(4R,5S)-5-(4-methoxyphenyl)-4-methyloxazolidin-2-one | 957777-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R,5S)-5-(4-methoxyphenyl)-4-methyloxazolidin-2-one
• 英文别名: (4R,5S)-5-(4-methoxyphenyl)-4-methyl-1,3-oxazolidin-2-one
• CAS: 957777-98-9
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: BLPUXPAZASULQR-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-5-(4-methoxyphenyl)-4-methyloxazolidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到(R)-(-)-2-(4-甲氧基苯基)-1-甲基乙胺
  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：

  (1S,2R)-2-[N-(t-butoxycarbonyl)amino]-1-(4-methoxyphenyl)propanol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以78%的产率得到(4R,5S)-5-(4-methoxyphenyl)-4-methyloxazolidin-2-one
  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.