1,1,1-Triphenyl-3,4-bis(methoxycarbonyl)-2-aza-1λ⁵-phosphabuta-1,3-diene | 152975-96-7

• 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: 1,1,1-Triphenyl-3,4-bis(methoxycarbonyl)-2-aza-1λ⁵-phosphabuta-1,3-diene
• 英文别名: dimethyl (Z)-2-[(triphenyl-lambda5-phosphanylidene)amino]but-2-enedioate；dimethyl (Z)-2-[(triphenyl-λ5-phosphanylidene)amino]but-2-enedioate
• CAS: 152975-96-7
• 化学式: C₂₄H₂₂NO₄P
• 分子量: 419.417
• InChiKey: ZTQMWEGMVAKYTA-PYCFMQQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1-Triphenyl-3,4-bis(methoxycarbonyl)-2-aza-1λ⁵-phosphabuta-1,3-diene 在 肼 作用下， 以 乙醇 为溶剂， 生成 [2-{[4-[1-Methoxycarbonyl-meth-(Z)-ylidene]-5-oxo-1-propyl-imidazolidin-(2E)-ylidene]-hydrazono}-5-oxo-1-propyl-imidazolidin-(4Z)-ylidene]-acetic acid methyl ester
  参考文献：
  名称：

  由衍生自 b-氨基酸的 N-乙烯基磷腈合成 N-官能化碳二亚胺、乙内酰脲、1,3-二氮杂环丁烷和咪唑烷衍生物

  摘要：

  Synthesis of N-vinylic carbodiimides through Aza-Wittig reaction of N-vinylic phosphazenes with isocyanates is reported. These heterocumulenes are used for the preparation of unsymmetrical ureas and nitrogen heterocycles such as hydantoins, 1,3-diazetidines, imidazolidinones, and bis-imidazolidinone azines.

  DOI：

  10.3987/com-01-9264
• 作为产物：
  描述：

  Azidofumarsaeure-dimethylester 、 三苯基膦 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到1,1,1-Triphenyl-3,4-bis(methoxycarbonyl)-2-aza-1λ⁵-phosphabuta-1,3-diene
  参考文献：
  名称：

  Synthesis and Reactivity of Electron-Poor 2-Azadienes. [4 + 2] Cycloaddition Reactions with Alkenes and Enamines

  摘要：

  Electron deficient 2-azadienes derived from beta-amino acids 3 are obtained by aza-Wittig reaction of N-vinylic phosphazenes 4 with carbonyl compounds. Inverse electron demand Diels-Alder reaction of azadienes 3 with trans-cyclooctene 7 and cis,trans-cyclooctadiene 8 leads to the formation of trans-cycloalkanotetrahydropyridines 10. Heterodienes 3 also react with enamines 13, 14, and 18 affording pyridine derivatives 16, 17, and 20 in a regioselective fashion. Norbornadiene 11, a less strained olefin than cycloalkenes 7 and 8, requires the presence of lithium perchlorate as catalyst in a nonaqueous solvent like ether, to give cycloadducts 12.

  DOI：

  10.1021/jo00113a017

文献信息

• Synthesis and Reactivity of Electron-Poor 2-Azadienes. [4 + 2] Cycloaddition Reactions with Alkenes and Enamines
  作者：Francisco Palacios、Itziar Perez de Heredia、Gloria Rubiales

  DOI：10.1021/jo00113a017

  日期：1995.4

  Electron deficient 2-azadienes derived from beta-amino acids 3 are obtained by aza-Wittig reaction of N-vinylic phosphazenes 4 with carbonyl compounds. Inverse electron demand Diels-Alder reaction of azadienes 3 with trans-cyclooctene 7 and cis,trans-cyclooctadiene 8 leads to the formation of trans-cycloalkanotetrahydropyridines 10. Heterodienes 3 also react with enamines 13, 14, and 18 affording pyridine derivatives 16, 17, and 20 in a regioselective fashion. Norbornadiene 11, a less strained olefin than cycloalkenes 7 and 8, requires the presence of lithium perchlorate as catalyst in a nonaqueous solvent like ether, to give cycloadducts 12.
• Preparation and reactivity of electron-poor 2-azadienes. Diels-Alder reaction with trans-cyclooctene.
  作者：Francisco Palacios、Itziar Perez de Heredia、Gloria Rubiales

  DOI：10.1016/s0040-4039(00)79357-9

  日期：1993.7

  Di-, tri- and tetra- substituted 2-azadienes 3 underbar with electron withdrawing groups have been obtained by Aza-Wittig reaction of N-vinylic phosphazenes with carbonyl compounds. The Diels-Alder reaction of 3 underbar with trans-cyclooctene has also been explored.
• Synthesis of N-Functionalized Carbodiimides, Hydantoins, 1,3-Diazetidines, and Imidazolidine Derivatives from N-Vinylic Phosphazenes Derived from b-Amino Acids
  作者：Francisco Palacios、Marta Legido、Itziar Pérez de Heredia、José María Ezpeleta、Gloria Rubiales

  DOI：10.3987/com-01-9264

  日期：——

  Synthesis of N-vinylic carbodiimides through Aza-Wittig reaction of N-vinylic phosphazenes with isocyanates is reported. These heterocumulenes are used for the preparation of unsymmetrical ureas and nitrogen heterocycles such as hydantoins, 1,3-diazetidines, imidazolidinones, and bis-imidazolidinone azines.
• Reactivity of Conjugated Phosphazenes Derived from Dehydroaspartic Esters with Acyl Halides. Synthesis of 5(4H)-Oxazolone
  作者：Francisco Palacios、Marta Legido、Itziar Perez de Heredia、Gloria Rubiales

  DOI：10.3987/com-99-s130

  日期：——

  The reactivity of N-vinylic phosphazenes derived from dehydroaspartic esters towards acyl halides is reported. Treatment of conjugated phosphazene with acyl halides led to the formation of N-acylated dehydroaspartic esters and alkenyl-5(4N)-oxazolones. When the reaction was performed in the presence of diethylamine, 1-diethylamino-3,4-dimethoxycarbonyl-2-aza-1,3-butadiene was obtained. Reaction of substituted 5(4H)-oxazolones with water, ethanol and amines gave N-acylated dehydroaspartic acid derivatives.