(4R,5R)-(+)-5-(3-ethoxycarbonyl-2-oxo)propyl-3-(N-methyl)-4-benzyl-2-oxazolidinone | 199927-14-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (4R,5R)-(+)-5-(3-ethoxycarbonyl-2-oxo)propyl-3-(N-methyl)-4-benzyl-2-oxazolidinone
• 英文别名: ethyl 4-[(4R,5R)-4-benzyl-3-methyl-2-oxo-1,3-oxazolidin-5-yl]-3-oxobutanoate
• CAS: 199927-14-5
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: BDYBHXKEUYOUSJ-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R)-(+)-5-(3-ethoxycarbonyl-2-oxo)propyl-3-(N-methyl)-4-benzyl-2-oxazolidinone 生成 N-methyl-5-benzyl-2-pyrrolylacetate
  参考文献：
  名称：

  Synthesis, reaction, and structure of chiral N-methyl-2-oxazolidinones from 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates

  摘要：

  N-methyl-2-oxazolidinones (4) are obtained stereo-and regio-selectively when 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates (1) are treated with concentrated sulfuric acid (1.0 equiv.) supported on silicagel in dichloromethane at 0 degrees C. 4 were shown to be intermediates for the construction of N-methylpyrrole ring. The structure and properties of 4 and related compounds are also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10199-x
• 作为产物：
  描述：

  N-Boc-D-苯丙氨醛 在 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (4R,5R)-(+)-5-(3-ethoxycarbonyl-2-oxo)propyl-3-(N-methyl)-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  Synthesis, reaction, and structure of chiral N-methyl-2-oxazolidinones from 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates

  摘要：

  N-methyl-2-oxazolidinones (4) are obtained stereo-and regio-selectively when 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates (1) are treated with concentrated sulfuric acid (1.0 equiv.) supported on silicagel in dichloromethane at 0 degrees C. 4 were shown to be intermediates for the construction of N-methylpyrrole ring. The structure and properties of 4 and related compounds are also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10199-x

文献信息

• Kawano, Tomikazu; Negoro, Kenji; Nitta, Hajime, Heterocycles, 2000, vol. 52, # 3, p. 1261 - 1278
  作者：Kawano, Tomikazu、Negoro, Kenji、Nitta, Hajime、Ueda, Ikuo

  DOI：——

  日期：——
• Synthesis, reaction, and structure of chiral N-methyl-2-oxazolidinones from 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates
  作者：Tomikazu Kawano、Kenji Negoro、Ikuo Ueda

  DOI：10.1016/s0040-4039(97)10199-x

  日期：1997.11

  N-methyl-2-oxazolidinones (4) are obtained stereo-and regio-selectively when 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates (1) are treated with concentrated sulfuric acid (1.0 equiv.) supported on silicagel in dichloromethane at 0 degrees C. 4 were shown to be intermediates for the construction of N-methylpyrrole ring. The structure and properties of 4 and related compounds are also described. (C) 1997 Elsevier Science Ltd.