(2R,1'S,1''R)-[(1''-phenylethyl)aziridin-2-yl]-[1'-(4-methoxyphenyl)]methanol | 957777-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,1'S,1''R)-[(1''-phenylethyl)aziridin-2-yl]-[1'-(4-methoxyphenyl)]methanol
• 英文别名: (S)-(4-methoxyphenyl)-[(2R)-1-[(1R)-1-phenylethyl]aziridin-2-yl]methanol
• CAS: 957777-96-7
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: IEQYHKAGAVBFQC-UQIORVJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,1'S,1''R)-[(1''-phenylethyl)aziridin-2-yl]-[1'-(4-methoxyphenyl)]methanol 、 二碳酸二叔丁酯 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 以89%的产率得到(1S,2R)-2-[N-(t-butoxycarbonyl)amino]-1-(4-methoxyphenyl)propanol
  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：

  (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

文献信息

• 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.