1-dimethylaminoanthraquinone | 5960-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-dimethylaminoanthraquinone
• 英文别名: 1-(dimethylamino)anthra-9,10-quinone；N,N-dimethyl-1-aminoanthraquinone；1-dimethylamino-anthraquinone；1-Dimethylamino-anthrachinon；8-dimethylamino anthraquinone；1-(Dimethylamino)anthracene-9,10-dione
• CAS: 5960-55-4
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: FCWBHVZCSYIWHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  1-dimethylaminoanthraquinone 在 硝酸 、 溶剂黄146 作用下， 生成 1-氨基-4-(甲基氨基)蒽醌
  参考文献：
  名称：

  DE156759

  摘要：

  公开号：
• 作为产物：
  描述：

  1-氯蒽醌 、 二甲胺 以 乙醇 为溶剂， 生成 1-dimethylaminoanthraquinone
  参考文献：
  名称：

  二甲基亚砜中氢氧化钾存在下氨基蒽醌的酰胺离子形成和N-烷基化

  摘要：

  在二甲基亚砜 (DMSO) 中，在粉末氢氧化钾的存在下，通过氨基-和（单烷基氨基）蒽醌的氨基去质子化形成酰胺离子。在氮气氛下，这些酰胺离子转变为它们的自由基阴离子。1-氨基蒽醌的酰胺离子与过量的烷基卤反应生成1-烷基氨基蒽醌，而2-氨基蒽醌的N-烷基化以良好的产率得到2-二烷基氨基蒽醌。2-氨基二苯甲酮经历单-N-烷基化，而4-氨基偶氮苯和对硝基苯胺经历二-N-烷基化。还发现 DMSO 的碳负离子很容易攻击（二烷基氨基）蒽醌的羰基。

  DOI：

  10.1246/bcsj.58.1458

文献信息

• Perfluoroalkylquinones. Synthesis Using Bis(perfluoroalkanoyl) Peroxides, Absorption Bands, and Solubility
  作者：Masaki Matsui、Shigeru Kondoh、Katsuyoshi Shibata、Hiroshige Muramatsu

  DOI：10.1246/bcsj.68.1042

  日期：1995.3

  The reactions of 1,4-benzo-, naphtho-, and 9,10-anthraquinones with bis(perfluoroalkanoyl) peroxides gave the corresponding perfluoroalkylated derivatives. Those of 2-methyl- and 2-[4-(chloroanilino)]-1,4-naphthoquinones with bis(oxaperfluoroalkanoyl) peroxides afforded the dichloromethyl and trifluoromethyl derivatives, respectively. Absorption bands of the perfluoroalkylated naphtho- and anthraquinone dyes showed a slight hypsochromic shift. The solubilities of the perfluoroalkylated anthraquinone dyes into hexane were much more higher than those of the non-perfluoroalkylated ones.

  1,4-苯并蒽醌、萘并蒽醌和 9,10-蒽醌与双（全氟烷酰基）过氧化物的反应生成了相应的全氟烷基化衍生物。2-甲基和 2-[4-(氯苯胺基)]-1,4-萘醌与双(氧代全氟烷酰基)过氧化物的反应分别产生了二氯甲基和三氟甲基衍生物。全氟烷基化萘醌和蒽醌染料的吸收带显示出轻微的低色移。全氟烷基化蒽醌染料在正己烷中的溶解度远高于非全氟烷基化蒽醌染料。
• Photochemical substitution of amino- and hydroxy-anthraquinones
  作者：Kenneth Hamilton、John A. Hunter、Peter N. Preston、John O. Morley

  DOI：10.1039/p29800001544

  日期：——

  only, while 2-aminoanthraquinone gives the sodium 3-sulphonate. In contrast, 1-hydroxyanthraquinone gives a mixture of the sodium 2- and 4-sulphonates and disodium 2,4-disulphonates. The different substitution pattern observed for 1-amino- and 1-hydroxy-anthraquinone has been rationalised by application of semi-empirical molecular orbital theory.

