6-hydroxy-1,2,3,4-tetrahydrotetraphene-7,12-dione | 133961-69-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: 6-hydroxy-1,2,3,4-tetrahydrotetraphene-7,12-dione
• 英文别名: 6-Hydroxy-1,2,3,4-tetrahydrobenzo[a]anthracene-7,12-dione
• CAS: 133961-69-0
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: OPRBDVKIODCDQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-1,2,3,4-tetrahydrotetraphene-7,12-dione 在 甲酸 、 sodium dithionite 、 oxone||potassium monopersulfate triple salt 、 四丁基溴化铵 、 碳酸氢钠 、 potassium carbonate 、 钯 、 potassium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 20.33h， 生成 7-hydroperoxy-7,11b-dimethoxy-3,4,7,11b-tetrahydro-1H-tetrapheno[12-cd][1,2]dioxol-6(2H)-one
  参考文献：
  名称：

  Selective Oxidative Dearomatization of Angular Tetracyclic Phenols by Controlled Irradiation under Air: Synthesis of an Angucyclinone-Type Double Peroxide with Anticancer Properties

  摘要：

  Angular tetracyclic p-peroxyquinols, p-quinols, and a pentacyclic double peroxide, showing anticancer properties, were synthesized from the corresponding phenols by an environmentally friendly solvent- and wavelength-controlled irradiation under air in the absence of an external photosensitizer.

  DOI：

  10.1021/acs.orglett.8b02515
• 作为产物：
  描述：

  5,6,7,8-四氢-2-萘酚 在 pyridinium polyhydrogen fluoride 、 碘苯二乙酸 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 6-hydroxy-1,2,3,4-tetrahydrotetraphene-7,12-dione
  参考文献：
  名称：

  4-氟环己基2,5-二壬烯作为豪瑟环空的新受体

  摘要：

  引入4-氟环己基2,5-二壬烯作为豪瑟环化反应的新受体。在相应的甲氧基类似物不能进行环合的情况下，前者可以与苯磺酰邻苯二甲酸酯一起顺畅地进行，从而以高收率提供蒽醌。涉及立体效应来解释甲氧基类似物的惰性。

  DOI：

  10.1016/j.tetlet.2007.01.159

文献信息

• Total synthesis of BE-23254, a chlorinated angucycline antibiotic
  作者：Satyajit Dey、Dipakranjan Mal

  DOI：10.1016/j.tetlet.2005.06.062

  日期：2005.8

  The first synthesis of BE-23254, an unusual angucycline antibiotic, is reported. It involves regioselective condensation of naphthalenone 4 and chlorine-containing isobenzofuranone 16 as the key step.

  据报道，BE-23254是一种罕见的安古环素抗生素的首次合成。这是关键步骤，包括萘酮4和含氯异苯并呋喃酮16的区域选择性缩合。
• 3-(Phenylthio)phthalide: an Expedient Reagent in Phthalide Annulation
  作者：Sujit K. Ghorai、Harendra N. Roy、Mousumi Bandopadhyay、Dipakranjan Mal

  DOI：10.1039/a802608d

  日期：——

  3-(Phenylthio)phthalide 4 is more readily accessible than the established reagents 1 and 2 and can be engaged in phthalide annulation with comparable efficacy.

  3-(苯硫基)邻苯二甲酸 4 比现有的试剂 1 和 2 更容易获得，并能以相当的效果参与邻苯二甲酸环化反应。
• Synthesis of chlorine-containing angucycline BE-23254 and its analogs
  作者：Dipakranjan Mal、Satyajit Dey

  DOI：10.1016/j.tet.2006.07.090

  日期：2006.10

  The total synthesis of BE-23254, an unusual angucycline antibiotic is reported. This is achieved by adopting a Hauser annulation and a DDQ-promoted aromatization as the key steps. The strategy has been generalized for the synthesis of several analogs of the target molecule. A regioselective preparation of chlorine-containing phenols is also described. (c) 2006 Elsevier Ltd. All rights reserved.
• A rapid access to hydroxylated benz[a]anthraquinones: Hypervalent iodine oxidation of β-naphthols
  作者：Dipakranjan Mal、Harendra N. Roy、Nirmal K. Hazra、Susanta Adhikari

  DOI：10.1016/s0040-4020(96)01119-2

  日期：1997.2

  Anionic annulation of phthalide sulfones 3 with quinone monoketals 6, accessible by phenyliodonium diacetate oxidation of naphthols 5, offers a high yielding regiospecific entry to benz[a]anthraquinones 8. Similar annulation of cyanophthalide 13 with 12, followed by photooxygenation of 14 results in a complementary route to the basic skeleton 15 of nonaromatic A-ring angucyclines. (C) 1997, Published by Elsevier Science Ltd.
• Synthesis of 1-amino- and 1-hydroxy-9,10-anthraquinone derivatives based on reaction sequences between 2-acetyl-1,4-naphthoquinone and enamines
  作者：Kazuhiro Kobayashi、Masaharu Uchida、Shinya Watanabe、Atsushi Takanohashi、Miyuki Tanmatsu、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1016/s0040-4039(00)00168-4

  日期：2000.4

  2-Acetyl-1,4-naphthoquinone was treated with pyrrolidine (or morpholine) enamines, derived from cyclic and acyclic ketones, in DMF at room temperature for 24-72 h to afford 3,4-disubstituted 1-pyrrolidino(or morpholino)-9,10-anthraquinones. On the other hand, when the treatment of 2-acetyl-1,4-naphthoquinone with enamines for 2 min was followed by addition of water and heating at 100 degrees C for 2 h, the corresponding 1-hydroxy-9,10-naphthoquinone derivatives were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.