2,6-dimethoxy-3-methylacetophenone | 857565-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dimethoxy-3-methylacetophenone
• 英文别名: 1-(2,6-dimethoxy-3-methyl-phenyl)-ethanone；1-(2,6-Dimethoxy-3-methyl-phenyl)-aethanon；1-(2,6-Dimethoxy-3-methylphenyl)ethan-1-one；1-(2,6-dimethoxy-3-methylphenyl)ethanone
• CAS: 857565-00-5
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: WCGLWSNNYLQSKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  20-22 °C
• 沸点：
  294.9±35.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-dimethoxy-3-methylacetophenone 在 lithium aluminium tetrahydride 、 silica gel 、 丙酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 46.25h， 生成 3-(2,6-dimethoxy-3-methylphenyl)-3-methylpent-4-enal
  参考文献：
  名称：

  Structure revision of HM-3, an aromatic sesquiterpene isolated from the phytopathogenic fungus Helicobasidium mompa. First total syntheses of HM-3 and HM-4

  摘要：

  The first total syntheses of HM-3 and HM-4 aromatic sesquiterpenes isolated from the phytopathogenic fungus Helicobasidium mompa, have been accomplished. The structure assigned to the sesquiterpene HM-3 was found to be incorrect by total synthesis. A Claisen rearrangement-RCM reaction based strategy was employed for the total synthesis of the aromatic sesquiterpene HM-4 (cuparene-1,2-diol), which on selective monoacetylation established the structure of HM-3, a cuparene derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.062
• 作为产物：
  描述：

  2,4-二甲氧基甲苯 在 正丁基锂 、 四甲基乙二胺 、 silica gel 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 78.0h， 生成 2,6-dimethoxy-3-methylacetophenone
  参考文献：
  名称：

  Structure revision of HM-3, an aromatic sesquiterpene isolated from the phytopathogenic fungus Helicobasidium mompa. First total syntheses of HM-3 and HM-4

  摘要：

  The first total syntheses of HM-3 and HM-4 aromatic sesquiterpenes isolated from the phytopathogenic fungus Helicobasidium mompa, have been accomplished. The structure assigned to the sesquiterpene HM-3 was found to be incorrect by total synthesis. A Claisen rearrangement-RCM reaction based strategy was employed for the total synthesis of the aromatic sesquiterpene HM-4 (cuparene-1,2-diol), which on selective monoacetylation established the structure of HM-3, a cuparene derivative. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.062

文献信息

• Mold Metabolites. IV. The Ultraviolet Absorption Spectra of Certain Aromatic Hydroxyketones
  作者：Donald J. Cram、F. W. Cranz

  DOI：10.1021/ja01157a150

  日期：1950.1
• Structure revision of HM-3, an aromatic sesquiterpene isolated from the phytopathogenic fungus Helicobasidium mompa. First total syntheses of HM-3 and HM-4
  作者：A. Srikrishna、P.C. Ravikumar

  DOI：10.1016/j.tet.2006.07.062

  日期：2006.10

  The first total syntheses of HM-3 and HM-4 aromatic sesquiterpenes isolated from the phytopathogenic fungus Helicobasidium mompa, have been accomplished. The structure assigned to the sesquiterpene HM-3 was found to be incorrect by total synthesis. A Claisen rearrangement-RCM reaction based strategy was employed for the total synthesis of the aromatic sesquiterpene HM-4 (cuparene-1,2-diol), which on selective monoacetylation established the structure of HM-3, a cuparene derivative. (c) 2006 Elsevier Ltd. All rights reserved.