  在50％吡啶水溶液中有过量的亚硫酸钠或硫化物存在下，用可见光照射1-氨基蒽醌，分别得到1-氨基蒽醌-2-磺酸钠和-2-硫醇钠，收率很好。在与亚硫酸钠相似的条件下，1-甲基氨基-，1-氨基-4-氯-和1-氨基-5-氯-蒽醌仅给出各自的2-磺酸钠，而2-氨基蒽醌得到3-磺酸钠。 。相反，1-羟基蒽醌得到2-和4-磺酸钠和2，4-二磺酸二钠的混合物。通过应用半经验分子轨道理论已经合理化了对1-氨基和1-羟基蒽醌的不同取代方式。
• Anormalous Halogen to Dimethylamino Replacement with<i>N</i>,<i>N</i>-Dimethylformamide Catalyzed by Ethylenediamine or 2-Aminoethanol
  作者：Hiroshi Yamamoto

  DOI：10.1246/bcsj.55.2685

  日期：1982.8

  2-chloroanthraquinone and 2-amino-4-chloro-6-hydroxypyrimidine exclusively gave the dimethylamino derivatives upon heating in DMF at 90 °C in the presence of ethylenediamine or ethanolamine. A possible reaction pathway for this unusual exchange reaction was discussed.

  1- 和 2- 氯蒽醌和 2-氨基-4-氯-6-羟基嘧啶在乙二胺或乙醇胺的存在下，在 DMF 中于 90 °C 加热时仅得到二甲氨基衍生物。讨论了这种不寻常的交换反应的可能反应途径。
• Process for the manufacture of N-alkylamino- and
  申请人：Ciba-Geigy Corporation

