5-methoxybenzanthracene-7,12-dione | 59339-85-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: 5-methoxybenzanthracene-7,12-dione
• 英文别名: 5-methoxy-benz[a]anthracene-7,12-dione；5-Methoxy-benz[a]anthracen-7,12-dion；5-Methoxi-benz-anthracen-7,12-chinon；5-methoxybenzo[a]anthracene-7,12-dione
• CAS: 59339-85-4
• 化学式: C₁₉H₁₂O₃
• 分子量: 288.302
• InChiKey: XQERYVSNAUVIAY-UHFFFAOYSA-N

物化性质

• 熔点：
  188-189 °C(Solv: ethanol (64-17-5))
• 沸点：
  518.8±39.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

上下游信息

反应信息

• 作为反应物：
  描述：

  5-methoxybenzanthracene-7,12-dione 在 sodium hydroxide 、 三氯化铝 、 sodium dithionite 、 sodium chloride 作用下， 生成 5-hydroxy-6-methyl-benz[a]anthracene-7,12-dione
  参考文献：
  名称：

  阮内镍还原-VIII：1：2-苯并蒽及其3'-甲基和4-甲基衍生物的合成

  摘要：

  通过阮内镍还原1：2-苯并蒽醌和4'-氯3'-甲基-1：2-苯并蒽醌的无色衍生物的硫酸酯制得1：2-苯并蒽和3'-甲基衍生物，然后脱氢。通过甲醛，亚硫酸氢钠和氢氧化钠溶液在4-位甲基化3-羟基-1：2-苯并蒽醌（Marschalk反应）。通过阮内镍还原3：9：10-三羟基-4-甲基-1：2-苯并蒽的三硫酸酯和生成的六氢-4-甲基-1：2来同时还原核羟基和醌基团-苯并蒽被脱氢成4-甲基-1：2-苯并蒽。3：4：9的准备：

  DOI：

  10.1016/0040-4020(59)80023-5
• 作为产物：
  描述：

  5-甲氧基-12H-苯并[a]蒽-7-酮 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 5-methoxybenzanthracene-7,12-dione
  参考文献：
  名称：

  Fieser; Dietz, Journal of the American Chemical Society, 1929, vol. 51, p. 3144

  摘要：

  DOI：

文献信息

• LDA (Lithium Diisopropylamide) Mediated Reactions of 1-Naphthalynes with Lithiated Acetonitriles and 1,4-Dipolar Nucleophilic Anions
  作者：Edward R. Biehl、A. Rakeeb Deshmukh、Mahesh Dutt

  DOI：10.1055/s-1993-25963

  日期：——

  3-Bromo-2-methoxy-(5) and 3-bromo-2-methoxy-6-methylnaphthalene (6) yield 1-naphthalyne intermediates which react with various α-lithiated nitriles 10 to afford both rearranged 1-arylmethyl- or 1-hetarylmethyl-3-methoxynaphthalene-2-carbonitriles 11 and 12, respectively, and α-naphthylated aryl- or hetarylacetonitriles 13 and 14, respectively. Product distributions 11:13 favoring rearranged nitriles (65:35-90:10) were obtained from LDA-mediated reactions of 5 with arylacetonitriles 9a, b and thiopheneaceto-nitriles 9c, d. Similar treatment of 6 with 9a-d gave product distributions 12:14 heavily in favor of rearranged nitriles (> 90:10) presumably due to the ability of the additional 7-methyl group to increase the rate of cyclization of the initial aryne-nitrile anion adduct, the crucial step in the rearrangement pathway. However treatment of either 5 or 6 with α-lithiated pyridylacetonitriles 9e, f or 2-benzimidazolylacetonitrile (9g) gave product distributions 11:13 or 12:14, respectively, heavily in favor of α-naphthylated acetonitriles (30: 70 > 10: 90). Additionally, several precursors to methoxy-substituted 1-naphthalynes 5,19 and 20 were found to undergo cycloaddition with the dipolar nucleophilic precursors 3-cyanophthalide (17) and α-cyano-o-tolunitrile (21) to give angularly substituted benz[α]anthracene derivatives 18, 22.

  3-溴-2-甲氧基-（5）和3-溴-2-甲氧基-6-甲基萘（6）生成的1-萘基中间体与各种α-锂化腈10反应，分别产生重排的1-芳基甲基或1-杂环芳基甲基-3-甲氧基萘-2-碳腈11和12，以及α-萘基化的芳基或杂环乙腈13和14。从LDA介导的5与芳基乙腈9a、b以及噻吩乙腈9c、d的反应中，获得了重排腈的产物分布11:13，更倾向于重排腈（65:35-90:10）。对6与9a-d进行类似处理，得到的产物分布12:14严重偏向重排腈（> 90:10），这可能是由于额外的7-甲基基团能够增加初始芳烯-腈阴离子加合物的环化速率，这是重排途径中的关键步骤。然而，5或6与α-锂化的吡啶乙腈9e、f或2-苯并咪唑基乙腈（9g）的反应，分别得到的产物分布11:13或12:14，则严重偏向α-萘基化的乙腈（30:70 > 10:90）。此外，几个甲氧基取代的1-萘基前驱体5、19和20被发现与双极性亲核前驱体3-氰基邻苯二甲酸酯（17）和α-氰基-o-甲苯腈（21）发生环加成，生成角度取代的苯[α]蒽衍生物18、22。
• Maruyama, Kazuhiro; Tai, Seiji; Tojo, Masahiro, Heterocycles, 1981, vol. 16, # 11, p. 1963 - 1974
  作者：Maruyama, Kazuhiro、Tai, Seiji、Tojo, Masahiro、Otsuki, Tetsuo

  DOI：——

  日期：——
• Backhouse et al., Journal of the Chemical Society, 1955, p. 91,94
  作者：Backhouse et al.

  DOI：——

  日期：——
• Human–computer interface design issues for a multi-cultural and multi-lingual English speaking country — Botswana
  作者：E.A Onibere、S Morgan、E.M Busang、D Mpoeleng

  DOI：10.1016/s0953-5438(00)00052-7

  日期：2001.4

  This paper reports on research carried out to determine whether a localised interface is preferred by users in a multi-cultural and multi-lingual country where a non-local language is nationally used,. We attempted to discover whether local symbols are more acceptable to users as icons and also whether the current phrases used in menus and icon descriptions are clearly understood by the various communities.A survey was conducted nation-wide among computer end-users in Botswana. The results indicate an overwhelming desire from users for a localised interface. However, there appears to be little need for localised icons and no agreement as to which language to use for text-based interfaces. (C) 2001 Elsevier Science B.V. All rights reserved.
• Bichl Edward R., Deshmukh A. Rakeeb, Dutt Mahesh, Synthesis, (1993) N 9, S 885-888
  作者：Bichl Edward R., Deshmukh A. Rakeeb, Dutt Mahesh

  DOI：——

  日期：——