(3R,2'R,1''R)-2,2-dimethyl-3-(4-methoxyphenylamino)-3-[1'-(1''-phenylethyl)aziridin-2'-yl]propionic acid methyl ester | 854763-30-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,2'R,1''R)-2,2-dimethyl-3-(4-methoxyphenylamino)-3-[1'-(1''-phenylethyl)aziridin-2'-yl]propionic acid methyl ester
• 英文别名: methyl (3R)-3-(4-methoxyanilino)-2,2-dimethyl-3-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]propanoate
• CAS: 854763-30-7
• 化学式: C₂₃H₃₀N₂O₃
• 分子量: 382.503
• InChiKey: IOKLLLUVVMBKFW-CKKISIDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  50.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,2'R,1''R)-2,2-dimethyl-3-(4-methoxyphenylamino)-3-[1'-(1''-phenylethyl)aziridin-2'-yl]propionic acid methyl ester 、 六氯丙酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以67%的产率得到(4'S,5'R,1''R)-2-[4'-chloromethyl-1'-(4-methoxyphenyl)-2-oxo-3-(1''-phenylethyl)imidazolidin-5'-yl]-2,2-dimethylpropionic acid methyl ester
  参考文献：
  名称：

  Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles

  摘要：

  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.

  DOI：

  10.1016/j.tet.2005.07.064
• 作为产物：
  描述：

  1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 、 (2'R,1''R)-(4-methoxyphenyl){[1-(1''-phenylethyl)aziridin-2'-yl]methylene}amine 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(3R,2'R,1''R)-2,2-dimethyl-3-(4-methoxyphenylamino)-3-[1'-(1''-phenylethyl)aziridin-2'-yl]propionic acid methyl ester
  参考文献：
  名称：

  Addition reactions to chiral aziridine-2-carboxaldimine toward various enantiopure nitrogen-containing heterocycles

  摘要：

  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.

  DOI：

  10.1016/j.tet.2005.07.064

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.