9-Methoxy-1,4-phenanthrenedione | 153632-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9-Methoxy-1,4-phenanthrenedione
• 英文别名: 9-methoxyphenanthrene-1,4-dione
• CAS: 153632-92-9
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: XMMHVGOFNJVTGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-Methoxy-1,4-phenanthrenedione 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 3.0h， 以62%的产率得到2,3-Dichloro-9-methoxy-phenanthrene-1,4-dione
  参考文献：
  名称：

  Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them

  摘要：

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.

  DOI：

  10.1021/jo00110a036
• 作为产物：
  描述：

  (1,1-二甲氧基乙基)苯 在 吡啶 、 三甲基氯硅烷 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 35.0h， 生成 9-Methoxy-1,4-phenanthrenedione
  参考文献：
  名称：

  Diels-Alder Reactions of .alpha.-Substituted Styrenes with p-Benzoquinone

  摘要：

  DOI：

  10.1021/jo00086a046

文献信息

• Diels-Alder Reactions of .alpha.-Substituted Styrenes with p-Benzoquinone
  作者：Nikolaos D. Willmore、Diego A. Hoic、Thomas J. Katz

  DOI：10.1021/jo00086a046

  日期：1994.4
• Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them
  作者：Shuhao Shi、Thomas J. Katz、Bingwei V. Yang、Longbin Liu

  DOI：10.1021/jo00110a036

  日期：1995.3

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.