1-氨基-8-氯蒽-9,10-二酮 | 117-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-氨基-8-氯蒽-9,10-二酮
• 英文名称: 1-amino-8-chloro-9,10-anthraquinone
• 英文别名: 1-amino-8-chloroanthraquinone；8-chloro-1-aminoanthraquinone；1-amino-8-chloro-anthraquinone；1-Amino-8-chlor-anthrachinon；1-amino-8-chloro-9,10-anthracenedione；1-Amino-8-chloranthrachinon；1-amino-8-chloroanthracene-9,10-dione
• CAS: 117-09-9
• 化学式: C₁₄H₈ClNO₂
• 分子量: 257.676
• InChiKey: JMNNJCADZZBEOW-UHFFFAOYSA-N

物化性质

• 熔点：
  227-228 °C
• 沸点：
  500.9±50.0 °C(Predicted)
• 密度：
  1.486±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-氨基-8-氯蒽-9,10-二酮 在 ammonium hydroxide 、 三氟化硼 、 锌 作用下， 以 邻二氯苯 为溶剂， 生成 1-Chlor-8-fluoranthracen
  参考文献：
  名称：

  Dissociation constants of 8-substituted 9,10-ethanoanthracene-1-carboxylic acids and related compounds. Evidence for the field model for the polar effect

  摘要：

  DOI：

  10.1021/ja00764a032
• 作为产物：
  描述：

  1-氯-8-硝基蒽-9,10-二酮 在 sodium sulfide 作用下， 反应 1.0h， 以88%的产率得到1-氨基-8-氯蒽-9,10-二酮
  参考文献：
  名称：

  7-氧代-7H-二苯并[f，ij]异喹啉和7-氧代-7H-苯并[e]亚氨基吡啶衍生物的合成及细胞毒活性。

  摘要：

  从氨基蒽醌制备了一系列带有阳离子侧链的7-氧代-7H-二苯并[f，ij]异喹啉和7-氧代-7H-苯并[e]亚氨基。通过与尿素或二甲基乙酰胺的初始缩合，由1-氨基蒽醌制备过亚im啶。由氨基蒽醌羧酸制备了二苯并异喹啉的一系列2-，4-，8-和11-羧基衍生物。由这些经由酰胺，胺或亚甲基接头制备阳离子衍生物，以研究侧链定位对生物活性的影响。在一系列与羧酰胺连接的化合物中，增加的细胞毒性顺序为8-<4- <2- <11-。2-和4-羧酰胺对小鼠体内的皮下结肠38肿瘤表现出明显的生长延迟，

  DOI：

  10.1021/jm010041l

文献信息

• Process for the preparation of 1-acylamino-5(8)-chloroanthraquinones
  申请人：Bayer Aktiengesellschaft

  公开号：US04179450A1

  公开（公告）日：1979-12-18

  The invention relates to a novel process for the preparation of 1-acylamino-5(8)-chloroanthraquinones, which are starting materials for the preparation of vat dyes. It is characterized in that 1,5(8)-dichloroanthraquinones is reacted with ammonia at temperatures of 190.degree. to 240.degree. C., the amino groups in the reaction mixture are completely acylated and the more sparingly soluble diacylaminoanthraquinone is separated off from the more readily soluble monoacylaminochloroanthraquinone. The new process yields reaction products which are purer and cheaper than those which are obtained by conventional methods. Moreover there are smaller waste water problems.

  该发明涉及一种制备1-酰氨基-5(8)-氯蒽醌的新工艺，这些是制备缸染料的起始原料。其特点在于1,5(8)-二氯蒽醌与氨在温度为190到240摄氏度下反应，反应混合物中的氨基完全酰化，并将不溶性较小的二酰氨基蒽醌与较易溶解的单酰氨基氯蒽醌分离。这一新工艺产生的反应产物比传统方法得到的更纯净、更便宜。此外，废水问题也更小。
• A Facile Method for Preparing Substituted 1-Aminoanthraquinones
  作者：Henry C. Wormser、Manik S. Sardessai、Hanley N. Abramson

  DOI：10.1080/00397919308011182

  日期：1993.12

  Abstract An efficient and simple preparation of α - substituted aminoanthraquinones using 2,2-dialkoxyethylamines is described.

  摘要 描述了使用 2,2-二烷氧基乙胺有效且简单地制备 α - 取代的氨基蒽醌。
• Photoisomerization of Bis(tridentate) 2,6-Bis(1<i>H</i> -pyrazol-1-yl)pyridine Ligands Exhibiting a Multi-anthracene Skeleton
  作者：Ivan Šalitroš、Olaf Fuhr、Miroslav Gál、Michal Valášek、Mario Ruben

  DOI：10.1002/chem.201700825

  日期：2017.7.26

  of 2,6‐bis(1H‐pyrazol‐1‐yl)pyridine are linked through multi‐1,8‐diethynylanthracene moieties. The optimized synthesis of the three isostructural analogues 1 a, 1 b, and 1 c, containing the anthraquinone, anthracene, and 10‐methoxyanthracene units, respectively, is reported. The resulting spatial face‐to‐face arrangement of the peripheral anthracene rings enables to trigger the intramolecular [4+4]

