2-(2-Hydroxy-ethyl)-3,6-dimethyl-[1,4]naphthoquinone | 143887-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-Hydroxy-ethyl)-3,6-dimethyl-[1,4]naphthoquinone
• 英文别名: 2-(2-Hydroxyethyl)-3,6-dimethylnaphthalene-1,4-dione；2-(2-hydroxyethyl)-3,6-dimethylnaphthalene-1,4-dione
• CAS: 143887-54-1
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: NEVLSFLOKDZVHI-UHFFFAOYSA-N

物化性质

• 沸点：
  424.4±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-(2-Hydroxy-ethyl)-3,6-dimethyl-[1,4]naphthoquinone 、 alkaline earth salt of/the/ methylsulfuric acid 在 2,6-DTBT 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Intramolecular Benzannulation Reactions of Chromium Siloxycarbene Complexes: Regiochemical Control and the "Xenochemical Effect" of Alkyne Additives

  摘要：

  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.

  DOI：

  10.1021/ja00103a007
• 作为产物：
  描述：

  3-戊炔-1-醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 ammonium cerium(IV) nitrate 、 3-己炔 、 硝酸 、 二氯二甲基硅烷 作用下， 生成 2-(2-Hydroxy-ethyl)-3,6-dimethyl-[1,4]naphthoquinone 、 2,3-diethyl-6-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  Intramolecular Benzannulation Reactions of Chromium Siloxycarbene Complexes: Regiochemical Control and the "Xenochemical Effect" of Alkyne Additives

  摘要：

  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.

  DOI：

  10.1021/ja00103a007

文献信息

• Intramolecular benzannulation reactions of manganese carbene complexes
  作者：Bonnie L. Balzer、Martine Cazanoue、M. G. Finn

  DOI：10.1021/ja00048a076

  日期：1992.10

  Here we report that intramolecular benzannulation reactions of siloxycarbene compounds of manganese bearing tethered alkynes produce functionalized naphtoquinones in efficient fashion with complete regioselectivity under photochemical conditions.

  在这里，我们报告了含锰系链炔烃的硅氧卡宾化合物的分子内苯环化反应在光化学条件下以完全区域选择性的有效方式产生官能化的萘醌。
• 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.