2-hydroxyethyl-3-methyl-1,4-naphthoquinone | 76670-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxyethyl-3-methyl-1,4-naphthoquinone
• 英文别名: 2-(2-hydroxyethyl)-3-methylnaphthalene-1,4-dione
• CAS: 76670-45-6
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: XICWGGRIGJUNJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl-3-methyl-1,4-naphthoquinone 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以92%的产率得到2-methyl-3-(2-oxoethyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Laser photochemistry: trapping of quinone-olefin preoxetane intermediates with molecular oxygen and chemistry of the resulting 1,2,4-trioxanes

  摘要：

  DOI：

  10.1021/ja00380a018
• 作为产物：
  描述：

  2-(3-methyl-1,4-dimethoxynaphthalen-2-yl) ethanol 在 silver(II) oxide 、 硝酸 作用下， 以 1,4-二氧六环 为溶剂， 以90%的产率得到2-hydroxyethyl-3-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  Laser photochemistry: The wavelength dependent oxidative photodegradation of vitamin K analogs

  摘要：

  DOI：

  10.1016/s0040-4039(00)78714-4

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.
• Laser photochemistry: trapping of quinone-olefin preoxetane intermediates with molecular oxygen and chemistry of the resulting 1,2,4-trioxanes
  作者：R. Marshall Wilson、Stephen W. Wunderly、Thomas F. Walsh、Arlene K. Musser、Russell Outcalt、Fiona Geiser、Stephen K. Gee、Wayne Brabender、Lario Yerino

  DOI：10.1021/ja00380a018

  日期：1982.8
• Laser photochemistry: The wavelength dependent oxidative photodegradation of vitamin K analogs
  作者：R.Marshall Wilson、Thomas F. Walsh、Stephen K. Gee

  DOI：10.1016/s0040-4039(00)78714-4

  日期：1980.1