(S)-5-((4-morpholino-1,2,5-thiadiazol-3-yloxy)-methyl)-3-tert-butyloxazolidin-2-one | 56526-15-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-5-((4-morpholino-1,2,5-thiadiazol-3-yloxy)-methyl)-3-tert-butyloxazolidin-2-one
• 英文别名: (5S)-3-tert-butyl-5-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxymethyl]-1,3-oxazolidin-2-one
• CAS: 56526-15-9
• 化学式: C₁₄H₂₂N₄O₄S
• 分子量: 342.419
• InChiKey: RODJYIZCCGCNFA-JTQLQIEISA-N

物化性质

• 沸点：
  550.4±50.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-5-((4-morpholino-1,2,5-thiadiazol-3-yloxy)-methyl)-3-tert-butyloxazolidin-2-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.0h， 生成 马来酸噻吗洛尔
  参考文献：
  名称：

  Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines

  摘要：

  An efficient enantioselective synthesis of (S)-timolol has been described using chiral Co-salen-catalyzed kinetic resolution of less expensive (+/-)-epichlorohydrin with 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole in good overall yield (55%) and excellent enantioselectivity (98%). Synthesis of (S)-timolol has also been achieved using hydrolytic kinetic resolution as well as asymmetric dihydroxylation routes in 90% ee and 56% ee, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.057
• 作为产物：
  描述：

  3-氯-4-吗啉基-1,2,5-噻二唑 、 5-(羟基甲基)-3-(2-甲基-2-丙基)-1,3-恶唑烷-2-酮 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 12.0h， 以75%的产率得到(S)-5-((4-morpholino-1,2,5-thiadiazol-3-yloxy)-methyl)-3-tert-butyloxazolidin-2-one
  参考文献：
  名称：

  Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines

  摘要：

  An efficient enantioselective synthesis of (S)-timolol has been described using chiral Co-salen-catalyzed kinetic resolution of less expensive (+/-)-epichlorohydrin with 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole in good overall yield (55%) and excellent enantioselectivity (98%). Synthesis of (S)-timolol has also been achieved using hydrolytic kinetic resolution as well as asymmetric dihydroxylation routes in 90% ee and 56% ee, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.057