(4R)-4-benzyl-3-[4-(4-methoxyphenyl)butanoyl]-1,3-oxazolidin-2-one | 1023698-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R)-4-benzyl-3-[4-(4-methoxyphenyl)butanoyl]-1,3-oxazolidin-2-one
• CAS: 1023698-36-3
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: WBEVBOHTZZWYLU-GOSISDBHSA-N

物化性质

• 熔点：
  70.8-71.6 °C
• 沸点：
  542.8±33.0 °C(predicted)
• 密度：
  1.199±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[4-(4-methoxyphenyl)butanoyl]-1,3-oxazolidin-2-one 、 N-thiocyanatosuccinimide 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以83%的产率得到[(2R)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-(4-methoxyphenyl)-1-oxobutan-2-yl] thiocyanate
  参考文献：
  名称：

  Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones

  摘要：

  Electrophilic alpha-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. alpha-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.034

文献信息

• Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones
  作者：J.R. Falck、Shuanhu Gao、Ravi Naga Prasad、Sreenivasulu Reddy Koduru

  DOI：10.1016/j.bmcl.2008.02.034

  日期：2008.3

  Electrophilic alpha-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. alpha-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization. (C) 2008 Elsevier Ltd. All rights reserved.