9-(2-Butoxyethoxy)-1,4-phenanthrenedione | 153632-93-0

• 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-(2-Butoxyethoxy)-1,4-phenanthrenedione
• 英文别名: 9-(2-butoxyethoxy)phenanthrene-1,4-dione
• CAS: 153632-93-0
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: XJYHYNXJNOQMNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(2-Butoxyethoxy)-1,4-phenanthrenedione 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 3.5h， 以64%的产率得到9-(2-Butoxy-ethoxy)-2,3-dichloro-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：

  2-甲基-2-苯基-1,3-二氧戊环 在 氢氧化钾 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 二甲基亚砜 、 甲苯 、 乙腈 为溶剂， 反应 52.17h， 生成 9-(2-Butoxyethoxy)-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.