  公开号：US04044030A1

  公开（公告）日：1977-08-23

  A process for the manufacture of N-alkylamino- and N,N-dialkylaminoanthraquinone from the corresponding nitroanthraquinones, which comprises reacting substituted or unsubstituted nitroanthraquinones or dinitroanthraquinones with at least twice the molar amount, referred to the nitro groups to be reacted, of an alkyl acid amide, at temperatures between 100.degree. C and the boiling point of the alkyl acid amide. The present invention provides a process for the manufacture of N-alkylamino- and N,N-dialkylaminoanthraquinones from the corresponding nitroanthraquinones, which process comprises reacting substituted or unsubstitued nitroanthraquinones or dinitroanthraquinones with at least twice the molar amount, referred to the nitro groups to be reacted, of an alkyl acid amide which is simultaneously reactant and reaction medium, at temperatures between 100.degree. C and the boiling point of the alkyl acid amide. The reaction takes place according to the general reaction equation ##STR1## wherein R and R', which are the same or different, represent alkyl, aralkyl, cycloalkyl or hydroxyalkyl radicals of 1 to 8 carbon atoms, n is 0 or 1, X represents a functional substituent, for example the carboxyl, sulpho, hydroxy, amino or halogen group, which can be attached direct or through a bridge member to the anthraquinone nucleus. The reaction can be carried out with mononitroanthraquinones and/or dinitroanthraquinones. The aminoanthraquinones obtained by the process of this invention are known and are useful dyes or dyestuff intermediates. The aminolysis of nitroanthraquinones is described in German Pat. Nos. 136.777, 136.778 and 144.634. However, polar solvents, such as water, alcohols or pyridine, are used as reaction media therein. The use of polar solvents as reaction media results in only very poor yields and lengthy reaction times are required. For example, the reaction of 1-nitroanthraquinone with a 300% excess of isopropylamine at 75.degree. C after 100 hours gives a yield of only 70% of 1-isopropylaminoanthraquinone. Swiss Pat. application No. 12793/74 describes the aminolysis by reacting nitroanthraquinones with organic amines using dipolar aprotic solvents which contain --SO.sub.2 or --SO groups as reaction media. This process is satisfactory up to the recovery of the solvents used as reaction medium, which may have to be separated by distillation from the amines used as reactants. By comparison, N-alkylamino- and N,N-dialkylamino-anthraquinones are obtained surprisingly in very high and often even quantitative yields by the process of this invention. The products are obtained in a high degree of purity, so that mostly they do not need to be purified any more. The reaction conditions are simple and the reaction course is easily kept under control. No problems regarding corrosion or of a technical nature arise in respect of the apparatus used and the recovery of the excess acid amide used as reaction medium presents no difficulties. The reaction course is uniform and virtually no residues occur, so that the process of this invention also marks a considerable advance especially from the ecological standpoint. The excess acid amide can be almost completely recovered after the reaction by simple distillation or by filtering it off from the product, and reused for a fresh batch. Examples of aminoanthraquinones which can be obtained by the process of this invention are: 1-isopropylaminoanthraquinone, 1-isobutylamino-2-methylanthraquinone, 1-methylaminoanthraquinone, 1-diethylaminoanthraquinone, 1-cyclohexylaminoanthraquinone, the sodium salt of 1-isopropylaminoanthraquinone-6/7-sulphonic acid, 1-isobutylaminoanthraquinone, 1-diisopropyl-, 1-diisobutyl- and 1-dicyclohexylaminoanthraquinone, 1-isopropylamino-2-methylanthraquinone 1-cyclohexylamino-2-methylanthraquinone, 1,5-bis-methylaminoanthraquinone and 1-dimethylaminoanthraquinone. The aminolysis is carried out in conventional reaction vessels or autoclaves. A suitable apparatus is the rotary evaporator or, for batches produced on an industrial scale, the paddle drier (Venulett). The reaction temperature will be at least 100.degree. C. The preferred reaction temperature is between 160.degree. and 200.degree. C. The aminolysis can be carried out both under pressure and without pressure. It is preferred to operate without pressure. The reaction time is from 0.5 to 15 hours, preferably 1 to 5 hours. The weight ratio of the acid amide as reactant and reaction medium to the nitroanthraquinone is advantageously between 4:1 to 10:1. Suitable acid amides are those of the formulae HCONHR, RCONHR, HCONRR', RCONNRR' or those of the formulae PO(--NRR').sub.3, SO.sub.2 (--NRR').sub.2 or SO(--NRR').sub.2, wherein R and R', which are the same or different, represent alkyl, aralkyl, cycloalkyl or hydroxyalkyl radicals of 1 to 8 carbon atoms. An alkyl group represented by each of R and R' can be the same or different, straight-chain or branched, and is in particular a low molecular alkyl group of 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, tert.butyl, or a long-chain alkyl group, such as hexyl or octyl. A cycloalkyl group represented by each of R and R' is in particular the cyclohexyl group and an aralkyl group represented by R and R' is above all the benzyl or phenethyl group. Preferably each of R and R' represents a lower alkyl group. Examples of acid amides which can be used according to the invention are: N-methyl formamide, N-methyl acetamide, N,N-dimethyl formamide, N-ethyl formamide and hexamethylphosphoric triamide or tetramethyl thionyl diamide. The reaction is carried out, for example, in such a way that the reactants, nitroanthraquinone and acid amide, are charged into a reaction vessel and stirred for several hours at temperatures between 100.degree. and 200.degree. C. When the reaction is complete, the excess acid amide is distilled off and can be reused. In many cases the product crystallises out after the reaction mixture has cooled, so that it is separated by filtration, and the mother liquor (i.e., excess acid amide with a small amount of dissolved product) can be reused for further reactions. It will be readily understood that the products can also be isolated by diluting the reaction mixture with water or alcohols and subsequent filtration. The following Examples illustrate the process of the present invention without implying any restriction to what is described therein. The parts are by weight.

