6-phenyl-4,5-dihydro-1,2,4-triazin-3(2H)-one | 78831-00-2

• 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-4,5-dihydro-1,2,4-triazin-3(2H)-one
• 英文别名: 6-phenyl-4,5-dihydro-1,2,4-triazin-3-one；6-phenyl-4,5-dihydro-2H-[1,2,4]triazin-3-one；6-Phenyl-4,5-dihydro-2H-[1,2,4]triazin-3-on；6-phenyl-4,5-dihydro-2H-1,2,4-triazin-3-one
• CAS: 78831-00-2
• 化学式: C₉H₉N₃O
• mdl: MFCD01088874
• 分子量: 175.19
• InChiKey: LWMREWHCHKZSDF-UHFFFAOYSA-N

物化性质

• 熔点：
  225-226 °C
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  6-phenyl-4,5-dihydro-1,2,4-triazin-3(2H)-one 在 叔丁基过氧化氢 、 1,2-二氯乙烯 、 copper diacetate 、 potassium carbonate 作用下， 反应 24.0h， 生成 6-phenyl-1,2,4-triazin-3-one
  参考文献：
  名称：

  Tuning the Annulation Reactivity of Vinyl Azides and Carbazates: A Divergent Synthesis of Aza-pyrimidinones and Imidazoles

  摘要：

  A divergent cascade annulation has been developed using readily available vinyl azides and carbazates with a wide range of substituents. Vinyl azides were successfully applied as bifunctional partners to prepare aza-pyrimidinones via 6-ring closure with carbazates as well as to construct polyfunctionalized imidazoles via 5-ring closure with N-substituted carbazates. The aza-heterocycles were obtained with high levels of chemoselectivity and excellent yields.

  DOI：

  10.1021/acs.orglett.5b02180
• 作为产物：
  描述：

  3-(2-氧代-2-苯基乙基)-1,3-噻唑烷-2,4-二酮 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到6-phenyl-4,5-dihydro-1,2,4-triazin-3(2H)-one
  参考文献：
  名称：

  Shvaika, O. P.; Korotkikh, N. I.; Chervinskii, A. Yu., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 8, p. 1533 - 1543

  摘要：

  DOI：

文献信息

• Thieme Chemistry Journals Awardees – Where Are They Now? A Cascade Synthesis of 1,2,4-Triazin-3(2H)-ones Using Nitrogen-Substituted Isocyanates
  作者：André Beauchemin、Mohammed Dahab、Joshua Derasp

  DOI：10.1055/s-0036-1588099

  日期：——

  A cascade synthesis of 1,2,4-triazin-3(2H)-ones is reported from readily accessible α-amino ketones and phenyl carbazate as a masked N-isocyanate precursor. The mild protocol provides a simple route to products with substitution patterns which are difficult to form directly. This also presents the first N-isocyanate cascade requiring the use of acidic conditions, which accelerates formation of the

  据报道，1,2,4-triazin-3(2H)-ones 的级联合成来自容易获得的 α-氨基酮和苯甲酸苯酯作为掩蔽的 N-异氰酸酯前体。温和的协议为具有难以直接形成的替代模式的产品提供了一种简单的途径。这也呈现出需要使用酸性条件的第一个 N-异氰酸酯级联，这会加速腙中间体的形成和环化步骤。这种级联进一步强调了在形成高反应性 N-异氰酸酯中间体的反应中可以实现高度控制。
• Arylation of 1,2,4-Triazines in the Presence of AlCl₃
  作者：Ilya N. Egorov

  DOI：10.5560/znb.2014-4103

  日期：2014.8.1

  This paper presents a method for introducing toluene and bromobenzene moieties into 1,2,4- triazines as an alternative to cross-coupling reactions. It is demonstrated that the C=N bond of a wide range of 1,2,4-triazines undergoes addition of arenes in the presence of AlCl₃.

  本文介绍了一种将甲苯和溴苯分子引入 1,2,4-三嗪的方法，以替代交叉耦合反应。研究表明，在 AlCl3 的存在下，多种 1,2,4-三嗪的 C=N 键会发生茴香加成反应。
• Pharmaceutically active phenyl-thia-, oxa- or triazinones
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0080296A1

  公开（公告）日：1983-06-01

  Heterocyclic compounds of the formula wherein either X is -CR1R2and Y is -O-, -S- or-NR3-, wherein R1, R2 and R3, which may be the same of different, each is hydrogen or alkyl of up to 4 carbon atoms; or X is-O-, -S- or -NH- and Y is -CF1R2- wherein R1 and R2 have the meanings stated above; wherein either R4 is hydrogen, fluoro or chloro, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atom, and R5, R6 and R7, which may be the same or different, each is hydrogen, fluoro, chloro, bromo or iodo, or alkyl, alkenyl, halogenoalkyl, aminoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxy each of up to 6 carbon atoms, provided that R4, R5, R6 and R7 are not all hydrogen; or R4 is bromo and R5, R6 and R7 have the meanings stated above, provided that R5, R6and R7 are not all hydrogen; or R4 and R5 together, or R5 and R6 together, or R4 and R7 together, from the-CH=CH-CH=CH-group and the othertwo of R4, R5, R6 and R7 have the meanings stated above; processes for their manufacture and pharmaceutical compositions containing them. The compounds possess cardiotonic and/or antihypertensive activity.

