2-甲基-3-(甲基氨基)-1,4-萘醌 | 1694-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-甲基-3-(甲基氨基)-1,4-萘醌
• 英文名称: 2-methylamino-3-methyl-1,4-naphthoquinone
• 英文别名: 1,4-Naphthalenedione, 2-methyl-3-(methylamino)-；2-methyl-3-(methylamino)naphthalene-1,4-dione
• CAS: 1694-01-5
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: WGCISMWFRZYHJR-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C
• 沸点：
  346.2±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 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：

  2-甲基-3-(甲基氨基)-1,4-萘醌 在 吡啶 、 硫酸 、 水 、 溶剂黄146 作用下， 生成 2-benzoyloxy-3-methyl-[1,4]naphthoquinone
  参考文献：
  名称：

  Asano; Hase, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 59,60; dtsch. Ref. S. 55

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(二甲氨基)-3-甲基萘-1,4-二酮 以 苯 为溶剂， 反应 12.0h， 以97%的产率得到2-甲基-3-(甲基氨基)-1,4-萘醌
  参考文献：
  名称：

  Photolysis of 2-dialkylamino-3-methyl-1,4-naphthoquinones

  摘要：

  The photolysis of 2-dialkylamino-1,4-naphthoquinones is significantly more efficient when a methyl group is at C3. The quantum yields are 2-6 times greater than for 2-dialkylaminonaphthoquinones lacking a methyl group. 2-Monoalkyl-amino-1,4-naphthoquinones also undergo photochemical dealkylation.

  DOI：

  10.1007/bf00963513

文献信息

• One-Step Synthesis of 1,2,3,4-Tetrahydrobenzo(g)quinazoline-5,10-dione Derivatives from Vitamin K3.
  作者：Shunsaku OHTA、Yasunari HINATA、Masayuki YAMASHITA、Ikuo KAWASAKI、Yoko JINDA、Shinobu HORIE

  DOI：10.1248/cpb.42.1730

  日期：——

  The reactions of 2-halogenonaphthoquinones (5, 13, 14 and 15) and 2-methyl-1, 4-naphthoquinone (20; vitamin K3) with primary and secondary amines were examined. 1, 3-Dialkyl-1, 2, 3, 4-tetrahydrobenzo[g]quinazoline-5, 10-diones (9) were obtained in moderate yields by treating 20 with formaldehyde in primary amines. A plausible reaction path-way is also presented.

  对2-卤代萘醌（5、13、14和15）和2-甲基-1,4-萘醌（20；维生素K3）与一级和二级胺的反应进行了研究。通过在一级胺中用甲醛处理20，获得了1,3-二烷基-1,2,3,4-四氢苯并[g]喹唑啉-5,10-二酮（9），产率适中。同时也提出了一个合理的反应路径。
• n-alkylamino analogs of Vitamin K3: Electrochemical, DFT and anticancer activity of their oxidized and one electron reduced form
  作者：Dattatray Chadar、Priyabrata Banerjee、Sourav Kr. Saha、Sujit Bhand、Rajendra Patil、Sunita Salunke-Gawali

  DOI：10.1016/j.molstruc.2018.11.024

  日期：2019.3

  Abstract Synthesis, characterization and anticancer activity of reduced form of n-alkylamino analogs of Vitamin K3 (1Na to 8Na) are undertaken. Molecular structure and molecular association of oxidized form of 2-ethylamino-3-methyl-1,4-naphthoquinone (2) and 2-hexylamino-3-methyl-1,4-naphthoquinone (6) were studied by single crystal X-ray analysis. 2 crystallize in monoclinic C2/c and 6 in P21 space