  描述了一种新颖的分子设计，其中通过2,6-双（1 H-吡唑-1-基）吡啶制成的两个外围部分通过多1,8-二乙炔基蒽类部分相连。报道了分别包含蒽醌，蒽和10-甲氧基蒽单元的三个同构类似物1a，1b和1c的优化合成。外围蒽环的所得空间面-面结构，可以触发的分子内[4 + 4]光环加成，得到异构体P1 b和P1Ç，其可以是热裂解回到原来的蒽衍生物1b中和1c中， 分别。X射线单晶衍射研究证实了化合物1 a – 1 c及其相应的异构体P1 b和P1 c的预期分子结构。研究和讨论了所有合成化合物的光谱，光学和电化学性质。
• Process for the manufacture of aminoanthraquinones
  申请人：Ciba-Geigy AG

  公开号：US04021456A1

  公开（公告）日：1977-05-03

  A process for the manufacture of 1-aminoanthraquinone and derivatives thereof and of diaminoanthraquinones by reduction of 1-nitroanthraquinone and the corresponding derivatives thereof and dinitroanthraquinone, which process comprises the use of a hydronaphthalene as reducing agent and solvent.

  一种制造1-氨基蒽醌及其衍生物和二氨基蒽醌的方法，包括将1-硝基蒽醌及其对应的衍生物和二硝基蒽醌还原，所使用的还原剂和溶剂为氢化萘。
• [EN] ANTI-TUMOUR COMPOUNDS<br/>[FR] COMPOSES ANTITUMORAUX
  申请人：UNIV TROBE

  公开号：WO2002030906A1

  公开（公告）日：2002-04-18

  A compound of formula (II) in which positional numbering, where mentioned, refers to the system illustrated above, and one or more W and one or more U are attached to a ring carbon or carbons at any of positions 1-11 or to a ring nitrogen at position 7 if present, and in which: W is C(=Q)NRCHJ(CH2)nR1 where Q is O or S, R is hydrogen or a C¿1-4? alkyl group which is optionally substituted with one or more OH or NH2 groups, J is H or a C1-C6 alkyl group optionally substituted with OH, OMe, NH2, NHMe or NMe2 functions, R?1¿ is C(=NR2)NH2, NHC(=NR3)NH2 or NR4R5, where each of R?2 and R3¿ are independently hydrogen or a C¿1-4? alkyl group which is optionally substituted with one or more OH or NH2 groups, and R?4 and R5¿ are independently hydrogen or a C¿1-4? alkyl group which is optionally substituted with one or more OH or NH2 groups, or R?4 and R5¿ together with the nitrogen atom to which they are attached form an optionally substituted saturated or unsaturated heterocyclic group; and n is an integer from 0 to 5; X, Y, V are independently CH or N; Z is CH¿2?, CH-C1-4 alkyl, CO, O, S, SO, SO2, N-C1-4 alkyl or NH; and U is H, halo, OH, CO2H, NR?6R7¿, nitro, cyano, C¿1-6? alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 aminoalkyl or C1-6 aminoalkoxy in which R?6 and R7¿ have the same definitions as R?4 and R5¿ above; or a pharmaceutically-acceptable salt, N-oxide, hydrate, solvate, pharmaceutically acceptable derivative, pro-drug, tautomer or isomer thereof, with the proviso that W at position 4 cannot be CONH(CH¿2?)2NMe2, CONH(CH2)2NEt2, CONH(CH2)3NMe2, CONH(CH2)3NEt2, CONH(CH2)2Npiperidyl, or CONH(CH2)2Nmorpholinyl, when X and Y are N, V is CH, U is H and Z is CO. 'Bis' compounds and carboxylic acid precursors are also claimed. The compounds are useful in the treatment of neoplastic conditions such as cancer.

  式（II）的化合物，其中位置编号（如有提及）是指上述系统，其中一个或多个W和一个或多个U附加到任何1-11位置的环碳或碳上，或附加到7号位置的环氮（如存在），其中：W是C（=Q）NRCHJ（CH2）nR1，其中Q为O或S，R为氢或可选地取代一个或多个OH或NH2基团的C¿1-4？烷基，J为H或可选地取代OH，OMe，NH2，NHMe或NMe2功能的C1-C6烷基，R?1¿为C（=NR2）NH2，NHC（=NR3）NH2或NR4R5，其中R?2和R3¿各自独立地为氢或可选地取代一个或多个OH或NH2基团的C¿1-4？烷基，而R?4和R5¿独立地为氢或可选地取代一个或多个OH或NH2基团的C¿1-4？烷基，或者R?4和R5¿与它们附着的氮原子一起形成可选地取代的饱和或不饱和杂环基团；n是0到5的整数；X，Y，V各自独立地为CH或N；Z为CH¿2？，CH-C1-4烷基，CO，O，S，SO，SO2，N-C1-4烷基或NH；U为H，卤素，OH，CO2H，NR?6R7¿，硝基，氰基，C¿1-6？烷基，C1-6卤代烷基，C1-6烷氧基，C1-6卤代烷氧基，C1-6氨基烷基或C1-6氨基烷氧基，其中R?6和R7¿与上述R?4和R5¿的定义相同；或其药学上可接受的盐，N-氧化物，水合物，药学上可接受的衍生物，前药，互变异构体，但在X和Y为N，V为CH，U为H，Z为CO时，位置4的W不能是CONH（CH¿2？）2NMe2，CONH（CH2）2NEt2，CONH（CH2）3NMe2，CONH（CH2）3NEt2，CONH（CH2）2Npiperidyl或CONH（CH2）2Nmorpholinyl。还声明了“双”化合物和羧酸前体。这些化合物在治疗癌症等肿瘤条件方面有用。

表征谱图