(3aS,4S)-4-methyl-2-phenyl-3a,4-dihydro-3H-furo[3,4-c]pyrazol-6-one | 1037025-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aS,4S)-4-methyl-2-phenyl-3a,4-dihydro-3H-furo[3,4-c]pyrazol-6-one
• CAS: 1037025-59-4
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: PBDWIGJNNGFQPB-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-but-3-en-2-yl 2-chloro-2-(2-phenylhydrazineylidene)acetate 在 silver carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 96.0h， 以82%的产率得到(3aS,4S)-4-methyl-2-phenyl-3a,4-dihydro-3H-furo[3,4-c]pyrazol-6-one
  参考文献：
  名称：

  Enantiopure furo[3,4-c]pyrazole derivatives by intramolecular nitrilimine cycloaddition: a stereoselectivity rationale based upon MP2 calculations

  摘要：

  Silver carbonate treatment of hydrazonoyl chloride 4 promoted the in situ generation of the corresponding nitrilimine bearing a stereocentre at the alpha-position of the ethylenic dipolarophile. Intramolecular cycloaddition of the latter intermediate involves the formation of 4-(S)-methyl-6-oxo-3,3a,4,5-tetra hydro-furo[3,4-c]pyrazole derivatives with very good yield and diastereoselectivity. Full rationalization of the experimentally observed stereoselectivity has been pursued by means of MP2 calculations. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.007