1,4-dimethyl-7-(1-methylethyl)-3-(3-oxobutyl)azulene | 685879-07-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,4-dimethyl-7-(1-methylethyl)-3-(3-oxobutyl)azulene
• 英文别名: 4-[3,8-Dimethyl-5-(propan-2-yl)azulen-1-yl]butan-2-one；4-(3,8-dimethyl-5-propan-2-ylazulen-1-yl)butan-2-one
• CAS: 685879-07-6
• 化学式: C₁₉H₂₄O
• 分子量: 268.399
• InChiKey: GEQJKPQBZYOBGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(1-guaiazulenyl)but-3-en-2-one 在 高氯酸 、 环庚三烯 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以50.4%的产率得到1,4-dimethyl-7-(1-methylethyl)-3-(3-oxobutyl)azulene
  参考文献：
  名称：

  Novel Metal-Free Hydrogenation of the Carbon−Carbon Double Bond in Azulenoid Enones by Use of Cycloheptatriene and Protic Acid

  摘要：

  [GRAPHICS]An efficient method for the hydrogenation of the carbon-carbon double bond in azulenoid and aromatic fused azulenoid enones without the use of hydrogen and a metal catalyst is reported. Treatment of a variety of azulenoid enones with cycloheptatriene and a protic acid in acetonitrile gave the corresponding, beta-azulenyl ketone derivatives in excellent to moderate yield. In this reaction, cycloheptatriene acts as a hydride donor.

  DOI：

  10.1021/ol0611402

文献信息

• Gold(III) Chloride‐Catalyzed Addition Reactions of Electron‐Rich Arenes to Methyl Vinyl Ketone
  作者：Gerald Dyker、Enrico Muth、A. Stephen K. Hashmi、Li Ding

  DOI：10.1002/adsc.200303098

  日期：2003.11

  For the reaction of α,β-unsaturated ketones with electron-rich arenes catalyzed by gold(III) chloride both, a Friedel–Crafts-type mechanism and an initial metallation, are evaluated. Gold(III) chloride has proven to be an efficient catalyst under very moderate reaction conditions, however, in the case of sterically demanding products HBF4 turned out to be the superior catalyst.

  对于α，β-不饱和酮与氯化金（III）催化的富电子芳烃的反应，都评估了Friedel-Crafts型机理和初始金属化。在非常适中的反应条件下，氯化金（III）已被证明是一种有效的催化剂，但是，在空间要求严格的产品中，HBF 4被证明是优良的催化剂。
• Novel Metal-Free Hydrogenation of the Carbon−Carbon Double Bond in Azulenoid Enones by Use of Cycloheptatriene and Protic Acid
  作者：Takatomo Kimura、Tohru Takahashi、Mitsuko Nishiura、Kimiaki Yamamura

  DOI：10.1021/ol0611402

  日期：2006.7.1

  [GRAPHICS]An efficient method for the hydrogenation of the carbon-carbon double bond in azulenoid and aromatic fused azulenoid enones without the use of hydrogen and a metal catalyst is reported. Treatment of a variety of azulenoid enones with cycloheptatriene and a protic acid in acetonitrile gave the corresponding, beta-azulenyl ketone derivatives in excellent to moderate yield. In this reaction, cycloheptatriene acts as a hydride donor.