10-(methoxyimino)phenanthren-9-one | 89968-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 10-(methoxyimino)phenanthren-9-one
• 英文别名: phenanthrene-9,10-dione-mono-(O-methyl oxime )；Phenanthren-9,10-dion-mono-(O-methyl-oxim)；10-methoxyiminophenanthren-9-one
• CAS: 89968-51-4
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: CHCDOMUGICKGGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-(methoxyimino)phenanthren-9-one 在 氯化亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 甲苯 、 苯 为溶剂， 反应 222.5h， 生成 N⁴,N⁵-bis(3-morpholinopropyl)-7-oxo-7H-dibenzo[de,g]quinoline-4,5-dicarboxamide
  参考文献：
  名称：

  Design, synthesis and anticancer activity of oxoaporphine alkaloid derivatives

  摘要：

  A series of new oxoaporphine derivatives were synthesized and their inhibitory activity of topoisomerase I, cytotoxicity and DNA-binding properties were studied. Oxoaporphine can strongly inhibit topoisomerase I at concentrations of 5-50 µM and the cytotoxicity of the derivatives are more potent than their lead compound. Hypochromism, broadening and red shift in the absorption spectra were observed when these compounds bind to calf thymus DNA (CT DNA). These spectral characteristics were consistent with the intercalative binding of these compounds.

  DOI：

  10.3109/14756366.2013.845818
• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 菲醌 生成 10-(methoxyimino)phenanthren-9-one
  参考文献：
  名称：

  Epsztein, Memorial des services chimiques de l'Etat, 1951, vol. 36, p. 353,370

  摘要：

  DOI：
• 作为试剂：
  描述：

  氧杂蒽 在 10-(methoxyimino)phenanthren-9-one 作用下， 反应 0.17h， 以57%的产率得到占吨酮
  参考文献：
  名称：

  的反应ø -甲基ö -quinone monoximes用甲基，亚甲基和取代的methine-芳族化合物。苯并[ d ]恶唑和1,4-苯并恶嗪衍生物的合成

  摘要：

  ø -甲基ø -quinone肟1发生反应热用化合物2A-d或6A，6B或图7A，B主要得到相应的2-取代的phenanthroxazoles 3A-C和8。1与芳族亚甲基化合物10a-c的反应以中等至高收率得到酮13a-c。从一恶魔15a，b与一些上述反应物的反应中也获得了类似的产物。的意想不到的产品5和20从反应得到的1与2-甲基咪唑（2D）和苯基环氧乙烷（19），而4 H -1,4-恶嗪衍生物23是由1与茚（21）的反应获得的。

  DOI：

  10.1002/jhet.5570340602

文献信息

• Synthesis, biological evaluation and molecular modeling of oxoisoaporphine and oxoaporphine derivatives as new dual inhibitors of acetylcholinesterase/butyrylcholinesterase
  作者：Huang Tang、Yong-Biao Wei、Chi Zhang、Fang-Xian Ning、Wei Qiao、Shi-Liang Huang、Lin Ma、Zhi-Shu Huang、Lian-Quan Gu

  DOI：10.1016/j.ejmech.2009.01.021

  日期：2009.6

  synthesized as acetylcholinesterase (AChE) and/or butyrylcholinesterase (BuChE) inhibitors. The AChE inhibition potency of synthetic oxoaporphine derivatives was decreased about 2–3 orders of magnitude as compared with that of oxoisoaporphine derivatives. Non-competitive binding mode was found for both kinds of derivatives. Molecular docking simulations on the oxoisoaporphine derivatives 7 series and

