(2R,1'R)-2-(1'-phenylethyl)aziridinyl 4-methoxyphenyl ketone | 910655-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,1'R)-2-(1'-phenylethyl)aziridinyl 4-methoxyphenyl ketone
• 英文别名: (4-methoxyphenyl)-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]methanone
• CAS: 910655-40-2
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: KRPMSWXXAAOUOG-BZSPAODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,1'R)-2-(1'-phenylethyl)aziridinyl 4-methoxyphenyl ketone 在 sodium tetrahydroborate 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以13.2 g的产率得到(2R,1'S,1''R)-[(1''-phenylethyl)aziridin-2-yl]-[1'-(4-methoxyphenyl)]methanol
  参考文献：
  名称：

  Assymetric formal synthesis of (−)-formoterol and (−)-tamsulosin

  摘要：

  Biologically important (2R)-2-amino-3-phenylpropanes consisted in commercial drugs including (R,R)-formoterol, and (R)-tamsulosin were prepared from chiral (2R)-aziridine-2-carboxylate without any chromatographic separation. Key reactions include regio- and stereoselective ring opening reaction of aziridin-2-yl-phenylmethanol and subsequent cyclization toward enantiopure 4,5-disubastitued oxazolidin-2-ones as synthetic intermediates.

  DOI：

  10.1016/s0385-5414(07)81100-2
• 作为产物：
  描述：

  1-{(2R)-1-[(1R)-1-phenylethyl]-aziridine}-2-carboxylic acid methoxy methyl amide 、 4-甲氧基苯基溴化镁 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (2R,1'R)-2-(1'-phenylethyl)aziridinyl 4-methoxyphenyl ketone
  参考文献：
  名称：

  Assymetric formal synthesis of (−)-formoterol and (−)-tamsulosin

  摘要：

  Biologically important (2R)-2-amino-3-phenylpropanes consisted in commercial drugs including (R,R)-formoterol, and (R)-tamsulosin were prepared from chiral (2R)-aziridine-2-carboxylate without any chromatographic separation. Key reactions include regio- and stereoselective ring opening reaction of aziridin-2-yl-phenylmethanol and subsequent cyclization toward enantiopure 4,5-disubastitued oxazolidin-2-ones as synthetic intermediates.

  DOI：

  10.1016/s0385-5414(07)81100-2

文献信息

• Ring opening of 2-acylaziridines by acid chlorides
  作者：Yongeun Kim、Hyun-Joon Ha、Hoseop Yun、Baeck Kyoung Lee、Won Koo Lee

  DOI：10.1016/j.tet.2006.06.025

  日期：2006.9

  Good nucleophilicity of the ring nitrogen in chiral (2R,1'R)-2-acyl-(1'-phenylethyl)aziridines initiated the reaction with various acid chlorides to form the corresponding acylaziridinium ion intermediates whose rings were opened by the chloride anion to yield the beta-amino-alpha-chlorocarbonyl compounds. The subsequent displacement of the chloride with the internal oxygen nucleophile originated from methylchloroformate, acetyl chloride, and methyl chlorooxoacetate yielded oxazolidin-2-ones, beta-amino-alpha-acetyloxypropionates, and morpholin-2,3-diones, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• Assymetric formal synthesis of (−)-formoterol and (−)-tamsulosin
  作者：Y KIM、L KANG、H HA、S KO、W LEE

  DOI：10.1016/s0385-5414(07)81100-2

  日期：2007.10.1

  Biologically important (2R)-2-amino-3-phenylpropanes consisted in commercial drugs including (R,R)-formoterol, and (R)-tamsulosin were prepared from chiral (2R)-aziridine-2-carboxylate without any chromatographic separation. Key reactions include regio- and stereoselective ring opening reaction of aziridin-2-yl-phenylmethanol and subsequent cyclization toward enantiopure 4,5-disubastitued oxazolidin-2-ones as synthetic intermediates.