benz-1,4-phenanthrenequinone | 109699-80-1

• 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: benz-1,4-phenanthrenequinone
• 英文别名: benzo[c]phenanthrene-1,4-dione；Benzo[c]phenanthren-1,4-dion；benzo[g]phenanthrene-1,4-dione
• CAS: 109699-80-1
• 化学式: C₁₈H₁₀O₂
• 分子量: 258.276
• InChiKey: OJPQILIJRKPTNG-UHFFFAOYSA-N

物化性质

• 熔点：
  229.5-230 °C
• 沸点：
  499.5±45.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

SDS

反应信息

• 作为反应物：
  描述：

  benz-1,4-phenanthrenequinone 在 四氢呋喃 、 lithium aluminium tetrahydride 作用下， 生成 苯并-3,4-菲
  参考文献：
  名称：

  993.多环芳族化合物的合成。第一部分：醌与乙烯基萘和相关二烯的反应

  摘要：

  DOI：

  10.1039/jr9570004967
• 作为产物：
  描述：

  2-乙烯基萘 、 2-(p-tolylsulfinyl)-1,4-benzoquinone 以 甲苯 为溶剂， 20.0 ℃ 、1199.99 MPa 条件下， 反应 24.0h， 以48%的产率得到benz-1,4-phenanthrenequinone
  参考文献：
  名称：

  Improved Synthesis of 1,4-Phenanthrenequinones from Diels-Alder Cycloadditions of 2-(p-Tolylsulfinyl)-1,4-benzoquinone

  摘要：

  A wide range of substituted 1,4-phenanthrenequinones 5a-g and benz[c]- and benz[a]-1,4-phenanthrenequinones (5h) and (5i) were synthezised in one step through Diels-Alder cycloadditions of 2-(p-tolylsulfinyl)-1,4-benzoquinone 2 and vinylaromatic derivatives 1a-i under thermal and high pressure conditions in moderate to good yields (33-80%). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00505-4

文献信息

• Keto–enol equilibrium: stable tautomers of ortho-, meta-, and para-hydroquinones in large aromatics
  作者：Vincent Silber、Christophe Gourlaouen、Romain Ruppert

  DOI：10.1039/d4ra02202e

  日期：——

  the 1,4-hydroquinone and 1,4-dihydroxynaphthalene, the stable tautomers for the [4] and [6]helicenes were the aromatic diketones. These experimental results were corroborated by calculations. Additional calculations showed that these tautomeric species were indeed the stable forms of 1,4 and 1,3-hydroquinones when present in larger aromatics, in drastic contrast with 1,2-dihydroxy-aromatics (known as

  提出了以1,4-二甲氧基-[6]螺烯衍生物为原料合成[6]螺烯对醌。三溴化硼的去甲基化反应产生了意想不到的结果。分离出二酮互变异构形式，而不是预期的对氢醌。与1,4-氢醌和1,4-二羟基萘相反，[4]和[6]螺烯的稳定互变异构体是芳香族二酮。这些实验结果通过计算得到了证实。额外的计算表明，这些互变异构体确实是 1,4 和 1,3-氢醌存在于较大芳香族化合物中时的稳定形式，与 1,2-二羟基芳香族化合物（称为儿茶酚）形成鲜明对比。
• 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.