  从中草药中分离出的Aporphine生物碱是重要的天然产物。我们最近报道说，氧代异aphophine生物碱的合成衍生物比BuChE表现出较高的乙酰胆碱酯酶抑制活性和对AChE的高选择性（Bioorg。Med。Chem。Lett。2007，17，3765-3768）。本文提出了进一步的研究结果。一系列新的氧杂卟啉生物碱衍生物（5a - j，4-羧酸酰胺-7-氧代-7 H-二苯并[ de，g ]喹啉，Ar-CONH（CH 2）n NR）及其季me盐（6a – h，Ar-CONH（CH 2）n N+（CH 3）RI -设计和为乙酰胆碱酯酶和/或丁酰胆碱酯酶（BuChE的）抑制剂合成）。合成的氧磷卟啉衍生物的AChE抑制能力与氧代异吗啡衍生物相比降低了约2-3个数量级。两种衍生物都发现了非竞争性结合模式。氧代异aporphine衍生物7系列和oxoaporphine衍生物6系列与来自加州鱼雷的AC
• Reactions of 2-(methoxyimino)benzen-1-ones with α-alkylethoxycarbonylmethylene(triphenyl)phosphoranes
  作者：Demetrios N Nicolaides、Daman R Gautam、Konstantinos E Litinas、Christos Manouras、Konstantina C Fylaktakidou

  DOI：10.1016/s0040-4020(01)00942-5

  日期：2001.11

  The title 2-(methoxyimino)benzen-1-ones react with α-alkylethoxycarbonylmethylene(triphenyl)phosphoranes to give 2H-[b][1,4]benzoxazine derivatives along with benzoxazole and indole derivatives. Reaction mechanisms to explain the formation of products obtained are suggested.

  标题2-（甲氧基亚氨基）苯并-1-酮与α-烷基乙氧基羰基亚甲基（三苯基）正膦反应，得到2 H- [ b ] [1,4]苯并恶嗪衍生物以及苯并恶唑和吲哚衍生物。建议了反应机理以解释所得产物的形成。
• Synthesis of 1-methoxy-1H-phenanthro[9,10-c][1,2]oxazine and its transformation to triphenylene-o-dicarboxylic derivatives
  作者：Demetrios N. Nicolaides、Raed Wajih Awad、Georgios K. Papageorgiou、Julia Stephanidou-Stephanatou、Aristides Terzis、Catherine P. Raptopoulou

  DOI：10.1016/0040-4039(95)02314-3

  日期：1996.2

  1-Methoxy-1H-phenanthro[9,10-c][1,2]oxazine 4 prepared from teh reaction of 10-(methoxyimino)phenanthren-9-one 1 with benzoylmethylene(triphenyl)phosphorane 2, reacts thermally with dienophiles 6, 9a, b to give the triphenylene-o-dicarboxylic derivatives 8, 11a,b in high yield.

  1-甲氧基-1H-菲并[9,10-c] [1,2]恶嗪4由10-（甲氧基亚氨基）菲-9-酮1与苯甲酰基亚甲基（三苯基）膦2的反应制得，并与亲二烯体6热反应，9a，b以高收率得到三亚苯基-邻-二羧酸衍生物8，11a，b。
• Synthesis of phenanthro[9, 10-d]oxazoles from 10-(methoxyimino)phenanthrene-9-one
  作者：Demetrios N. Nicolaides、Evangelia A. Varella、R. Wajih Awad

  DOI：10.1016/s0040-4020(01)87251-3

  日期：1993.8

  10-(Methoxyimino)phenanthren-9-one 3 easily reacts with the methyl substituted aromatics 4(a-d), as well as with alpha-bromo-p-xylene 6 and the alpha-substituted methyl derivatives 7(a-i), to afford in 5-64% yield the corresponding 2-aryl substituted phenanthro[9,10-d]oxazoles 5(a-g), most probably via a free radical reaction sequence. In several cases the unsubstituted oxazole 12 is also obtained, while reaction of compound 3 with the N-methyl substituted amines 7g and 14(ab) leads to the aminooxazoles 13 and 15(a,b) respectively.
• Synthesis of some fused pyridine-and oxazole-polycyclic systems from 10-(methoxyimino)phenanthren-9-one
  作者：D.N. Nlcolaides★、G.K. Papageorgiou、J. Stephanidou-Stephanatou

  DOI：10.1016/s0040-4020(01)89093-1

  日期：——