  一种从相应的硝基蒽醌制备N-烷基氨基和N，N-二烷基氨基蒽醌的工艺，包括将取代或未取代的硝基蒽醌或二硝基蒽醌与至少是硝基反应物摩尔量的两倍的烷基酸酰胺反应，在100°C至烷基酸酰胺沸点之间的温度下进行。本发明提供了一种从相应的硝基蒽醌制备N-烷基氨基和N，N-二烷基氨基蒽醌的工艺，该工艺包括将取代或未取代的硝基蒽醌或二硝基蒽醌与至少是硝基反应物摩尔量的两倍的烷基酸酰胺同时作为反应物和反应介质反应，在100°C至烷基酸酰胺沸点之间的温度下进行。反应按照一般的反应方程式进行，其中R和R'代表1至8个碳原子的烷基、芳基烷基、环烷基或羟基烷基基团，n为0或1，X代表一个官能基取代物，例如羧基、磺酸基、羟基、氨基或卤素基，可以直接或通过桥接成员连接到蒽醌核上。反应可以使用单硝基蒽醌和/或二硝基蒽醌进行。本发明所得到的氨基蒽醌是已知的，是有用的染料或染料中间体。本发明的氨解反应在德国专利号136.777、136.778和144.634中有所描述。然而，在其中使用极性溶剂，如水、醇或吡啶，作为反应介质。使用极性溶剂作为反应介质会导致产率非常低，需要较长的反应时间。例如，在75°C下，1-硝基蒽醌与300%过量的异丙胺反应100小时后，仅得到70%的1-异丙基氨基蒽醌收率。瑞士专利申请号12793/74描述了通过使用含有--SO2或--SO基团的双极非质子溶剂作为反应介质，将硝基蒽醌与有机胺反应的氨解反应。该工艺在回收用作反应介质的溶剂方面是令人满意的，可能需要通过蒸馏从作为反应物的胺中分离出来。相比之下，本发明的工艺出乎意料地以非常高甚至定量的收率获得N-烷基氨基和N，N-二烷基氨基蒽醌。产品的纯度很高，因此大多数情况下它们不需要再经过纯化。反应条件简单，反应过程容易控制。在所使用的设备和回收过量的作为反应介质的酸酰胺方面没有腐蚀或技术性问题。反应过程是均匀的，几乎不会产生残留物，因此从生态角度来看，本发明的工艺也是一个重大的进步。反应后，可以通过简单的蒸馏或从产物中过滤掉过量的酸酰胺，几乎完全地回收过量的酸酰胺，并用于新的批次。可以在常规反应器或高压釜中进行氨解反应。适当的设备是旋转蒸发器或用于工业规模批次生产的搅拌干燥器（Venulett）。反应温度将至少为100°C。优选反应温度在160°C至200°C之间。氨解反应可以在有压力和无压力下进行。最好不使用压力。反应时间为0.5至15小时，优选为1至5小时。作为反应物和反应介质的酸酰胺与硝基蒽醌的重量比有利地为4:1至10:1。适用的酸酰胺是HCONHR，RCONHR，HCONRR'，RCONNRR'的公式，或PO（-NRR'）3，SO2（-NRR'）2或SO（-NRR'）2的公式，其中R和R'相同或不同，代表1至8个碳原子的烷基、芳基烷基、环烷基或羟基烷基基团。由每个R和R'代表的烷基组可以相同或不同，直链或支链，并且特别是1至4个碳原子的低分子烷基组，如甲基、乙基、丙基、异丙基、叔丁基，或长链烷基组，如己基或辛基。由每个R和R'代表的环烷基组特别是环己基组，由R和R'代表的芳基烷基组主要是苄基或苯乙基组。最好每个R和R'都代表较低的烷基组。可以使用的酸酰胺的例子是N-甲基甲酰胺、N-甲基乙酰胺、N，N-二甲基甲酰胺、N-乙基甲酰胺和六甲基磷酸三酰胺或四甲基硫酰二胺。例如，反应可以这样进行，即将反应物硝基蒽醌和酸酰胺加入反应器中，在100°C至200°C的温度下搅拌数小时。当反应完成后，过量的酸酰胺被蒸馏掉，并可以被再次使用。在许多情况下，产物在反应混合物冷却后结晶出来，因此通过过滤分离，母液（即带有少量溶解的产物的过量酸酰胺）可以再次用于进一步的反应。很容易理解，也可以通过将反应混合物稀释水或醇并随后过滤来分离产物。以下实例说明本发明的工艺，但不意味着对所描述的内容有任何限制。
• Antiviral Compounds and Methods of Use Thereof
  申请人：Guenther Richard H.

  公开号：US20130071353A1

  公开（公告）日：2013-03-21

  Inhibitors of retroviral propagation, methods of treatment and prevention of retroviral infections using the inhibitors, and pharmaceutical compositions including the inhibitors, are disclosed.

  本文披露了逆转录病毒传播的抑制剂、使用这些抑制剂进行逆转录病毒感染的治疗和预防方法，以及包括这些抑制剂的制药组合物。