6-(N-allylbenzylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine 5-carboxaldehyde | 147743-24-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-(N-allylbenzylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine 5-carboxaldehyde
• 英文别名: 6-(N-allylbenzylamino)-5-formyl-1,3-dimethylpyrimidine-2,4-(2H,4H)-dione；6-(N-allylbenzylamino)-5-formyl-1,3-dimethylpyrimidin-2,4-(1H,3H)-dione；6-(N-allylbenzylamino)-5-formyl-1,3-dimethylpyrimidine-2,4(1H,3H)-dione；6-(allylbenzylamino)-5-formyl-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione；4-[benzyl(prop-2-enyl)amino]-1,3-dimethyl-2,6-dioxopyrimidine-5-carbaldehyde
• CAS: 147743-24-6
• 化学式: C₁₇H₁₉N₃O₃
• 分子量: 313.356
• InChiKey: BOMJOOIWAWSOAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.31
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-(N-allylbenzylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine 5-carboxaldehyde 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 52.0h， 生成 1,3-dibenzyl-6,8-dimethyl-1,2,3,4-tetrahydro-2,4-ethanopyrimido<4,5-d>pyrimidine-5,7(6H,8H)-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1039/p19940000557
• 作为产物：
  描述：

  N-烯丙基苄胺 、 6-氯-5-甲酰基-1,3-二甲基尿嘧啶 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 6-(N-allylbenzylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine 5-carboxaldehyde
  参考文献：
  名称：

  Preparation of Pyrazolo[3′,4′ : 4,5]pyrido[2,3-d]pyrimidines by the Intramolecular Reaction of Azomethine Imines in a 2,4(1H,3H)-Pyrimidinedione System

  摘要：

  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。

  DOI：

  10.1055/s-1993-25819

文献信息

• Mechanistic considerations on the azepine-ring formation through the ene reactions at the periphery of heterocyclic systems
  作者：Michihiko Noguchi、Takashi Mizukoshi、Takehiko Uchida、Yoshiaki Kuroki

  DOI：10.1016/0040-4020(96)00772-7

  日期：1996.10

  A mechanistic proposal for the azepine-ring formation at the periphery of heterocyclic systems is described. Intramolecular thermal ene reactions of O-alkyl oximes 5 and 6, N′,N′-disubstituted hydrazone 11, and N-tosyl imines, obtained from aldehydes of pyrido[1,2-a]pyrimidine1, pyridine 2, and pyrimidine system 3, have been developed. These reactions reveal to be a fruitful and stereoselective approach

  描述了在杂环系统的外围形成氮杂环的机械方案。从吡啶并[1,2- a ]嘧啶1，吡啶2和嘧啶体系的醛类获得的O-烷基肟5和6，N '，N'-二取代11和N-甲苯磺酰基亚胺的分子内热烯反应3， 已经开发了。这些反应揭示了对杂环稠合的a庚因衍生物的丰硕且立体选择性的方法。通过动力学研究以及模型反应的分子轨道计算（PM3方法），已经完成了关于通过亚胺和羰基烯反应形成a庚环的机理的讨论。这些结果证明两种烯反应均以协同方式进行。
• 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。
• Synthesis of some novel annulated pyrido[2,3-<i>d</i>]pyrimidines via stereoselective intramolecular hetero Diels–Alder reactions of 1-oxa-1,3-butadienes
  作者：Mohit L Deb、Pulak J Bhuyan

  DOI：10.3762/bjoc.6.11

  日期：——

  Some novel annulated pyrido[2,3-d]pyrimidines 6 and 7 were synthesized stereoselectively by intramolecular hetero Diels-Alder reactions involving 1-oxa-1,3-butadienes.

  通过涉及 1-oxa-1,3-丁二烯的分子内杂 Diels-Alder 反应立体选择性合成了一些新型环状吡啶并[2,3-d]嘧啶 6 和 7。
• Competitive thermal ene reaction and Diels–Alder reactions of 2-[N-(alk-2-enyl)benzylamino]-3-vinylpyrido[1,2-a]pyrimidin-4(4H)-ones
  作者：Michihiko Noguchi、Toshiya Sunagawa、Ryosuke Akao、Hisashi Yamada、Hidetoshi Yamamoto、Akikazu Kakehi

  DOI：10.1016/j.tet.2007.03.037

  日期：2007.5

  Thermal reaction of 2-[N-(alk-2-enyl)benzylamino]-3-(2-substituted and 2,2-disubstituted)vinylpyrido[1,2-a]pyrimidin-4(4H)-ones gave azepine, the desired ene products, and/or pyran derivatives. The formation of the latter was responsible for the [4+2] cycloaddition reaction between the α,β-unsaturated ester carbonyl moiety as a diene part and the alkenylamino moiety as an ene one. The reaction features

  2- [ N-（烷-2-烯基）苄氨基] -3-（2-取代和2,2-二取代）乙烯基吡啶并[1,2 - a ]嘧啶-4（4 H）-的热反应得到氮杂gave ，所需的烯产物和/或吡喃衍生物。后者的形成负责作为二烯部分的α，β-不饱和酯羰基部分与作为烯基的烯基氨基部分之间的[4 + 2]环加成反应。反应特征取决于乙烯基和链烯基对应物上的取代基的种类。乙烯基部分上的强吸电子取代基或烯基上的供电子取代基将反应特征从烯反应转变为杂狄尔斯-阿尔德反应。
• Noguchi, Michihiko; Akao, Ryosuke; Gotoh, Mitsuhiro, Journal of Chemical Research, Miniprint, 2000, # 9, p. 1023 - 1032
  作者：Noguchi, Michihiko、Akao, Ryosuke、Gotoh, Mitsuhiro、Kawamoto, Hideyasu、Kakehi, Akikazu

  DOI：——

  日期：——