6-amino>-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-dione | 109519-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-amino>-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 6--5-formyl-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione；6-[benzyl(trans-cinnamyl)amino]-5-formyl-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione；4-[benzyl-[(E)-3-phenylprop-2-enyl]amino]-1,3-dimethyl-2,6-dioxopyrimidine-5-carbaldehyde
• CAS: 109519-66-6
• 化学式: C₂₃H₂₃N₃O₃
• 分子量: 389.454
• InChiKey: XJKUQCLYOLKBNT-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino>-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 在 lead(IV) acetate 、 盐酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (5S,6R)-8-benzyl-10,12-dimethyl-4-(4-methylphenyl)sulfonyl-5-phenyl-3,4,8,10,12-pentazatricyclo[7.4.0.02,6]trideca-1(9),2-diene-11,13-dione
  参考文献：
  名称：

  Studies on pyridopyrimidines. I Synthesis of pyrazolo(3',4':4,5)pyrido(2,3-d)pyrimidine derivatives.

  摘要：

  6-烯丙基氨基嘧啶-2，4(1H，3H)-二酮-5-羰基醛的对甲苯基肼与四乙酸铅反应得到吡唑并[3'，4' : 4，5]吡啶并[2，3-d]嘧啶衍生物，收率良好。在该反应中，腈酰亚胺中间体发生了分子内 1，3-二极加成反应，生成了三环杂环。吡唑并[3,4-d]嘧啶并[4,5-b]氮杂卓衍生物也是通过相应的 6-烯基氨基嘧啶-2,4(1H,3H)-二酮-5-甲醛的对甲苯基肼的类似氧化反应制备的。

  DOI：

  10.1248/cpb.34.3994
• 作为产物：
  描述：

  苄基-((E)-3-苯基-烯丙基)-胺 、 6-氯-5-甲酰基-1,3-二甲基尿嘧啶 以 乙醇 为溶剂， 反应 12.0h， 以60%的产率得到6-amino>-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Studies on pyridopyrimidines. I Synthesis of pyrazolo(3',4':4,5)pyrido(2,3-d)pyrimidine derivatives.

  摘要：

  6-烯丙基氨基嘧啶-2，4(1H，3H)-二酮-5-羰基醛的对甲苯基肼与四乙酸铅反应得到吡唑并[3'，4' : 4，5]吡啶并[2，3-d]嘧啶衍生物，收率良好。在该反应中，腈酰亚胺中间体发生了分子内 1，3-二极加成反应，生成了三环杂环。吡唑并[3,4-d]嘧啶并[4,5-b]氮杂卓衍生物也是通过相应的 6-烯基氨基嘧啶-2,4(1H,3H)-二酮-5-甲醛的对甲苯基肼的类似氧化反应制备的。

  DOI：

  10.1248/cpb.34.3994

文献信息

• A Facile Cyclopropane Ring-Formation by the Thermal Reaction of 2-(Alk-2-enylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxaldehydes with Tosylhydrazine
  作者：Bin Sun、Kenji Adachi、Michihiko Noguchi

  DOI：10.1055/s-1997-1507

  日期：1997.1

  A facile intramolecular cyclopropane ring formation was accomplished by the reaction of heterocyclic aldehydes bearing alkenylamino moieties with tosylhydrazine in less polar solvents. The thermally induced isomerization of hydrazone to azomethine imine and its intramolecular cycloaddition reaction leading to a pyrazolodine derivative was suggested as a key step for the cyclopropane ring formation.

