6-phenyl-1,2,4-triazin-5-one | 36993-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-phenyl-1,2,4-triazin-5-one
• 英文别名: 6-phenyl-2H-1,2,4-triazin-5-one；6-phenyl-4H-1,2,4-triazin-5-one
• CAS: 36993-97-2
• 化学式: C₉H₇N₃O
• mdl: MFCD08457754
• 分子量: 173.174
• InChiKey: MVAQKCBXFGRWER-UHFFFAOYSA-N

物化性质

• 熔点：
  208 °C(Solv: ethanol (64-17-5))
• 沸点：
  289.5±23.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吲哚 、 萘普生 、 6-phenyl-1,2,4-triazin-5-one 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以33%的产率得到3-(1H-indol-3-yl)-2-[2-(6-methoxynaphthalen-2-yl)propionyl]-6-phenyl-3,4-dihydro-2H-[1,2,4]triazin-5-one
  参考文献：
  名称：

  Diastereoselective synthesis of 3-substituted acylamino-3,4-dihydro-1,2,4-triazinones

  摘要：

  6-Phenyl-1,2,4-triazin-5(4H)-one 1 reacts with C-nucleophiles, such as indole, in the presence of N-acetylamino acids, to yield 2-acyl-3-indolyl-6-phenyl-3,4-dihydro-1,2,4-triazin-5(4H)-ones 2-6 with high diastereoselectivity.

  DOI：

  10.1016/j.mencom.2008.03.017
• 作为产物：
  描述：

  5-cyanoimino-6-phenyl-2,5-dihydro-1,2,4-triazine 在 盐酸 作用下， 反应 0.33h， 以72%的产率得到6-phenyl-1,2,4-triazin-5-one
  参考文献：
  名称：

  Nucleophilic substitution of hydrogen in the reaction of 1,2,4-triazin-4-oxides with cyanamide

  摘要：

  It was shown that cyanamide can successfully be used in reactions of nucleophilic substitution of hydrogen with 1,2,4-triazin-4-oxides in the presence of a base to give 5-cyanoimino-1,2,4-triazines. It was found by C-13 NMR spectroscopy that these compounds and their alkylation products at the cyclic nitrogen atom exist in the form of 5-cyanoimino-2,5-dihydro-1,2,4-triazines.

  DOI：

  10.1007/bf02494908

文献信息

• Asymmetric induction in the reactions of azinones with C-nucleophiles
  作者：O. N. Chupakhin、I. N. Egorov、V. L. Rusinov、P. A. Slepukhin

  DOI：10.1007/s11172-010-0195-z

  日期：2010.5

  acylating agents on the course of addition of C-nucleophiles to 1,2,4- and 1,3,5-triazinones, as well as to quinoxalin-2(1H)-one, was studied. A series of new azinone derivatives was obtained. A method for the preparation of diastereomerically pure addition products of indoles to 1,2,4-triazinones and quinoxalin-2(1H)-one in the presence of N-Ts-L-amino acid acyl chlorides was suggested.

  研究了酰化剂对 C-亲核试剂添加到 1,2,4-和 1,3,5-三嗪酮以及喹喔啉-2(1H)-one 过程中的影响。获得了一系列新的吖嗪酮衍生物。提出了一种在 N-Ts-L-氨基酸酰氯存在下制备吲哚到 1,2,4-三嗪酮和喹喔啉-2(1H)-one 的非对映异构纯加成产物的方法。
• Asymmetric triazines—XIII
  作者：Raffaello Fusco、Silvano Rossi

  DOI：10.1016/0040-4020(58)80016-2

  日期：1958.1

  The reaction of phosphorus pentachloride with some 3:5-disubstituted-4-nitrosopyrazoles (dimethyl, diphenyl, methyl phenyl and phenyl carbomethoxy) has been investigated. Formation of a new class of compounds, 1-chloro-4-cyano-2:3-diazabuta-1:3-dienes, is described. By treatment with ammonia and subsequent alkali-induced cyclisation these substances are converted into 5-amino-as-triazines and reactions

  研究了五氯化磷与一些3：5-二取代的4-亚硝基吡唑（二甲基，二苯基，甲基苯基和苯基碳甲氧基）的反应。描述了新型化合物1-氯-4-氰基-2：3-二氮杂丁-1：3-二烯的形成。通过与氨和随后碱诱导的环化处理，这些物质被转化成5-氨基作为-triazines和后者的反应进行了研究。
• Synthesis and Crystal Structure of (S)-2-((S)-2-(N-Ts-Amino)-3-methylbutanoyl)-3-(1H-indol-3-yl)-6-phenyl-3,4-dihydro-1,2,4-triazin-5(2H)-one
  作者：Ilya N. Egorov、Vladimir L. Rusinov、Pavel A. Slepukhin、Oleg N. Chupakhin

  DOI：10.1007/s10870-010-9741-7

  日期：2010.4

  The diastereoselective synthesis, NMR and X-ray structure of (S)-2-((S)-2-(N-Ts-amino)-3-methylbutanoyl)-3-(1H-indol-3-yl)-6-phenyl-3,4-dihydro-1,2,4-triazin-5(2H)-one—a potential antivirus agent are reported. The compound crystallizes in the triclinic space group P1 with unit cell parameters: a = 5.9259(6) Å, b = 9.6370(12) Å, c = 12.9541(9) Å, α = 109.210(9)°, β = 90.804(7)°, γ = 105.074(10)° and Z = 1. The diastereoselective synthesis, NMR and X-ray structure of (S)-2-((S)-2-(N-Ts-Amino)-3-methylbutanoyl)-3-(1H-indol-3-yl)-6-phenyl-3,4-dihydro-1,2,4-triazin-5(2H)-one—a potential antivirus agent are reported.

  报告了(S)-2-((S)-2-(N-Ts-氨基)-3-甲基丁酰基)-3-(1H-吲哚-3-基)-6-苯基-3,4-二氢-1,2,4-三嗪-5(2H)-酮--一种潜在抗病毒剂的非对映选择性合成、核磁共振和 X 射线结构。该化合物在三菱空间群 P1 中结晶，其单胞参数为：a = 5.9259(6) 埃，b = 9.6370(12) Å, c = 12.9541(9) Å, α = 109.210(9)°, β = 90.804(7)°, γ = 105.报告了(S)-2-((S)-2-(N-Ts-氨基)-3-甲基丁酰基)-3-(1H-吲哚-3-基)-6-苯基-3,4-二氢-1,2,4-三嗪-5(2H)-酮--一种潜在抗病毒剂的非对映选择性合成、核磁共振和 X 射线结构。
• TAYLOR, E. C.;MACOR, J. E., J. HETEROCYCL. CHEM., 1985, 22, N 2, 409-411
  作者：TAYLOR, E. C.、MACOR, J. E.

  DOI：——

  日期：——
• NEUNHOEFFER H.; BOEHNISCH V., J. LIEBIGS ANN. CHEM. <JLAC-BF>, 1976, NO 1, 153-162
  作者：NEUNHOEFFER H.、 BOEHNISCH V.

  DOI：——

  日期：——