2-phenyl-3-(n-propylamino )naphthalene-1,4-dione | 1380443-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-phenyl-3-(n-propylamino )naphthalene-1,4-dione
• 英文别名: 2-phenyl-3-(propylamino)naphthalene-1,4-dione
• CAS: 1380443-71-9
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: ZCZOWDOKVRIMHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二甲基-乙烯基磷酸酯 、 2-phenyl-3-(n-propylamino )naphthalene-1,4-dione 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 以61%的产率得到(E)-dimethyl 2-(5,8-dioxo-7-phenyl-6-(propylamino)-5,8-dihydronaphthalen-1-yl)vinyl phosphonate
  参考文献：
  名称：

  Substituent-Enabled Oxidative Dehydrogenative Cross-Coupling of 1,4-Naphthoquinones with Alkenes

  摘要：

  A Rh-catalyzed oxidative dehydrogenative cross-coupling of 1,4-naphthquinones with alkenes was achieved by using a substituent-enabled C(sp(2))-H functionalization (SEF) strategy. The method shows high functional group tolerance, broad substrate scope, and great potential for further functional transformations.

  DOI：

  10.1021/jo501419s
• 作为产物：
  描述：

  2-溴-1,4-萘醌 在 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-phenyl-3-(n-propylamino )naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis, reactive oxygen species generation and copper-mediated nuclease activity profiles of 2-aryl-3-amino-1,4-naphthoquinones

  摘要：

  Here we report a series of 2-aryl-3-amino-1,4-naphthoquinones that generated reactive oxygen species (ROS) such as superoxide and hydrogen peroxide upon incubation in pH 7.4 under ambient aerobic conditions. ROS generation from these compounds was sensitive to structural modifications at the 3-amino position and a 2-aryl substituent promoted ROS generation. A number of these compounds were found to induce DNA damage in the presence of Cu(II) without any added reducing agent. Our data suggests that 2-aryl-3-amino-1,4-naphthoquinones' propensity to produce ROS correlated well with its DNA damage inducing ability. 2-Phenyl-3-pyrrolid-1-yl-1,4-naphthoquinone (22) was found to damage DNA at 1 mu M suggesting that these compounds may have therapeutic relevance in targeting cancers which over-express Cu(II) (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.009

文献信息

• Naphthoquinone-Directed C–H Annulation and C_sp³–H Bond Cleavage: One-Pot Synthesis of Tetracyclic Naphthoxazoles
  作者：Meining Wang、Chi Zhang、Li-Ping Sun、Chunyong Ding、Ao Zhang

  DOI：10.1021/jo500572u

  日期：2014.5.16

  One-pot synthesis of tetracyclic naphthoxazole derivatives from electron-deficient naphthoquinones and alkynes was achieved via Rh(III)-catalyzed C–H activation and Csp3–H bond cleavage for the first time. This approach proceeds through a tandem cascade process involving substrate tautomerization, C–H activation, oxidative addition, cyclization, and aromatization. In addition, broad substrate scope

  首次通过Rh（III）催化的C–H活化和C sp 3 –H键裂解，从缺电子的萘醌和炔烃一锅合成四环萘恶唑衍生物。这种方法通过串联级联过程进行，涉及底物互变异构，CH活化，氧化加成，环化和芳构化。另外，广泛的底物范围，简单的起始原料和空间耐受性使得该策略具有很大的实用性。
• Synthesis, reactive oxygen species generation and copper-mediated nuclease activity profiles of 2-aryl-3-amino-1,4-naphthoquinones
  作者：Vinayak S. Khodade、Allimuthu T. Dharmaraja、Harinath Chakrapani

  DOI：10.1016/j.bmcl.2012.04.009

  日期：2012.6

  Here we report a series of 2-aryl-3-amino-1,4-naphthoquinones that generated reactive oxygen species (ROS) such as superoxide and hydrogen peroxide upon incubation in pH 7.4 under ambient aerobic conditions. ROS generation from these compounds was sensitive to structural modifications at the 3-amino position and a 2-aryl substituent promoted ROS generation. A number of these compounds were found to induce DNA damage in the presence of Cu(II) without any added reducing agent. Our data suggests that 2-aryl-3-amino-1,4-naphthoquinones' propensity to produce ROS correlated well with its DNA damage inducing ability. 2-Phenyl-3-pyrrolid-1-yl-1,4-naphthoquinone (22) was found to damage DNA at 1 mu M suggesting that these compounds may have therapeutic relevance in targeting cancers which over-express Cu(II) (C) 2012 Elsevier Ltd. All rights reserved.
• Substituent-Enabled Oxidative Dehydrogenative Cross-Coupling of 1,4-Naphthoquinones with Alkenes
  作者：Chi Zhang、Meining Wang、Zhoulong Fan、Li-Ping Sun、Ao Zhang

  DOI：10.1021/jo501419s

  日期：2014.8.15

  A Rh-catalyzed oxidative dehydrogenative cross-coupling of 1,4-naphthquinones with alkenes was achieved by using a substituent-enabled C(sp(2))-H functionalization (SEF) strategy. The method shows high functional group tolerance, broad substrate scope, and great potential for further functional transformations.