S-(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-4-(4-methoxyphenyl)-1-oxobutan-2-yl carbamothioate | 1023698-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: S-(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-4-(4-methoxyphenyl)-1-oxobutan-2-yl carbamothioate
• 英文别名: S-[(2R)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-(4-methoxyphenyl)-1-oxobutan-2-yl] carbamothioate
• CAS: 1023698-42-1
• 化学式: C₂₂H₂₄N₂O₅S
• 分子量: 428.509
• InChiKey: CFMUSFLRDKAMRQ-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S-(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-4-(4-methoxyphenyl)-1-oxobutan-2-yl carbamothioate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 、 (5R)-5-[2-(4-methoxyphenyl)ethyl]-1,3-thiazolidine-2,4-dione
  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
• 作为产物：
  描述：

  [(2R)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-(4-methoxyphenyl)-1-oxobutan-2-yl] thiocyanate 在 Pt(Me₂POH)3 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以92%的产率得到S-(R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-4-(4-methoxyphenyl)-1-oxobutan-2-yl carbamothioate
  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.