  式中的杂环化合物 其中X为-CR1R2，Y为-O-、-S-或-NR3-，其中R1、R2和R3可以相同或不同，各自为氢或最多4个碳原子的烷基； 或 X 为-O-、-S-或-NH-，Y 为-CF1R2-，其中 R1 和 R2 具有上述含义； 其中，R4 是氢、氟或氯，或烷基、烯基、卤代烷基、氨基烷基、羟基烷基、烷氧基烷基或烷氧基，每个烷基最多 6 个碳原子；R5、R6 和 R7（可以相同或不同）各自是氢、氟、氯、溴或碘，或烷基、烯基、卤代烷基、氨基烷基、羟基烷基、烷氧基烷基或烷氧基，每个烷基最多 6 个碳原子，条件是 R4、R5、R6 和 R7 不全是氢； 或 R4 为溴，R5、R6 和 R7 具有上述含义，但 R5、R6 和 R7 并非都是氢； 或 R4 和 R5 一起，或 R5 和 R6 一起，或 R4 和 R7 一起，来自-CH=CH-CH=CH-基团，且 R4、R5、R6 和 R7 中的另外两个具有上述含义；它们的制造工艺和含有它们的药物组合物。这些化合物具有强心和/或抗高血压活性。
• Thiadiazine derivatives, and pharmaceutical compositions containing them
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0085227A1

  公开（公告）日：1983-08-10

  Heterocyclic compounds of the formula:- wherein A is a direct link, or is alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms; wherein either X is -CR1R2- and Y is -0-, -S- or -NR3-, wherein R1, R2 and R3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms; or X is-O-,-S- or-NH- and Y is-CR1R2- wherein R1 and R2 have the meanings stated above; and wherein Het is a 5- or 6- membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from nitrogen, oxygen or sulphur atoms, which ring may be unsubstituted or may bear one or two substituents as set out in claim 1, provided that when X is -CR1R2- and A is a direct link, Het is not unsubstituted 2-furyl; and salts thereof where appropriate; processes for their manufacture and pharmaceutical compositions containing them. The compounds possess cardiotonic and/or antihypertensive activity.

  分子式为：- 的杂环化合物 其中 A 为直接连接，或为 1 至 4 个碳原子的亚烷基或 2 至 4 个碳原子的烯基； 其中 X 为-CR1R2-，Y 为-0-、-S- 或-NR3-，其中 R1、R2 和 R3 可以相同或不同，各自为氢或最多 4 个碳原子的烷基； 或 X 是-O-、-S- 或-NH-，Y 是-CR1R2-，其中 R1 和 R2 具有上述含义； 其中Het是含有1、2或3个选自氮、氧或硫原子的杂原子的5-或6-成员杂环，该环可以是未取代的，也可以带有权利要求1所述的一个或两个取代基，条件是当X是-CR1R2-和A是直接连接时，Het不是未取代的2-呋喃基；及其适当的盐类；它们的制造工艺和含有它们的药物组合物。这些化合物具有强心和/或抗高血压活性。
• Thiadiazine, oxadiazine and triazine derivatives and pharmaceutical compositions containing them
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0086301A1

  公开（公告）日：1983-08-24

  Heterocyclic compounds of the formula: wherein either X is -CR1R2- and Y is -0-, -S- or -NHR3-, wherein R1, R2 and R3, which may be the same or different, each is hydrogen or alkyl of up to 4 carbon atoms; or X is -0-, -S- or -NH- and Y is -CR1R2- wherein R1 and R2 have the meanings stated above; wherein R4 and R5, which may be the same or different, each is hydrogen (but provided that R4 and R5 are not both hydrogen), or each is a group defined in claim 1 which is readily convertible into a carboxy group; processes for their manufacture; and pharmaceutical compositions containing them. The compounds possess cardiotonic and/or antihypertensive activity.

  式中X为-CR1R2-，Y为-0-、-S-或-NHR3-，其中R1、R2和R3可以相同或不同，各自为氢或最多4个碳原子的烷基；或X为-0-、-S-或-NH-，Y为-CR1R2-，其中R1和R2具有上述含义；其中R4和R5可以相同或不同，各自为氢(但条件是R4和R5不都是氢)，或各自为权利要求1中定义的基团，该基团易于转化为羧基；其制造工艺；以及含有它们的药物组合物。 这些化合物具有强心和/或抗高血压活性。