2-n-Propyl-6-methylbenzoquinone | 90150-43-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-n-Propyl-6-methylbenzoquinone
• 英文别名: 2-methyl-6-propylcyclohexa-2,5-diene-1,4-dione
• CAS: 90150-43-9
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: JBABTBHBCDYHMN-UHFFFAOYSA-N

物化性质

• 沸点：
  239.2±15.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-Dimethylamino-2-methyl-6-propyl-phenol 在 ammonium cerium(IV) nitrate 作用下， 生成 2-n-Propyl-6-methylbenzoquinone
  参考文献：
  名称：

  Phenol Formation from the Reactions of Amino-Stabilized Alkenyl Fischer Carbene Complexes

  摘要：

  The first examples of phenol formation from the reactions of amino-stabilized alpha,beta P-unsaturated Fischer carbene complexes with alkynes are reported. A series of four dimethylamino complexes [(CO)(5)Cr=C(NMe(2))R; 19, R = cyclohexenyl; 26, R = trans-propenyl; 27, R = trans-styryl; 30, R = isopropenyl] were examined with both internal and external alkynes. Their reactions with internal alkynes typically produced low yields of complex mixtures of products and were not synthetically useful. In contrast, their reactions with terminal alkynes were remarkably different giving good yields of 4-(dimethylamino)phenols, and in the presence of a trapping agent, good yields of the arene chromium tricarbonyl complexes of the protected 4-(dimethylamino)phenols. The selectivity for phenol formation was found to be greatest for reactions performed in noncoordinating solvents and at higher concentrations. In contrast, and as expected, the reaction of the aryl complex 45 [(CO)(5)Cr=C(NMe(2))Ph] with 1-pentyne did not produce any six-membered ring product in DMF, THF, or benzene. An interesting solvent dependence was observed for this reaction where lactam 49 was the exclusive product in benzene and the indanone 46 was the exclusive product in DMF.

  DOI：

  10.1021/jo00119a039

文献信息

• Benzannulation of .alpha.,.beta.-unsaturated Fischer carbene complexes with acetylenes
  作者：William D. Wulff、Kin Shing Chan、Peng Cho Tang

  DOI：10.1021/jo00186a046

  日期：1984.6
• Contrasteric Regiochemical Incorporation of Stannylacetylenes in the Benzannulation Reaction
  作者：Steven Chamberlin、Marcey L. Waters、William D. Wulff

  DOI：10.1021/ja00086a047

  日期：1994.4
• WULFF, W. D.;CHAN, KIN-SHING;TANG, PENG-CHO, J. ORG. CHEM., 1984, 49, N 12, 2293-2295
  作者：WULFF, W. D.、CHAN, KIN-SHING、TANG, PENG-CHO

  DOI：——

  日期：——