2-methyl-2-(4-phenylbut-3-ynyl)cyclopentane-1,3-dione | 166517-16-4

• 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: 2-methyl-2-(4-phenylbut-3-ynyl)cyclopentane-1,3-dione
• 英文别名: 2-methyl-2-(4-phenyl-3-butynyl)-1,3-cyclopentanedione；2-Methyl-2-(4-phenylbut-3-ynyl)cyclopentane-1,3-dione
• CAS: 166517-16-4
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: COSSXBFJHKBLJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(4-phenylbut-3-ynyl)cyclopentane-1,3-dione 在 silver hexafluoroantimonate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 以89%的产率得到6-benzoyl-6a-methyl-3,5,6,6a-tetrahydro-2H-pentalen-1-one
  参考文献：
  名称：

  Alkynes as Synthetic Equivalents to Stabilized Wittig Reagents:  Intra- and Intermolecular Carbonyl Olefinations Catalyzed by Ag(I), BF₃, and HBF₄

  摘要：

  The first use of cationic silver (AgSbF4) as a catalyst for intra- and intermolecular alkyne-carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Bronsted acid (HBF4) and Lewis acid (BF3) catalyst systems is made. Notably, intermolecular coupling proceeds stereoselectively to afford the corresponding trisubstituted enones as single geometrical isomers. This transformation represents a completely atom economical alternative to the use of stabilized Wittig reagents in carbonyl olefination and may be viewed as a formal alkyne-carbonyl metathesis.

  DOI：

  10.1021/ol050838x
• 作为产物：
  描述：

  碘苯 、 2-methyl-2-(3-butynyl)-1,3-cyclopentanedione 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二乙胺 作用下， 反应 16.0h， 以61%的产率得到2-methyl-2-(4-phenylbut-3-ynyl)cyclopentane-1,3-dione
  参考文献：
  名称：

  Additive and Medium Effects on Lewis Acid-Promoted Cationic .pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones

  摘要：

  The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored.

  DOI：

  10.1021/jo00107a012

文献信息

• Additive and Medium Effects on Lewis Acid-Promoted Cationic .pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones
  作者：Aaron Balog、Steven V. Geib、Dennis P. Curran

  DOI：10.1021/jo00107a012

  日期：1995.1

  The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored.
• Alkynes as Synthetic Equivalents to Stabilized Wittig Reagents:  Intra- and Intermolecular Carbonyl Olefinations Catalyzed by Ag(I), BF₃, and HBF₄
  作者：Jong Uk Rhee、Michael J. Krische

  DOI：10.1021/ol050838x

  日期：2005.6.1

  The first use of cationic silver (AgSbF4) as a catalyst for intra- and intermolecular alkyne-carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Bronsted acid (HBF4) and Lewis acid (BF3) catalyst systems is made. Notably, intermolecular coupling proceeds stereoselectively to afford the corresponding trisubstituted enones as single geometrical isomers. This transformation represents a completely atom economical alternative to the use of stabilized Wittig reagents in carbonyl olefination and may be viewed as a formal alkyne-carbonyl metathesis.