(4S)-3-(2-hydroxypropanoyl)-4-isopropyl-1,3-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-(2-hydroxypropanoyl)-4-isopropyl-1,3-oxazolidin-2-one
• 英文别名: (4S)-3-(2-hydroxypropanoyl)-4-propan-2-yl-1,3-oxazolidin-2-one
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: AVIGPXZUGSRPLG-COBSHVIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-4-异丙基-3-丙酰基-2-恶唑烷酮 在 三乙基硼 、 氧气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.75h， 生成 (4S)-3-(2-hydroxypropanoyl)-4-isopropyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives

  摘要：

  [GRAPHICS]Treatment of alpha-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding a-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the alpha-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently converted to alcohols, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.

  DOI：

  10.1021/ol990971n

文献信息

• Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives
  作者：Nobuhiro Kihara、Cyril Ollivier、Philippe Renaud

  DOI：10.1021/ol990971n

  日期：1999.11.1

  [GRAPHICS]Treatment of alpha-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding a-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the alpha-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently converted to alcohols, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.