1-diphenylmethyleneamino-5-methoxycarbonyl-4-p-toluoyl-2,3-dihydro-2,3-pyrroledione | 409343-66-4

• 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-diphenylmethyleneamino-5-methoxycarbonyl-4-p-toluoyl-2,3-dihydro-2,3-pyrroledione
• 英文别名: methyl 1-diphenylmethyleneamino-3-p-toluoyl-4,5-dihydro-4,5-dioxo-1H-pyrrole-2-carboxylate；5-methoxycarbonyl-1-diphenylmethyleneamino-4-p-toluoyl-2,3-dihydro-2,3-pyrroledione；methyl 1-(benzhydrylideneamino)-3-(4-methylbenzoyl)-4,5-dioxopyrrole-2-carboxylate
• CAS: 409343-66-4
• 化学式: C₂₇H₂₀N₂O₅
• 分子量: 452.466
• InChiKey: YWOYVRHCMDAANB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  93.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-diphenylmethyleneamino-5-methoxycarbonyl-4-p-toluoyl-2,3-dihydro-2,3-pyrroledione 在 水 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以25%的产率得到methyl 1-diphenylmethyleneamino-2,4-dihydroxy-3-p-toluoyl-2,5-dihydro-5-oxo-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  （N-亚甲基氨基）亚胺基乙烯酮的稳定化：双吡唑并[1,2- a ; 1'，2'- d ] [1,2,4,5]四嗪的合成

  摘要：

  取代的甲基1-亚甲基氨基-4,5-二氧代-4,5-二氢-1 H-吡咯-2-羧酸酯2a，b的热解反应生成取代的二甲基3,9-二氧代-1,5,7,11-四氢甲基-1 H，7 H -dipyrazolo [1,2- a ; 1'，2'- d ] [1,2,4,5]四嗪-1,7-二羧酸盐4a，b和甲基2,5-二氢-作为次要产物的5-氧代-1 H-吡唑-3-羧酸酯5a，b。化合物4a的结构通过X射线晶体学确定。提议的这种转换机制包括生成（N-亚甲基氨基）亚氨基基乙烯酮6a，b及其分子内转化为偶氮甲亚胺-5-氧代-2,5-二氢吡唑-1-甲基-2-化物7a，b，它们以头尾相接的方式进行二聚，得到产物4a，b b并部分水解为化合物5a，b。

  DOI：

  10.1016/j.tet.2004.04.080
• 作为产物：
  描述：

  4-(4-甲基苯基)-2,4-二氧代丁酸甲酯 在 溶剂黄146 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 3.5h， 生成 1-diphenylmethyleneamino-5-methoxycarbonyl-4-p-toluoyl-2,3-dihydro-2,3-pyrroledione
  参考文献：
  名称：

  用于[4 + 2]和[4 +1]偶极杂环加成反应的原位生成烯醇盐-亚胺基1,4-偶极的 新方法†

  摘要：

  通过N-（二苯基烯氨基）吡咯二酮的热分解生成烯基酮与5 -exo-trig闭环一起提供两性离子二氢吡唑酮类。与Lisowskaya的早期报告相反，我们确定在大多数环加成反应中，此类二氢吡唑并酮以1,4-偶极的形式发生反应。在几种[4 + 4]同二聚化反应以及一系列[4 + 2]和[4 +1]与各种偶极亲子的环加成反应中，证明了这种反应模式。

  DOI：

  10.1039/c6ra21981k

文献信息

• Dipyrazolodioxadiazocines as shelf-stable “ready-to-use” precursors for an <i>in situ</i> generation of enolate-iminium 1,4-dipoles: a straightforward atom-economical approach to pyrazolo[5,1-<i>d</i>][1,3,5]dioxazines
  作者：Vladimir E. Zhulanov、Valeria A. Vigovskaya、Maksim V. Dmitriev、Pavel S. Silaichev、Andrey N. Maslivets、Michael Rubin

  DOI：10.1039/d0ob00451k

  日期：——

  Generation of cyclic enolate-iminium 1,4-dipoles via thermolysis of dipyrazolodioxadiazocines in the presence of ketones allowed for efficient preparation of pyrazolo[5,1-d][1,3,5]dioxazines.

