2,3-Diethyl-6-methoxy-[1,4]naphthoquinone | 114649-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-Diethyl-6-methoxy-[1,4]naphthoquinone
• 英文别名: 2,3-Diethyl-6-methoxynaphthalene-1,4-dione
• CAS: 114649-61-5
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: GQELLVQANULKRA-UHFFFAOYSA-N

物化性质

• 沸点：
  403.5±45.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-己炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 ammonium cerium(IV) nitrate 作用下， 生成 2,3-Diethyl-6-methoxy-[1,4]naphthoquinone
  参考文献：
  名称：

  溶剂，螯合和浓度对卡宾铬配合物和乙炔的苯环化反应的影响

  摘要：

  一些铬卡宾络合物的（CO）的反应中5 CrC（OME）R（R = PH，Õ -OMePh，p -OMePh，ö -O-tBuPh，1-C 6 ħ 9，1-C 5 ħ 7 O）与各种乙炔（R'CCR检查2，R 1，R 2 = H，ME等，正镨，pH值，森达3）在低至高配位能力的溶剂中使用。简单的α，β-不饱和配合物的反应对苯环化产物的高选择性不受乙炔上溶剂或取代基变化的影响。芳基配合物与乙炔的反应对溶剂和乙炔的性质非常敏感。芳基配合物反应生成的苯甲环化产物的最高选择性和效率是配位能力低的溶剂。具有中等配位能力和小尺寸的溶剂对于与二取代的乙炔反应形成环丁烯酮具有很高的选择性。具有高配位能力的溶剂会产生最少的选择性反应，并产生大量的茚产物。一个o卡宾配合物的芳基取代基上的-甲氧基可在苯环化反应过程中螯合至金属中心，并且在乙腈中，改变产物分布，有利于环丁烯酮产物。（CO）取代的复合物的氨基，5 CrC（NME

  DOI：

  10.1016/0022-328x(87)80037-2

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.
• Substrate regulation of product distribution in the reactions of arylchromium carbene complexes with alkynes
  作者：Mary Ellen Bos、William D. Wulff、Ross A. Miller、Steven Chamberlin、Timothy A. Brandvold

  DOI：10.1021/ja00024a040

  日期：1991.11

  The reactions of arylcarbene complexes with alkynes were examined for six of the nine possible substitution patterns for mono- and dioxygenated aryl substituents of the carbene carbon. The product distributions were found to be highly dependent on a number of factors, including solvent, temperature, concentration of alkyne, and the nature of the aryl substituent. The product distributions were determined in nearly all cases for phenol and indene products and in some cases for furans, cyclobutenones, and cyclopentenediones, which were minor products in these reactions. The product distribution for the reaction of each arylcarbene complex was determined as a function of both temperature and alkyne concentration, since the combined product distribution profiles provided a much more sensitive measure of the relative influences of the aryl substituents on the reaction outcome. Furthermore, this distribution profile was determined for the reactions with 3-hexyne and I-pentyne for each carbene complex. A series of monosubstituted arylcarbene complexes were examined to identify the effects of oxygen substituents at various positions on the aryl ring. The m-methoxy group has no effect on the product distribution, whereas the o-methoxy group influences the distribution by its ability to chelate to the metal center and the p-methoxy group influences the distribution by its ability to donate electrons by resonance. The product distributions from the reactions of the 2,3-, 2,4-, and 2,5-dimethoxy complexes followed the profile expected from the simple sum of the profiles of the monomethoxyl complexes. In all cases where an effect was observed, higher concentrations of alkyne led to a higher selectivity for phenol over indene products. The dependence of the product distribution on the concentration of the alkyne substrate is suggested to be due to a process in which a second molecule of alkyne coordinates to the metal center and determines the chemical outcome of an intermediate that has covalently incorporated the first alkyne. It is further suggested that the special ability of an alkyne to display this effect is related to the ability of an alkyne to readily switch from a 2 to a 4 e- donor. This phenomenon of substrate regulation of product distribution is termed the allochemical effect, and a mechanistic explanation is developed that features this proposed process and that is refined to accommodate the observed effects of solvent, temperature, chelation, and steric and electronic effects that have been observed for the reaction of carbene complexes and alkynes.
• CHAN, KIN SHING;PETERSON, GLEN A.;BRANDVOLD, TIMOTHY A.;FARON, KATHERINE +, J. ORGANOMET. CHEM., 334,(1987) N 1-2, 9-56
  作者：CHAN, KIN SHING、PETERSON, GLEN A.、BRANDVOLD, TIMOTHY A.、FARON, KATHERINE +

  DOI：——

  日期：——