1,4-dimethoxy-2-formylanthraquinone | 63965-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-dimethoxy-2-formylanthraquinone
• 英文别名: 1,4-Dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde；1,4-dimethoxy-9,10-dioxoanthracene-2-carbaldehyde
• CAS: 63965-53-7
• 化学式: C₁₇H₁₂O₅
• 分子量: 296.279
• InChiKey: VIYABMBVQYYVKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-dimethoxy-2-formylanthraquinone 在 sodium hydroxide 、 三氯化铝 、 sodium dithionite 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 8-acetyl-6,11-dihydroxy-9,10-dihydro-5,12-naphthacenedione
  参考文献：
  名称：

  Ayyangar, N R; Argade, A B; Mehendale, A R, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 1, p. 3 - 8

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(bromomethyl)-1,4-dimethoxyanthracene-9,10-dione 在 盐酸 、 乌洛托品 作用下， 生成 1,4-dimethoxy-2-formylanthraquinone
  参考文献：
  名称：

  Ayyangar, N R; Argade, A B; Mehendale, A R, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 1, p. 3 - 8

  摘要：

  DOI：

文献信息

• Experiments Directed Towards the Synthesis of Anthracyclinones. XXX. Formation and Use of an Anthraquinone Formyl Ester
  作者：RC Cambie、JBJ Milbank、PS Rutledge

  DOI：10.1071/ch9961203

  日期：——

  Methods for the preparation of methyl 3-formyl-1,4-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-acetate (1) from quinizarin (8) have been investigated. Reaction of the ester (1) with either a titanium enolate of acetone or with acetone trimethylsilyl enol ether and titanium tetrachloride gave the aldol (29) which was then converted into the pentacyclic lactone mixture (41) and (42). While hydrolysis of (41) and (42) with base for long periods (>30 min) gave α,β -unsaturated ketones , brief (2 min) treatment gave the dimethyl ether (5) of the 4-deoxyanthracyclinone (6) corresponding to the antitumour anthracycline 14A10.

  从喹吖啶（8）制备甲基3-甲醛基-1,4-二甲氧基-9,10-二氧-9,10-二氢蒽-2-乙酸酯（1）的方法已经研究。酯（1）与丙酮的钛烯醚盐或与丙酮三甲基硅烯醇醚和四氯化钛反应，生成醛醇（29），然后转化为五环内酯混合物（41）和（42）。将（41）和（42）与碱长时间（＞30分钟）水解得到α，β-不饱和酮，短暂处理（2分钟）得到对应于抗肿瘤蒽喜环素14A10的4-去氧蒽喜环酮（6）的二甲醚（5）。
• Experiments directed towards the synthesis of anthracyclinones. V. Double Claisen rearrangement of 1,4-Bis(allyloxy)anthraquinones
  作者：RC Cambie、H Zhen-Dong、WI Noall、PS Rutledge、PD Woodgate

  DOI：10.1071/ch9810819

  日期：——

  The Claisen rearrangements of 1,4-bis(prop-2'-enyloxy)anthraquinone (4) and 1,4-bis(2'-chloroprop- 2'-enyloxy)anthraquinone (3) in o-dichlorobenzene have been examined. The former gives a low yield of 1,4-dihydroxy-2,3-bis(prop-2'-enyl)anthraquinone (22), and 1,4-dihydroxy-2-(prop-2'-eny1)- anthraquinone (5) as the major product. Also formed is 1-hydroxy-4-propanoyl-2-(prop-2'-enyl)- anthraquinone (6) which arises from an unprecedented rearrangement of one allyloxy group. 1,4-Bis(2?-chloroprop-2'-enyloxy)anthraquinone (3) gives mainly 2-(2'-chloroprop-2'-enyl)-4-(2'- chloroprop-2'-enyloxy)-1-hydroxyanthraquinone (11) and a variety of minor products which are dependent on the time of reaction. Treatment of compound (11) with ethanolic potassium hydroxide, followed by a further Claisen rearrangement, gives a high yield of the synthetically useful 4-(2'-chloro-prop-2'-enyl)-5-hydroxy-2-methyl-6,11-dihydroanthra[1,2-b]furan-6,11-dione (19).

  克莱森重排 1,4-双(丙-2'-烯酰氧基)蒽醌(4)和 1,4-双(2'-氯丙-2'-烯酰氧基)蒽醌(3) 2'-烯酰氧基）蒽醌 (3) 在邻二氯苯中的克莱森重排进行了研究。 进行了研究。前者得到的 1,4-二羟基-2,3-双（丙-2'-烯基）蒽醌 (22)，以及 1,4-二羟基-2-（丙-2'-烯基）-蒽醌（5）为主要产物。同时形成的还有 1-羟基-4-丙酰基-2-(丙-2'-烯基)-蒽醌 (6)。 它是由一个烯丙氧基发生前所未有的重排反应生成的。 1,4-双（2? 2-(2'-氯丙-2'-烯基)-4-(2'-氯丙-2'-烯氧基)-1-羟基蒽醌 (11) 和多种次要产物，这些产物取决于反应时间。 反应时间而定。用乙醇氢氧化钾处理化合物 (11) 再进行一次克莱森重排，可得到高产率的合成有用的 4-(2'-氯)-1-羟基蒽醌 (11)。 useful 4-(2'-chloro-prop-2'-enyl)-5-hydroxy-2-methyl-6,11-dihydroanthra[1,2-b]furan-6,11-dione (19).
• Boniface, Peter J.; Cambie, Richard C.; Carroll, David R., Australian Journal of Chemistry, 1994, vol. 47, # 3, p. 441 - 450
  作者：Boniface, Peter J.、Cambie, Richard C.、Carroll, David R.、Marsh, Nicholas F.、Milbank, Jared B. J.、et al.

  DOI：——

  日期：——
• Ayyangar, N R; Argade, A B; Mehendale, A R, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 1, p. 3 - 8
  作者：Ayyangar, N R、Argade, A B、Mehendale, A R、Deshpande, V H

  DOI：——

  日期：——