  通过在酮的存在下热解二吡唑二氧杂二氮环生成环状烯醇酮-亚胺1,4-二极分子，有效地制备了吡唑并[5,1-d][1,3,5]二氧杂嘧啶。
• Thermolysis of 1-(methylideneamino)-1H-pyrrole-2,3-diones. Synthesis of pyrazolooxazines by [4 + 2]-cycloaddition of azomethine imines to alkenes
  作者：V. E. Zhulanov、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428017100086

  日期：2017.10

  Thermolysis of methyl 3-acyl-1-[(diphenylmethylidene)amino]-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates generates 4-acyl-1-(diphenylmethylidene)-3-(methoxycarbonyl)-1H-pyrazol-1-ium-5-olates which react with alkenes to give methyl 3-acyl-7,7-diphenyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2- carboxylates. The product structure was confirmed by X-ray analysis.

  3-酰基-1-[[（二苯甲基亚甲基）氨基] -4,5-二氧代-4,5-二氢-1 H-吡咯-2-羧酸甲酯的热解生成4-酰基-1-（二苯基亚甲基）-3-（甲氧基羰基）-1 H-吡唑-1-鎓-5-酸酯与烯烃反应生成甲基3-酰基-7,7-二苯基-6,7-二氢-5 H-吡唑并[5,1- b ] [ 1,3]恶嗪-2-羧酸盐。通过X射线分析确认了产物结构。
• ——
  作者：N. A. Konykhova、O. P. Krasnykh、A. N. Maslivets

  DOI：10.1023/a:1011625126078

  日期：——
• ——
  作者：Z. G. Aliev、O. P. Krasnykh、N. A. Konyukhova、A. N. Maslivets、L. O. Atovmyan

  DOI：10.1023/a:1017942005554

  日期：——

  The reaction between methyl 2-diphenylmethylenehydrazino-4-oxo-4-p-tolyl-2-butenic ether and oxalyl chloride gave 1-diphenylmethyleneamino-5-methoxycarbonyl-4-p-toluoyl-2,3-dihydro-2,3-pyrroledione, which adds water to yield substituted 3,5-dihydroxy-2,5-dihydro-2-pyrrolone. The crystal and molecular structure of pyrrolone and the inter- and intramolecular hydrogen bonds in its crystals and solutions were investigated by IR spectroscopy and XRD analysis. The crystals of C27H22N2O6 are triclinic with cell dimensions a = 9.8540(10), b = 10.0880(10), c = 13.982(2) Angstrom, alpha = 69.820(10), beta = 110.57(10), gamma = 91.350(10)degrees, V = 1213.8(2) Angstrom(3), M = 470.47, d(calc) = 1.287 g/cm(3), Z = 2, space group P (1) over bar. The data were collected on a KM-4 (KUMA DIFFRACTION) diffractometer, 3781 reflections with I greater than or equal to 2sigma(I). Direct methods, hydrogen atoms localized, least squares refinement (in an anisotropic approximation for non-hydrogen atoms), R = 0.0454. The crystal is built from the centrosymmetric dimer associates of molecules bonded by strong (2.64 Angstrom) intermolecular hydrogen bonds (IMHB) of O-H...O type. The dimer associates are linked by weaker (2.82 Angstrom) centrosymmetric IMHB, forming an infinite chain of hydrogen-bonded molecules.
• Thermolysis of 1-(methylideneamino)-1H-pyrrole-2,3-diones. Formation of pyrazolodioxazines at [4+2]-cycloaddition of azomethinimines to arylcarbaldehydes
  作者：V. E. Zhulanov、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s107042801705013x

  日期：2017.5

  4-Acyl-1-[(diphenylmethylidene)amino]-5-methoxycarbonyl-1De-pyrrole-2,3-diones generate at the thermolysis 4-acyl-3-(methoxycarbonyl)-1-(diphenylmethylidene)-1H-pyrazol-1-ium-5-olates that react with aromatic aldehydes to form methyl 2-aryl-8-acyl-4,4-diphenyl-4H-pyrazolo[5,1-d][1,3,5]dioxazine-7-carboxylates whose structure is proved by X-ray diffraction analysis.