  通过带有烯基氨基部分的杂环醛与甲苯磺酰肼在极性较小的溶剂中反应，可以轻松形成分子内环丙烷环。腙的热诱导异构化为偶氮甲碱亚胺及其产生吡唑啉衍生物的分子内环加成反应被认为是环丙烷环形成的关键步骤。
• Preparation of Pyrazolo[3′,4′ : 4,5]pyrido[2,3-<i>d</i>]pyrimidines by the Intramolecular Reaction of Azomethine Imines in a 2,4(1<i>H</i>,3<i>H</i>)-Pyrimidinedione System
  作者：Michihiko Noguchi、Kazuo Yamada

  DOI：10.1055/s-1993-25819

  日期：——

  A facile synthetic route to substituted 6,8-dimethyl-3,3a,4, 5-dihydro-2H-pyrazolo[3′,4′:4,5]pyrido[2,3-d]pyrimidine-] 7,9(6H,8H)-di-ones is described based on an intramolecular azomethine imine cyclization followed by dehydrogenation. The azomethine imine intermediates are given by the thermal 1,2-hydrogen shift of the hydrazones, which are formed from the reaction of 6-allylamino-5-formyl-1, 3-dimethyl-2,4(1H,3H)-pyrimidinediones and hydrazines 2.

  基于分子内氮亚胺环化和脱氢反应，描述了取代的 6,8-二甲基-3,3a,4,5-二氢-2H-吡唑并[3′,4′:4,5]吡啶并[2,3-d]嘧啶-]7,9(6H,8H)-二酮的简便合成路线。偶氮亚胺中间体是由 6-烯丙基氨基-5-甲酰基-1,3-二甲基-2,4(1H,3H)-嘧啶二酮和肼 2 反应生成的肼的 1,2-氢热移给出的。
• Studies on fused pyrimidine derivatives. Part 13. Thermal ene reaction of 6-(alk-2-enylamino)-5-[(substituted imino)methyl]-1,3-dimethylpyrimidine-2,4(1H,3H)-diones leading to pyrimido[4,5-b]azepines
  作者：Tomonori Inazumi、Etsuko Harada、Takashi Mizukoshi、Yoshiaki Kuroki、Akikazu Kakehi、Michihiko Noguchi

  DOI：10.1039/p19940000565

  日期：——

  3-dimethyl-5-[(substituted imino)methyl]pyrimidine-2,4(1H,3H)-diones, obtained from 6-(alk-2-enylamino)-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-diones 1 and primary amines, participate in the intramolecular ene reaction (Type III) leading to pyrimido[4,5-b]azepine derivatives.

  由6-（烷-2-烯基氨基）获得的6-（烷-2-烯基氨基）-1,3-二甲基-5-[（取代的亚氨基）甲基]嘧啶-2,4（1 H，3 H）-二酮）-5-甲酰基-1,3-二甲基嘧啶-2,4（1 H，3 H）-二酮1和伯胺参与分子内烯反应（III型），导致嘧啶基[4,5- b ]氮杂衍生品。
• Studies on fused pyrimidine derivatives. Part 12. Reaction of 6-(alk-2-enylamino)-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-diones with α-amino acid derivatives
  作者：Tomonori Inazumi、Kazuo Yamada、Yoshiaki Kuroki、Akikazu Kakehi、Michihiko Noguchi

  DOI：10.1039/p19940000557

  日期：——

  The reactions of 6-(alk-2-enylamino)-5-formyl-1,3-dimethylpyrimidine-2.4(1 H,3H)-diones 1 with alpha-amino acid derivatives are described. The reaction of compounds of 1 with N-substituted amino acid derivatives affords azomethine ylides through well known condensation processes. A similar reaction with N-unsubstituted amino acid derivatives gives pyrimido [4,5-b]azepine derivatives via an intramolecular ene reaction of the imines. obtained from diones 1 and N-unsubstituted amino acid derivatives. The reaction profiles depend upon the N-substituent patterns of the amino acid derivatives utilised.
• Inazumi Tomonori, Harada Etsuko, Mizukoshi Takashi, Kuroki Yoshiaki, Kake+, J. Chem. Soc. Perkin Trans. 1, (1994) N 5, S 565-570
  作者：Inazumi Tomonori, Harada Etsuko, Mizukoshi Takashi, Kuroki Yoshiaki, Kake+

  DOI：——

  日期：——