(3aRS,6aSR,3E)-6,6,6a-trimethyl-3-[(phenylamino)methylidene]hexahydrocyclopenta[b]furan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aRS,6aSR,3E)-6,6,6a-trimethyl-3-[(phenylamino)methylidene]hexahydrocyclopenta[b]furan-2-one
• 英文别名: (3E,3aS,6aR)-3-(anilinomethylidene)-6,6,6a-trimethyl-4,5-dihydro-3aH-cyclopenta[b]furan-2-one
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: NGEAKWJZKLRTDU-RGCHEUQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,4E,5S)-4-[(dimethylamino)methylidene]-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one 在 氢氟酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (3aRS,6aSR,3E)-6,6,6a-trimethyl-3-[(phenylamino)methylidene]hexahydrocyclopenta[b]furan-2-one
  参考文献：
  名称：

  Synthesis and transformations of new dihydro-β-campholenolactone derivatives

  摘要：

  The reaction of xenon difluoride with enamino lactone 3 furnished the new alpha-fluoro aldehyde 7, whereas reaction of 3 with anhydrous HF led to racemic dihydro-beta-campholenolactone 6. Acid-catalysed rearrangement of alpha-ethylidenclactone 4 proceeded with retention of configuration to give beta-campholenolactone 8. Nitrosation of the novel bicyclic enamino lactone 6 afforded the corresponding oxime 9, while acid-catalysed treatment with primary amines, 2-methyl-1H-indole, potassium cyanide and hydrazine hydrochloride, furnished the dimethylamine substitution products 11-13 and the 'ring switched' product 14. The structures were determined by 2D NMR techniques, NOESY spectroscopy and X-ray diffraction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.007