(4S)-N-<(2S)-2-methyl-3-(2-methoxyphenylthio)propanoyl>-4-phenyloxazolidin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S)-N-<(2S)-2-methyl-3-(2-methoxyphenylthio)propanoyl>-4-phenyloxazolidin-2-one
• 化学式: C₂₀H₂₁NO₄S
• 分子量: 371.457
• InChiKey: UHBTYRPBJWAEKG-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-甲氧基苯硫酚 、 (4S)-3-(2-methyl-2-propenoyl)-4-phenyl-2-oxazolidinone 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (4S)-N-<(2S)-2-methyl-3-(2-methoxyphenylthio)propanoyl>-4-phenyloxazolidin-2-one 、 (4S)-N-<(2R)-2-methyl-3-(2-methoxyphenylthio)propanoyl>-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Asymmetric conjugate addition of thiols to chiral methacryloyloxazolidinones

  摘要：

  The conjugate addition of thioacetic acid (3 equivalents) to (4S)-4-phenyl-N-methacryloyloxazolidin-2-one (3) in the presence of TiCl4 (1.5 equivalents) gave the addition adducts in 87% yield and only 14% de. When this reaction was carried out in the absence of TiCl4, good diastereoselectivity (94% de) was observed. A similar result was obtained by employing thiobenzoic acid as a nucleophile. The reaction of 3 with other thiols, such as thiophenol, 4-methoxythiophenol, 2-methoxytbiophenol, methyl 3-mercatopropionate, methyl thioglycolate and methyl thiosalicylate, required TiCl4 (1.5 equivalents) to give the addition adducts in good chemical yields and the diastereoselectivities are ranging from 50 to 82% de. 2-Aminothiophenol was also employed in this study to give the addition adducts in 60% yield and 70% de when the reaction was carried out in the absence of TiCl4. In the presence of TiCl4, this reaction provided the addition adducts as racemic mixture in 28% yield along with 1,5-benzothiazepin-4-one 10 in 56% yield.

  DOI：

  10.1016/0957-4166(95)00208-7

文献信息

• Asymmetric conjugate addition of thiols to chiral methacryloyloxazolidinones
  作者：Tsung-Chin Tseng、Ming-Jing Wu

  DOI：10.1016/0957-4166(95)00208-7

  日期：1995.7

  The conjugate addition of thioacetic acid (3 equivalents) to (4S)-4-phenyl-N-methacryloyloxazolidin-2-one (3) in the presence of TiCl4 (1.5 equivalents) gave the addition adducts in 87% yield and only 14% de. When this reaction was carried out in the absence of TiCl4, good diastereoselectivity (94% de) was observed. A similar result was obtained by employing thiobenzoic acid as a nucleophile. The reaction of 3 with other thiols, such as thiophenol, 4-methoxythiophenol, 2-methoxytbiophenol, methyl 3-mercatopropionate, methyl thioglycolate and methyl thiosalicylate, required TiCl4 (1.5 equivalents) to give the addition adducts in good chemical yields and the diastereoselectivities are ranging from 50 to 82% de. 2-Aminothiophenol was also employed in this study to give the addition adducts in 60% yield and 70% de when the reaction was carried out in the absence of TiCl4. In the presence of TiCl4, this reaction provided the addition adducts as racemic mixture in 28% yield along with 1,5-benzothiazepin-4-one 10 in 56% yield.