(4S,2'S,3'R)-3-(3'-phenyloxiranecarbonyl)-4-(1-methylethyl)-2-oxazolidinone | 1256455-47-6

• 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,2'S,3'R)-3-(3'-phenyloxiranecarbonyl)-4-(1-methylethyl)-2-oxazolidinone
• 英文别名: (4S)-3-[(2S,3R)-3-phenyloxirane-2-carbonyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1256455-47-6
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: YBMWXPZPFNCPMV-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4S)-4-isopropyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 在 Oxone 、 三氯丙酮 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 10.0h， 生成 (4S,2'S,3'R)-3-(3'-phenyloxiranecarbonyl)-4-(1-methylethyl)-2-oxazolidinone 、 (4S,2'R,3'S)-3-(3'-phenyloxiranecarbonyl)-4-(1-methylethyl)-2-oxazolidinone
  参考文献：
  名称：

  Asymmetric epoxidation of cinnamic acid derivatives by in situ generated dioxiranes of chloroacetones: scope and limitations

  摘要：

  Efficient epoxidation of chiral cinnamic acid derivatives has been achieved by in situ generated dioxiranes of chloroacetones with moderate to good diastereoselectivity (dr up to 90:10) in high yields. Reactivity of cinnamic acid derivatives containing different chiral auxiliaries versus chloroacetones-monochloroacetone 3 (MCA), 1,1-dichloroacetone 4 (DCA) and 1,1,1-trichloroacetone 5 (TCA) and Oxone (TM) loading was studied. Both Oxone (TM) loading and reaction time reduce with an increase of chlorine atoms in the acetone. The use of 1.1 equiv of TCA was found to be effective for the epoxidation of cinnamate substrates and enhances the reaction up to 4-10-fold compared to acetone and that also decreases the Oxone (TM) loading. This method provided methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (-)-2, a key intermediate for the synthesis of diltiazem hydrochloride, with >99% of enantiomeric purity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.012

文献信息

• Asymmetric epoxidation of cinnamic acid derivatives by in situ generated dioxiranes of chloroacetones: scope and limitations
  作者：Saumen Hajra、Manishabrata Bhowmick

  DOI：10.1016/j.tetasy.2010.07.012

  日期：2010.9

  Efficient epoxidation of chiral cinnamic acid derivatives has been achieved by in situ generated dioxiranes of chloroacetones with moderate to good diastereoselectivity (dr up to 90:10) in high yields. Reactivity of cinnamic acid derivatives containing different chiral auxiliaries versus chloroacetones-monochloroacetone 3 (MCA), 1,1-dichloroacetone 4 (DCA) and 1,1,1-trichloroacetone 5 (TCA) and Oxone (TM) loading was studied. Both Oxone (TM) loading and reaction time reduce with an increase of chlorine atoms in the acetone. The use of 1.1 equiv of TCA was found to be effective for the epoxidation of cinnamate substrates and enhances the reaction up to 4-10-fold compared to acetone and that also decreases the Oxone (TM) loading. This method provided methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (-)-2, a key intermediate for the synthesis of diltiazem hydrochloride, with >99% of enantiomeric purity. (C) 2010 Elsevier Ltd. All rights reserved.