2,3-二甲氧基-6-甲基蒽-9,10-二酮 | 105706-01-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 2,3-二甲氧基-6-甲基蒽-9,10-二酮
• 英文名称: 2,3-dimethoxy-6-methylanthracene-9,10-dione
• 英文别名: 2,3-dimethoxy-6-methyl-9,10-anthraquinone；2,3-dimethoxy-6-methylanthraquinone；6-methyl hystazarin-methylether；9,10-Anthracenedione, 2,3-dimethoxy-6-methyl-
• CAS: 105706-01-2
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: GNOSWHOGNRQXKM-UHFFFAOYSA-N

物化性质

• 沸点：
  474.1±45.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 4-(3,4-dimethoxyphenyl)-4-oxobut-2-ynoate 在 硫酸 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 生成 2,3-二甲氧基-6-甲基蒽-9,10-二酮
  参考文献：
  名称：

  Synthesis of Fluorenone and Anthraquinone Derivatives from Aryl- and Aroyl-Substituted Propiolates

  摘要：

  Fluorenone derivatives were generated from aryl-substituted propiolates via a cobalt-catalyzed Diels-Alder reaction/DDQ-oxidation and Friedel-Crafts-type cyclization. Several functional groups are tolerated, and good to excellent overall yields (up to 89%) could be achieved. For the synthesis of anthraquinone derivatives, aroyl-substituted propiolates were applied in a zinc iodide catalyzed Die Is Alder reaction with 1,3-dienes. The subsequent DDQ oxidation and Friedel-Crafts-type cyclization led to symmetrical as well as some unsymmetrical anthraquinones in good to excellent yields of up to 87% over the three-step reaction sequence.

  DOI：

  10.1021/ol4023276

文献信息

• Palladium-Catalyzed Direct Acylation: One-Pot Relay Synthesis of Anthraquinones
  作者：Gedu Satyanarayana、Basuli Suchand

  DOI：10.1055/s-0037-1610296

  日期：2019.2

  anthraquinones via one-pot relay process, is presented. The first acylation was feasible under [Pd]-catalyzed intermolecular direct acylation reaction, while, the second acylation was accomplished by using intramolecular Friedel–Crafts acylation. Notably, benchtop aldehydes have been utilized as non-toxic acylation agents in the key [Pd]-catalyzed acylation. A bis-acylation strategy to access functionalized anthraquinones

  摘要 提出了一种双酰化策略，可通过一锅接力过程获得功能化的蒽醌。在[Pd]催化的分子间直接酰化反应下，第一次酰化是可行的，而第二次酰化是通过使用分子内Friedel-Crafts酰化来完成的。值得注意的是，台式醛已在关键的[Pd]催化的酰化反应中用作无毒的酰化剂。 提出了一种双酰化策略，可通过一锅接力过程获得功能化的蒽醌。在[Pd]催化的分子间直接酰化反应下，第一次酰化是可行的，而第二次酰化是通过使用分子内Friedel-Crafts酰化来完成的。值得注意的是，台式醛已在关键的[Pd]催化的酰化反应中用作无毒的酰化剂。
• An anthraquinone from Hedyotis diffusa
  作者：Tong-Ing Ho、Gen-Phon Chen、Yuan-Chuan Lin、Yuh-Meei Lin、Fa-Ching Chen

  DOI：10.1016/s0031-9422(00)81192-9

  日期：1986.7

  Abstract A new anthraquinone, 2,3-dimethoxy-6-methylanthraquinone, has been isolated from Hedyotis diffusa .

  摘要 从白花蛇舌草中分离得到一种新的蒽醌，即2,3-二甲氧基-6-甲基蒽醌。
• Orthobromodiphenylmethane Derivatives as Starting Materials for the Total Synthesis of Anthraquinones
  作者：Wanda P. Almeida、Paulo R.R. Costa

  DOI：10.1080/00397919608003853

  日期：1996.12

  Abstract In this communication we describe the synthesis of four simple anthraquinones by a five-step sequence, using easily available bromobenzaldehydes and phenyllithium derivatives as starting materials.

  摘要 在这篇通讯中，我们描述了通过五步序列合成四种简单的蒽醌，使用容易获得的溴苯甲醛和苯基锂衍生物作为起始材料。
• Applications of [4+2] Anionic Annulation and Carbonyl-Ene Reaction in the Synthesis of Anthraquinones, Tetrahydroanthraquinones, and Pyranonaphthoquinones
  作者：Shyam Basak、Dipakranjan Mal

  DOI：10.1021/acs.joc.7b01987

  日期：2017.10.20

  5-dienoates, susceptible to isomerization by acids and bases, are suitable for the [4+2] anionic annulation to give 3-(2-alkenyl)naphthoates in regiospecific manner. When combined with intramolecular carbonyl-ene reaction (ICE), the accessibility of the naphthoates culminates in a new synthesis of anthraquinones and diastereoselective synthesis of tetrahydroanthraquinones. This strategy has also resulted in a

  易被酸和碱异构化的2,5-二烯六价酸酯适合[4 + 2]阴离子环化反应，以区域特异性方式生成3-（2-烯基）萘甲酸酯。当与分子内羰基-烯反应（ICE）结合使用时，萘甲酸的可及性最终达到新的蒽醌合成和非对映选择性的四氢蒽醌合成。该策略还导致了从3-甲基烯丙基萘甲酸酯的三步合成脱氢herbarin。
• Anthraquinones by Cyclisation of Benzoylbenzoic Acids Produced by the AlCl3-Mediated Friedel--Crafts Reaction of Phthalic Anhydrides with Aromatic Compounds.
  作者：Knut Danielsen、Galya I. Ivanova、Stefan L. Spassov、Jan Sandström、Pál Sohár、Reijo Sillanpää、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0954

  日期：——