1,3-dimethyl-2,4-dioxo-6[(triphenylphosphoranylidene)-amino]-1,2,3,4-tetrahydropyrimidine | 99747-54-3

• 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: 1,3-dimethyl-2,4-dioxo-6[(triphenylphosphoranylidene)-amino]-1,2,3,4-tetrahydropyrimidine
• 英文别名: 1,3-dimethyl-2,4-dioxo-6-<(triphenylphosphoranylidene)amino>-1,2,3,4-tetrahydropyrimidine；1,3-dimethyl-2,4-dioxo-6-<(triphenylphosphoranylidene)amino>pyrimidine；6-<(Triphenylphosphoranylidene)amino>uracil；1,3-dimethyl-6-phosphoranylideneaminouracil；1,3-Dimethyl-6-(triphenylphosphoranylideneamino)-pyrimidin-2,4(1,3H)-dione；1,3-dimethyl-6-(triphenylphosphoranylideneamino)uracil；1,3-dimethyl-5-triphenylphosphoranylideneaminouracil；1,3-Dimethyl-4-triphenylphosphoranylideneamino-pyrimdine-2,4-dione；1,3-dimethyl-6-[(triphenyl-λ5-phosphanylidene)amino]pyrimidine-2,4-dione
• CAS: 99747-54-3
• 化学式: C₂₄H₂₂N₃O₂P
• 分子量: 415.431
• InChiKey: VJPMTEATFWLSPM-UHFFFAOYSA-N

物化性质

• 熔点：
  238 °C(Solv: ethanol (64-17-5))
• 沸点：
  552.7±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-2,4-dioxo-6[(triphenylphosphoranylidene)-amino]-1,2,3,4-tetrahydropyrimidine 在 溶剂黄146 、 三氟乙酸 作用下， 反应 6.0h， 以62%的产率得到1,3-二甲基-6-氨基脲嘧啶
  参考文献：
  名称：

  Pyrido[2,3-d]pyrimidines, II. One step synthesis of pyrido[2,3-d]pyrimidines and pyrimido[4,5-b]quinolines from 6-amino uracils

  摘要：

  Reduction of 6-azidouracils 2 with hydrogen palladium or sodium dithionite afforded the corresponding 6-aminouracils 5 which could also be obtained by reaction of 2 with triphenylphosphane via phosphazenes and subsequent hydrolysis (Staudinger reaction). The use of trimethylphosphite instead of phosphanes yields with 2b the expected trimethoxyphosphazene 3c, whereas 2a reacts to the phosphonoaminopyrimidine 4. The syntheses of 5-hydroxy pyrido[2,3-d]pryimidine-2,4,7-triones 6, pyrido [2,3-d]pyrimidine-2,4,5-triones 8, cyclopenta[e]pyrido[2,3-d]pyrimidin-2,4,5-triones 7a, c, and tetrahydro-pyrimido[4,5-b]quinolin-2,4,5-triones 7b,d by condensation of 6-aminouracils 5 with malonates, ethylaceto/benzoylacetate, ethyl 2-oxocyclopentanecarboxylate and ethyl 2-oxocyclohexanecarboxylate, respectively, are described.

  DOI：

  10.1007/bf00807031
• 作为产物：
  描述：

  1,3-二甲基-6-氨基脲嘧啶 、 三苯基二氯化膦 在 六氯乙烷 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以63%的产率得到1,3-dimethyl-2,4-dioxo-6[(triphenylphosphoranylidene)-amino]-1,2,3,4-tetrahydropyrimidine
  参考文献：
  名称：

  Dihalotriphenylphosphoranes in heterocyclic synthesis. Part 8. Reactions of uracils. 6. New ring transformations of 6-aminouracils with acetylenedicarboxylates to pyridinedionates and pyrrolo[3,4-c]pyridines. Some revised constitutions

  摘要：

  DOI：

  10.1021/jo00352a005

文献信息

• Iminophosphorane-Mediated Synthesis of Pyrido[2,3-<i>d</i>]pyrimidine Derivatives
  作者：Pedro Molina、Maria Jesús Vilaplana

  DOI：10.1055/s-1990-26908

  日期：——

  The 5-(2-nitroethenyl)-6-[(triphenylphosphoranylidene)amino]-pyrimidine derivative 3, prepared from 1,3-dimethyl-2,4-dioxo-6-[(triphenylphosphoranylidene)amino] -1,2,3,4-tetrahydropyrimidine (1) and 1-dimethylamino-2-nitroethylene (2), reacts with aryl isocyanates 4 to give 7-arylamino-1, 3-dimethyl-2,4-dioxo-6-nitro-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidines 6 in good yield.

