(4S,6S)-6-(bromomethyl)-4-methyl-4-(1-methyl-1H-pyrazol-4-yl)-1,3-oxazinan-2-one | 1609247-62-2

• 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,6S)-6-(bromomethyl)-4-methyl-4-(1-methyl-1H-pyrazol-4-yl)-1,3-oxazinan-2-one
• CAS: 1609247-62-2
• 化学式: C₁₀H₁₄BrN₃O₂
• 分子量: 288.144
• InChiKey: QTERJIABSQSPRN-WPRPVWTQSA-N

物化性质

• 熔点：
  125-126 °C(Solvent: Ethyl acetate)
• 沸点：
  503.3±43.0 °C(predicted)
• 密度：
  1.62±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  56.15
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (S)-tert-butyl N-[1-methyl-1-(1-methyl-1H-pyrazol-4-yl)-3-butenyl]carbamate 在 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以50.943%的产率得到
  参考文献：
  名称：

  Diastereoselective In and Zn-mediated allylation of pyrazol-4-yl derived (R)-tert-butanesulfinyl imines: synthesis of enantiomerically pure 6-(pyrazol-4-yl)-piperidin-2,4-diones

  摘要：

  The In and Zn-mediated allylation of substituted pyrazol-4-yl derived (R)-N-tert-butanesulfinyl imines proceeds with high diastereoselectivity depending on the conditions and additives (up to 99.4% de). Thus, the synthesized diastereomeric homoallylsulfinamides were isolated and characterized as pure diastereomers, which were then converted into the corresponding pyrazol-4-yl-derived N-Boc-homoallylamines via consecutive treatment with HCl and Boc(2)O. The latter were then subjected to a sequence of reactions: cyclobromocarbamation with NBS and enolateisocyanate rearrangement with tBuOK to give novel enantiomerically pure (S)-6-(pyrazol-4-yl)-piperidine-2,4-diones in 88-96% yield. The absolute configurations of the allylation products were assigned by X-ray single crystal analysis of the intermediate bromomethylurethanes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.003