2-butyl-7-methyl-1,4-naphthoquinone | 140468-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-butyl-7-methyl-1,4-naphthoquinone
• 英文别名: 2-Butyl-7-methylnaphthalene-1,4-dione；2-butyl-7-methylnaphthalene-1,4-dione
• CAS: 140468-49-1
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: QIUQSWZBJFGBCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-己炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 ammonium cerium(IV) nitrate 、 硝酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.5h， 以42%的产率得到2-butyl-7-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  Approaching ambient temperatures in 1,2-DCE to deliver efficient intermolecular Dötz benzannulation processes

  摘要：

  Conditions have been developed that enable intermolecular Dotz benzannulations to be carried out under extremely mild conditions, using 1,2-DCE as the reaction solvent and without the requirement for any additional reaction promoters. The new protocols, at temperatures close to ambient, have been applied successfully to a range of internal and terminal alkynes with a series of aryl and alkenyl carbene complexes, resulting in good to high yields of the benzannulation products. The developed conditions did, however, return lower benzannulation yields when utilised with the traditionally more troublesome 2-furyl carbene complex. It was found that increased reaction temperatures in 1,2-DCE did deliver high yields for the processes with this heteroaryl species. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.088

文献信息

• Intramolecular Benzannulation Reactions of Chromium Siloxycarbene Complexes: Regiochemical Control and the "Xenochemical Effect" of Alkyne Additives
  作者：Michael F. Gross、M. G. Finn

  DOI：10.1021/ja00103a007

  日期：1994.11

  Acetylenic alcohols are attached to chromium oxycarbene fragments via dialkylsilicon linkages in convenient fashion to provide siloxycarbene complexes which undergo intramolecular benzannulation upon heating. Yields of alkynol-derived quinone products after oxidative workup increase markedly when the reactions are conducted in the presence of the ''external'' alkynes diphenylacetylene, 3-hexyne, or 1-hexyne. The action of alkyne additives, which participate in competitive intermolecular benzannulation to only a minor extent, is inhibited by donor solvent or carbon monoxide. Kinetics measurements demonstrate that the benzannulation reactions are initiated by dissociative CO loss. The alkyne additives are believed tb act by coordination to vinylcarbene intermediates produced by intramolecular alkyne insertion, consistent with previous suggestions. A carbon-tethered analogue was found to be unresponsive to the addition of external alkyne. Evidence for the reversible nature of alkyne insertion and the bimolecular decomposition of siloxycarbene complexes is discussed. The methodology provides products with complete regiospecificity regardless of the size of the tethered alkyne substituents, including those not directly accessible by intermolecular reactions of terminal alkynes.