7-dimethylamino-11-(4'-propylphenyl)tricyclo[5.2.2.0^1,6]undec-10-en-9-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: 7-dimethylamino-11-(4'-propylphenyl)tricyclo[5.2.2.0^1,6]undec-10-en-9-one
• 英文别名: (1S,6S,7R)-7-(dimethylamino)-11-(4-propylphenyl)tricyclo[5.2.2.01,6]undec-10-en-9-one
• 化学式: C₂₂H₂₉NO
• 分子量: 323.478
• InChiKey: PFTYOJXVCDRHAG-BVSLBCMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-丙基苯乙炔 、 pentacarbonyl[(2E)-3-cyclohexenyl-3-dimethylamino-1-ethoxy-2-propen-1-ylidene]chromium 以 吡啶 为溶剂， 反应 64.0h， 以87%的产率得到7-dimethylamino-11-(4'-propylphenyl)tricyclo[5.2.2.0^1,6]undec-10-en-9-one
  参考文献：
  名称：

  Facile Synthesis of 7-Dimethylamino-endo-tricyclo[5.2.2.01,6]undec-10-en-9-ones

  摘要：

  Pentacarbonyl[(2E)-3-cyclohexenyl-3-dimethylamino-1-ethoxy-2-propen-1-ylidene]chromium (2) yields 7-dimethylamino-endo-tricyclo[5.2.2.0(1,6)]undec-10-en-9-ones 5 (15-88%, 12 examples) upon treatment with alkynes 3 in pyridine, most probably by a 6 pi -electrocyclization followed by a subsequent reductive elimination/intermolecular Diels-Alder reaction with the alkyne and eventual hydrolysis. The direct cyclization of 2 to the cyclohexane-annelated cyclopentadiene 6 is faster than the usual alkyne insertion of alpha,beta -unsaturated Fischer carbene complexes. The [4+2] cycloadditions of 7 and the added alkynes 3 occur with high degrees of regio- and complete diastereoselectivity.

  DOI：

  10.1002/1099-0690(200107)2001:13<2501::aid-ejoc2501>3.0.co;2-o