanol, (+/-)-2, at low temperatures gave synthetically useful (2R,3S)-2 and its acetate (2S,3R)-2a with (2S)-selectivity (E = 55 at -40degreesC), while a similar reaction of (2R*,3R*)-3-methyl-3-phenyl-2-aziridinemethanol, (+/-)-3, gave (2S,3S)-3 and its acetate (2R,3R)-3a with (2R)-selectivity (E = 73 at -20degreesC). Compound (+/-)-2 was prepared conveniently via diastereoselective addition of MeMgBr to tert-butyl 3-phenyl2H-azirine-2-carboxylate, (+/-)-1a, which was successfully prepared by the Neber reaction of oxime tosylate of tert-butyl benzoyl acetate 7a. The tert-butyl ester was requisite to promote this reaction. For determination of the absolute configuration of (2S,3R)-2a, enantiopure (2S,3R)-2 was independently prepared in three steps involving diastereoselective methylation of 3-phenyl-2H-azirine-2-methanol, (S)-10, with MeMgBr. The absolute configuration of (2S,3S)-3 was determined by X-ray analysis of the corresponding N-(S)-2-(6-methoxy-2-naphthyl)propanoyl derivative (S,S,S)-13.

  DOI：

  10.1021/jo048243n

文献信息

• Lipase-Catalyzed Resolution of (2<i>R</i>*,3<i>S</i>*)- and (2<i>R</i>*,3<i>R</i>*)-3-Methyl-3-phenyl-2-aziridinemethanol at Low Temperatures and Determination of the Absolute Configurations of the Four Stereoisomers
  作者：Takashi Sakai、Yu Liu、Hiroshi Ohta、Toshinobu Korenaga、Tadashi Ema

  DOI：10.1021/jo048243n

  日期：2005.2.1

  Lipase-catalyzed resolution of (2R*,3S*)-3-methyl-3-phenyl-2-aziridinemethanol, (+/-)-2, at low temperatures gave synthetically useful (2R,3S)-2 and its acetate (2S,3R)-2a with (2S)-selectivity (E = 55 at -40degreesC), while a similar reaction of (2R*,3R*)-3-methyl-3-phenyl-2-aziridinemethanol, (+/-)-3, gave (2S,3S)-3 and its acetate (2R,3R)-3a with (2R)-selectivity (E = 73 at -20degreesC). Compound (+/-)-2 was prepared conveniently via diastereoselective addition of MeMgBr to tert-butyl 3-phenyl2H-azirine-2-carboxylate, (+/-)-1a, which was successfully prepared by the Neber reaction of oxime tosylate of tert-butyl benzoyl acetate 7a. The tert-butyl ester was requisite to promote this reaction. For determination of the absolute configuration of (2S,3R)-2a, enantiopure (2S,3R)-2 was independently prepared in three steps involving diastereoselective methylation of 3-phenyl-2H-azirine-2-methanol, (S)-10, with MeMgBr. The absolute configuration of (2S,3S)-3 was determined by X-ray analysis of the corresponding N-(S)-2-(6-methoxy-2-naphthyl)propanoyl derivative (S,S,S)-13.