(1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]ethyl}amine | 694526-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]ethyl}amine
• 英文别名: 4-methoxy-N-[(1R)-1-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]ethyl]aniline
• CAS: 694526-66-4
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: YVYLINHUMJJUDS-XUTCFEKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  24.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]ethyl}amine 在 palladium on activated charcoal 氢气 作用下， 以82%的产率得到2-(p-methoxyphenyl)aminobutane
  参考文献：
  名称：

  Highly Stereoselective Addition of Organomagnesium Reagents to Aziridinyl-2-carboxaldimine: Preparation of Enantiopure 2-Aminomethylaziridines and 4,5-Disubstituted Imidazolidin-2-ones

  摘要：

  以高度立体选择性的方式将烷基和芳基镁试剂添加到手性[1′(R)-α-甲基苄基]氮丙啶-2(R)-甲醛亚胺中，得到2-氨基甲基氮丙啶。用三光气和NaH进一步处理2-氨基甲基氮丙啶，得到对映体纯的5-烷基-或5-芳基-4-氯甲基咪唑啉-2-酮。

  DOI：

  10.1055/s-2004-815444
• 作为产物：
  描述：

  (R)-1-((R)-1-phenylethyl)aziridine-2-carbaldehyde 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 (1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]ethyl}amine
  参考文献：
  名称：

  Highly Stereoselective Addition of Organomagnesium Reagents to Aziridinyl-2-carboxaldimine: Preparation of Enantiopure 2-Aminomethylaziridines and 4,5-Disubstituted Imidazolidin-2-ones

  摘要：

  以高度立体选择性的方式将烷基和芳基镁试剂添加到手性[1′(R)-α-甲基苄基]氮丙啶-2(R)-甲醛亚胺中，得到2-氨基甲基氮丙啶。用三光气和NaH进一步处理2-氨基甲基氮丙啶，得到对映体纯的5-烷基-或5-芳基-4-氯甲基咪唑啉-2-酮。

  DOI：

  10.1055/s-2004-815444

文献信息

• Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles
  作者：Heui-Yoon Noh、Sang-Woo Kim、Seong In Paek、Hyun-Joon Ha、Hoseop Yun、Won Koo Lee

  DOI：10.1016/j.tet.2005.07.064

  日期：2005.9

  Chiral (2R,1'R)-(1'-phenylethyl)aziridine-2-carboxaldimine was utilized as a nitrogen-containing starting substrate for the preparation of various enantiopure nitrogen-containing heterocycles. The additions of nucleophiles including organomagnesium reagents, cyanotrimethyl si lane and ketene acetal to the chiral (2R,1'R)-(1'-phenylethyl)aziridine-2-carboxaldimine proceeded in highly stereoselective manner via chelation controlled transition states. Subsequent treatment of adducts with triphosgene and NaH yielded 5-substituted-4-chloromethylimidazolidin-2-ones. This imine was also served as either aza-diene or aza-dienophile with olefin or diene to provide hetero-Diels-Alder adducts 2-aziridinylpiperidines or 1,2,3,4-tetrahydroquinolines. (c) 2005 Elsevier Ltd. All rights reserved.
• Highly Stereoselective Addition of Organomagnesium Reagents to Aziridinyl-2-carboxaldimine: Preparation of Enantiopure 2-Aminomethylaziridines and 4,5-Disubstituted Imidazolidin-2-ones
  作者：Hyun-Joon Ha、Won Koo Lee、Man-Jin Suh、Sang Woo Kim、Seong In Beak

  DOI：10.1055/s-2004-815444

  日期：——

  The addition of alkyl- and arylmagnesium reagents to chiral [1′(R)-α-methylbenzyl]aziridine-2(R)-carboxaldimines was carried out in a highly stereoselective manner to give 2-aminomethylaziridine. Further treatment of 2-aminomethylaziridines with triphosgene and NaH afforded enantiopure 5-alkyl- or 5-aryl-4-chloromethylimidazolidin-2-ones.

  以高度立体选择性的方式将烷基和芳基镁试剂添加到手性[1′(R)-α-甲基苄基]氮丙啶-2(R)-甲醛亚胺中，得到2-氨基甲基氮丙啶。用三光气和NaH进一步处理2-氨基甲基氮丙啶，得到对映体纯的5-烷基-或5-芳基-4-氯甲基咪唑啉-2-酮。