<3(2R),4S>-3-(2-phenylseleno-1-oxopropyl)-4-(1-methylethyl)-2-oxazolidinone | 145588-99-4

• 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: <3(2R),4S>-3-(2-phenylseleno-1-oxopropyl)-4-(1-methylethyl)-2-oxazolidinone
• 英文别名: (4S)-3-[(2S)-2-phenylselanylpropanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 145588-99-4
• 化学式: C₁₅H₁₉NO₃Se
• 分子量: 340.281
• InChiKey: FCFBVCADIWBGLR-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <3(2R),4S>-3-(2-phenylseleno-1-oxopropyl)-4-(1-methylethyl)-2-oxazolidinone 在 sodium methylate 作用下， 反应 0.5h， 生成 (2R)-2-phenylselenopropanoic acid, methyl ester
  参考文献：
  名称：

  Synthesis of optically active α-phenylselenyl carbonyl derivatives

  摘要：

  Homochiral silyl enol ethers derived from N-acyl oxazolidinones can be phenyselenylated in high diastereoselectivity and good yield with phenylselenyl chloride. Removal of the chiral auxiliary is accompanied by some epimerisation. leading to isolation of the corresponding alpha-phenylselenyl methyl esters in moderate enantiomeric excess. A slightly improved enantiomeric excess is achieved if 4(S)-benzyl-2-oxazolidinethione 17 is used as a chiral auxiliary.

  DOI：

  10.1016/s0957-4166(00)82087-x
• 作为产物：
  描述：

  (S)-4-异丙基-3-丙酰基-2-恶唑烷酮 在 1,2-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone 、 lithium diisopropyl amide 作用下， 以 正戊烷 为溶剂， 反应 0.75h， 生成 <3(2R),4S>-3-(2-phenylseleno-1-oxopropyl)-4-(1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  Synthesis of optically active α-phenylselenyl carbonyl derivatives

  摘要：

  Homochiral silyl enol ethers derived from N-acyl oxazolidinones can be phenyselenylated in high diastereoselectivity and good yield with phenylselenyl chloride. Removal of the chiral auxiliary is accompanied by some epimerisation. leading to isolation of the corresponding alpha-phenylselenyl methyl esters in moderate enantiomeric excess. A slightly improved enantiomeric excess is achieved if 4(S)-benzyl-2-oxazolidinethione 17 is used as a chiral auxiliary.

  DOI：

  10.1016/s0957-4166(00)82087-x

文献信息

• Synthesis of optically active α-phenylselenyl carbonyl derivatives
  作者：Andrew B. Holmes、Alan Nadin、Peter J. O'Hanlon、Neil D. Pearson

  DOI：10.1016/s0957-4166(00)82087-x

  日期：1992.10

  Homochiral silyl enol ethers derived from N-acyl oxazolidinones can be phenyselenylated in high diastereoselectivity and good yield with phenylselenyl chloride. Removal of the chiral auxiliary is accompanied by some epimerisation. leading to isolation of the corresponding alpha-phenylselenyl methyl esters in moderate enantiomeric excess. A slightly improved enantiomeric excess is achieved if 4(S)-benzyl-2-oxazolidinethione 17 is used as a chiral auxiliary.