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。
• 4-Fluorocyclohexa-2,5-dienones as new acceptors for the Hauser annulation
  作者：Pallab Pahari、Bidyut Senapati、Dipakranjan Mal

  DOI：10.1016/j.tetlet.2007.01.159

  日期：2007.4

  4-Fluorocyclohexa-2,5-dienones are introduced as new acceptors for the Hauser annulation. In cases where the corresponding methoxy analogs fail to undergo annulation, the former smoothly do so with phenylsulfonyl phthalides to furnish anthraquinones in good yields. Steric effects are implicated to explain the inertness of the methoxy analogs.

  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。
• 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.