Spiro[3H-2-benzopyran-3,1'-cyclohexan]-1(4H)-one, 5,6,7,8-tetrahydro-4-methylene-

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Spiro[3H-2-benzopyran-3,1'-cyclohexan]-1(4H)-one, 5,6,7,8-tetrahydro-4-methylene-
• 英文别名: 4-methylidenespiro[5,6,7,8-tetrahydroisochromene-3,1'-cyclohexane]-1-one
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: UDVPJDXTYDXRCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己乙炔 、 2-bromocyclohex-1-enecarboxylic acid 在 palladium diacetate 、 四丁基氯化铵 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以53%的产率得到Spiro[3H-2-benzopyran-3,1'-cyclohexan]-1(4H)-one, 5,6,7,8-tetrahydro-4-methylene-
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Allenes Using Functionally Substituted Vinylic Halides

  摘要：

  Palladium catalyzes the regio-and stereoselective annulation of allenes by vinylic halides bearing alcohol-, amine-, sulfonamide-, carboxylic acid-, carboxamide-and carbanion-stabilizing groups to produce a variety of five-and six-membered-ring unsaturated heterocycles and carbocycles. The reaction appears to proceed by vinylic palladium formation and addition to the allene, followed by intramolecular nucleophilic displacement of the palladium. Six-membered rings are formed more readily than five-membered rings. The regioselectivity is generally high, with vinylic halides bearing alcohol, carboxylic acid, or carboxamide groups affording predominantly the product of intramolecular attack on the more substituted end of the pi-allylpalladium intermediate, while amines and carbanions attack quite selectively at the less substituted end of the pi-allylpalladium intermediate. Vinylic halides bearing tosylamides afford mixtures of regioisomers, where the predominant six-membered ring product arises by attack on the less substituted end of the allene, while the major five-membered ring products involve addition to the more substituted end of the allene.

  DOI：

  10.1021/jo9717245