  5-(2-硝基乙烯基)-6-[(三苯基膦亚基)氨基]-嘧啶衍生物 3 由 1,3-二甲基-2,4-二氧代-6-[(三苯基膦亚基)氨基] -1,2,3、与芳基异氰酸酯 4 反应生成 7-芳基氨基-1,3-二甲基-2,4-二氧代-6-硝基-1,2,3,4-四氢吡啶并[2,3-d]嘧啶 6，收率良好。
• Heterocondensed uracil betaines by three component reaction: iminophosphorane, heteroarene, isocyanate
  作者：Heinrich Wamhoff、Andreas Schmidt、Martin Nieger

  DOI：10.1016/0040-4039(91)80015-x

  日期：1991.1

  1,3-Dimethyl-6(triphenylphosphoranylideneamino)uracil 1 affords with pyridines and the isocyanates 2a-f in a novel type of a three component reaction pyrido[1,2-f]pyrimido-[4,5-d]pyrimidines 5a-h (X-ray analysis of 5a).

  1,3-二甲基-6（三苯基正膦基亚氨基氨基）尿嘧啶1以新型的三组分反应吡啶基[1,2-f]嘧啶基-[4,5-d]嘧啶5a-提供吡啶和异氰酸酯2a-f。h（5a的X射线分析）。
• Direct regioselective arylsulfenylation and arylselenenylation at 5-position of uracils mediated by silver reagents
  作者：Chun Ho Lee、Yong Hae Kim

  DOI：10.1016/s0040-4039(00)79934-5

  日期：1991.5

  Electrophilic additions of phenylsulfenyl chloride or phenylselenenyl chloride to a carbon-carbon double bond of C-5,6 region of uracils in the presence of silver reagents such as Ag2O, AgBF4, or AgOCOCF3 directly gave the corresponding 5-phenylsulfydryl- or 5-phenylselenenyl uracils in good yields.
• Reactions of uracils. 21. Zwitterionic heteropolycyclic uracils by a novel three-component reaction: iminophosphorane, isocyanate, heteroarene
  作者：Heinrich Wamhoff、Andreas Schmidt

  DOI：10.1021/jo00077a013

  日期：1993.12

  The novel three-component reaction of (uracil-6-ylimino)phosphorane 1, isocyanate 2, and (substituted) pyridines gives, in a one-pot procedure, a variety of new pyrido[ 1',2':3,41 pyrimido[4,5-d]pyrimidines 3-11. The zwitterionic ground state of these new ring systems is i.a. established by means of solvatochromism, Hammett correlations, NMR, and X-ray analysis. Replacement of the pyridine by isoquinoline and phthalazine gives access to the novel ring systems pyrimido[4',5':4,5]pyrimido-[6,1-a]isoquinoline and -phthalazine, which are formed as dihydro derivatives (14, 15) or as zwitterions (13,17), depending on there action conditions. Oxidative cleavage of the phthalazine 15 in nitrobenzene affords the pyrimido[4,5-d]pyrimidines 16.
• A facile synthesis of pyrrolo[3,2-d]pyrimidines from 6-azidouracils and ylide phosphoranes
  作者：Wafaa M. Abdou、Amin F. M. Fahmy、Azza A. Kamel

  DOI：10.1002/hc.10048

  日期：——

  AbstractA series of the title compounds, 9‐deazaxanthines, was regioselectively prepared in reasonable yields as major products from the reactions of 6‐azidouracils 1a,b with stabilized ester‐2a,b or keto‐2c ylide phosphoranes and a moderated phosphorus ylide 3, instead of the expected triazoles. Side products were also observed wherein pyrimido[5,4‐g]pteridine‐2,4,5,7‐tetrone (15) and other fused ring systems or acyclic‐substituted uracil derivatives were isolated. A comparative study on the reactivity of 1a in analogy to 1b toward phosphoranes is also described. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:357–365, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10048