  摘要 进行了还原形式的维生素 K3 正烷基氨基类似物（1Na 至 8Na）的合成、表征和抗癌活性。2-乙基氨基-3-甲基-1,4-萘醌(2)和2-己氨基-3-甲基-1,4-萘醌(6)氧化形式的分子结构和分子缔合研究了单晶X射线分析。2 在单斜 C2/c 中结晶，6 在 P21 空间群中结晶。使用钠金属作为还原剂在 0 °C 的甲醇中合成了 8 种 2-(n-烷基氨基)-3-甲基-1,4-萘醌 (1Na 至 8Na) 同系物的还原形式。从它们的 EPR 光谱证实了 1 到 6 中萘半醌自由基的形成。1 至 6 的多晶粉末 X 带 EPR 光谱在 133 K 下显示信号 ~2.0020 ± 0.0026。2-(n-烷基氨基)-3-methyl-1 的抗癌活性，
• Photo-Oxidation of 2-Methylamino-3-(1-piperidinylmethyl)-1,4-naphthoquinone.
  作者：Shunsaku OHTA、Yasunari HINATA、Ikuo KAWASAKI、Masayuki YAMASHITA

  DOI：10.1248/cpb.42.2360

  日期：——

  2-Methylamino-3-(1-piperidinylmethyl)-1, 4-naphthoquinone (7) was prepared via several steps from 2-methyl-1, 4-naphthoquinone (vitamin K3, 3). The quinone (7) was photochemically oxidized to 2-methylamino-3-(1-piperidinylcarbonyl)-1, 4-naphthoquinone (8) and/or 2-alkoxycarbonyl-3-methylamino-1, 4-naphthoquinone (9), depending on the solvent used.

  2-甲基氨基-3-(1-哌啶基甲基)-1, 4-萘醌 (7) 由 2-甲基-1, 4-萘醌（维生素 K3, 3）通过几个步骤制备。醌(7)被光化学氧化成2-甲基氨基-3-(1-哌啶基羰基)-1, 4-萘醌(8)和/或2-烷氧基羰基-3-甲基氨基-1, 4-萘醌(9)，具体取决于与所使用的溶剂有关。
• Sharma, Upendra; Katoch, Deepali; Sood, Swati, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 11, p. 1431 - 1440
  作者：Sharma, Upendra、Katoch, Deepali、Sood, Swati、Kumar, Neeraj、Singh, Bikram、Thakur, Archana、Gulati, Arvind

  DOI：——

  日期：——
• Synthesis and characterization of n-alkylamino derivatives of vitamin K3: Molecular structure of 2-propylamino-3-methyl-1,4-naphthoquinone and antibacterial activities
  作者：Dattatray Chadar、Maria Camilles、Rishikesh Patil、Ayesha Khan、Thomas Weyhermüller、Sunita Salunke-Gawali

  DOI：10.1016/j.molstruc.2015.01.029

  日期：2015.4

  We would like to introduce eight analogues of n-alkylamino derivatives of vitamin K3 (2-methyl-1,4-naphthoquinone) viz, 2-(n-alkylamino)-3-methyl-1,4-naphthoquinone (where n-alkyl is methyl; LM-1, ethyl; LM-2, propyl; LM-3, butyl; LM-4, pentyl; LM-5, hexyl; LM-6, heptyl; LM-7, octyl; LM-8). All the above analogues have been successfully synthesized from vitamin K3 and characterized using different analytical techniques. Furthermore, in order to understand the mechanistic aspects of formation of LM-1 to LM-8 compounds, we could propose the mechanism. The FT-IR analysis of LM-1 to LM-8 indicate the presence of characteristic band of N-H group similar to 3287-3364 cm(-1), the variation was attributed to extensive intramolecular hydrogen bonding interaction. The molecular structure of LM-3 compound has been confirmed by single crystal X-ray diffraction analysis. LM-3 compound crystallises in triclinic space group P1. There were four independent molecules in asymmetric unit cell and their molecular interactions observed via N-H...O , C-H...O and pi-pi stacking of quinonoid rings. Pharmacological potential of all compounds has been evaluated in terms of their antibacterial activities against Pseudomonas aeruginosa and Staphylococcus aureus. All the compounds were active against both the strains while LM-2 was found to be more effective with a minimum inhibition concentration of 0.3125 mu g/mL and 0.156 mu g/mL respectively. (C) 2015 Elsevier B.V. All rights reserved.

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