N-(anthracen-9-yl)acetamide | 37170-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(anthracen-9-yl)acetamide
• 英文别名: 9-(acetylamino)anthracene；N-[9]anthryl-acetamide；N-[9]Anthryl-acetamid；Anthron-acetylimid；9-acetylaminoanthracene；Monoacetylamino-anthracen；9-Acetamidoanthracene；N-anthracen-9-ylacetamide
• CAS: 37170-96-0
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: MEQRPJCEQSUUTG-UHFFFAOYSA-N

物化性质

• 熔点：
  277 °C (decomp)
• 沸点：
  506.9±19.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(anthracen-9-yl)acetamide 在 Selectfluor 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以97%的产率得到蒽醌
  参考文献：
  名称：

  用Selectfluor™F-TEDA-BF 4在离子液体中氟化活化的芳族体系

  摘要：

  已证明Selectfluor™可溶于离子液体，因此可以高化学选择性和高收率对活化的芳族系统化合物进行“绿色”亲电氟化。

  DOI：

  10.1016/j.jfluchem.2007.11.006
• 作为产物：
  描述：

  9-蒽甲酸 在 硝酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 4.5h， 生成 N-(anthracen-9-yl)acetamide
  参考文献：
  名称：

  Rigaudy, Jean; Ahond, Monique; Barcelo, Jacques, Bulletin de la Societe Chimique de France, 1981, vol. 2, # 5-6, p. 223 - 230

  摘要：

  DOI：

文献信息

• Nitroethane in Polyphosphoric Acid: A New Reagent for Acetamidation and Amination of Aromatic Compounds
  作者：Alexander Aksenov、Nicolai Aksenov、Oleg Nadein、Inna Aksenova

  DOI：10.1055/s-0030-1258767

  日期：2010.10

  A new method of acetamidation of aromatic compounds based on their reaction with nitroethane in polyphosphoric acid has been developed. Upon the hydrolysis of acetamides during the reaction mixture workup, the corresponding amines can be obtained.

  基于芳香族化合物与硝基乙烷在多磷酸中的反应，开发了一种新的芳香族化合物乙酰胺化方法。在反应混合物后处理期间乙酰胺水解后，可以获得相应的胺。
• 1, 2-dihydro-3H-dibenzisoquinoline-1,3-dione anticancer agents
  申请人：Research Corporation Technologies, Inc.

  公开号：US05635506A1

  公开（公告）日：1997-06-03

  This invention relates to a compound useful for the treatment of tumors having the formula: ##STR1##

  这项发明涉及一种用于治疗具有以下化学式的肿瘤的化合物：##STR1##
• Enhanced Nucleophilicity of <i>N</i>-Aryl Amides with peri-CH and Their Condensations with Formaldehyde
  作者：Chunbao Li、Qiang Wang、Xiaoxue Cui、Shasha Liu、Lili Sun

  DOI：10.1055/s-2008-1078485

  日期：——

  N-Aryl amides with peri-CH are capable to condense with formaldehyde to yield N-hydroxymethylated N-aryl amides. The enhanced nucleophilicity is attributed to the single conjugation of the amide nitrogen with the acyl group but not the aryl group. Infrared measurements provide additional evidence for the enhanced nucleophilicity of the amides with peri-CH.

  具有peri-CH 的N-芳基酰胺能够与甲醛缩合以产生N-羟甲基化的N-芳基酰胺。增强的亲核性归因于酰胺氮与酰基而不是芳基的单一共轭。红外测量为具有 peri-CH 的酰胺增强的亲核性提供了额外的证据。
• OXALIC ACID MONOAMIDE LIGAND, AND USES THEREOF IN COUPLING REACTION OF COPPER-CATALYZED ARYL HALOGEN SUBSTITUTE
  申请人：Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

  公开号：EP3326715A1

  公开（公告）日：2018-05-30

  The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C-N, C-O and C-S bonds.

  本发明提供了草酸酰胺配体及其在铜催化的芳基卤化物偶联反应中的用途。具体而言，本发明提供了一种由式 I 代表的化合物的用途，其中各基团的定义在说明书中有所描述。式 I 所代表的化合物可用作铜催化的芳基卤化物偶联反应中的配体，用于形成 C-N、C-O 和 C-S 键。
• Amino-Substituted 2-[2-(Dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-diones. Synthesis, Antitumor Activity, and Quantitative Structure-Activity Relationship
  作者：Salah M. Sami、Robert T. Dorr、Aniko M. Solyom、David S. Alberts、William A. Remers

  DOI：10.1021/jm00006a018

  日期：1995.3

  Sets of 2-[2'-(dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-diones with amino and actylamino groups at each of the eight positions on the anthracene nucleus were synthesized from appropriately substituted anthracenes. Their evaluation in in vitro antitumor and cardiotoxicity assays revealed a very strong dependence of potency on the position of substitution. Certain compounds, including the 4-, 5-, 7-, and 9-amino derivatives, showed significantly higher potency than the unsubstituted parent compound, azonafide. Among them, 7-aminoazonafide had low cardiotoxicity relative to cytotoxicity. In general, the acetylamino analogues were less potent than the amino derivatives against tumor cells and neonatal rat heart myocytes; however, 5-(acetylamino)azonafide was highly cardiotoxic. 9-Aminoazonafide was more efficacious than azonafide or amonafide against P388 leukemia in mice. Statistically significant correlations were made between the ability of amino analogues to increase the transition melt temperature (Delta T-m) of DNA and their potency against solid tumors, leukemia cells, or cardiac myocytes.