3-苯胺基-4-氯-1-苯基吡咯-2,5-二酮 | 6903-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 3-苯胺基-4-氯-1-苯基吡咯-2,5-二酮
• 英文名称: 3-Chlor-1-phenyl-4-phenylamino-pyrrolin-2,5-dion
• 英文别名: 3-anilino-4-chloro-1-phenyl-pyrrole-2,5-dione；3-Anilino-4-chlor-1-phenyl-pyrrol-2,5-dion；1-Phenyl-3-phenylamino-4-chlor-3,4-pyrrolin-2,5-dion；1-Anilino-2-chlor-n-phenyl-maleinsaeure-imid；2-Chlor-3-anilino-maleinsaeure-N-phenylimid；2-Anilino-3-chlor-N-phenyl-maleinimid；3-Anilino-4-chloro-1-phenylpyrrole-2,5-dione
• CAS: 6903-92-0
• 化学式: C₁₆H₁₁ClN₂O₂
• 分子量: 298.729
• InChiKey: IJYHJPUCQKQUMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-苯胺基-4-氯-1-苯基吡咯-2,5-二酮 在 ammonium hydroxide 、 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成 3-Phenylcarbamoyl-quinoxaline-2-carboxylic acid; compound with ammonia
  参考文献：
  名称：

  合成von chinoxalin-和indol-2,3-dicarbonsäureimiden

  摘要：

  喹喔啉和吲哚-2，3-二羧酸酰亚胺7、8是通过使卤化马来酰亚胺1、2与叠氮化钠反应而制备的。这些杂环系列的其他衍生物可通过酰亚胺的二次反应获得。

  DOI：

  10.1016/0040-4020(80)80077-9
• 作为产物：
  描述：

  N-苯基马来酰亚胺 在 吡啶 、 氯化亚砜 作用下， 生成 3-苯胺基-4-氯-1-苯基吡咯-2,5-二酮
  参考文献：
  名称：

  Luu-Duc; Marsura; Charlon, Farmaco, Edizione Scientifica, 1985, vol. 40, # 4, p. 253 - 258

  摘要：

  DOI：

文献信息

• Asymmetrische katalyse
  作者：Annegret Tillack、Manfred Michalik、Dieter Fenske、Helmut Goesmann

  DOI：10.1016/0022-328x(94)88188-x

  日期：1994.11

  no-4-phenylamino-pyrrolin-2,5-dion (12) has been determined by X-ray crystallography. The pyrrolin-2,5-diones have been applied as planar, chiral N,N-ligands to modify the [Rh(COD)Cl]2 catalyst in the asymmetric hydrosilylation reaction of acetophenone. However, the optical induction observed for this reaction are poor for N,N-ligands as compared to the corresponding P,P-ligands.

  二氯马来酰亚胺与光学活性胺的反应得到手性吡咯啉-2，5-二酮。二胺通过13 C-NMR光谱表征。另外，通过X射线晶体学测定了1-（R）-薄荷基-3-（R）-薄荷基氨基-4-苯基氨基-吡咯啉-2，5-dion（12）的分子结构。吡咯啉2,5-二酮已被用作平面手性N，N配体，以修饰苯乙酮的不对称氢化硅烷化反应中的[Rh（COD）Cl] 2催化剂。然而，与相应的P，P-配体相比，对于该反应，观察到的N，N-配体的光感应差。
• Syntheses and structures of N-phenylmaleimidetriazoles and by-products
  作者：Yingqun Mao、Iain Maley、William H. Watson

  DOI：10.1007/s10870-005-1693-y

  日期：2005.5

  The syntheses, properties, and structures of N-phenylmaleimidetriazole derivatives are described. Intermediates and by-products are also discussed. 1b. a = 43.997(7) Å, 5.7610(9) Å, 8.245(1) Å, β = 99.339(4)∘, C2/c; 2a. a = 13.646(4) Å, b = 7.744(2) Å, c = 10.612(3) Å, β = 91.979(6)∘, P21/c. 3a. a = 22.245(1) Å, b = 22.245(1) Å, 10.010(1) Å, P42/n. 3a′. a = 11.727(2) Å, b = 14.075(3) Å, c = 16.080(3) Å, α = 105.859(3)∘, β = 105.331(3)∘, γ = 98.187(3)∘, P-1. 3b. a = 8.561(3) Å, b = 14.755(5) Å, c = 22.771(7) Å, β = 97.006(5)∘, P21/c. 3c. a = 10.500(2) Å, b = 12.189(2) Å, c = 13.040(2) Å, α = 109.091(3)∘, β = 106.089(3)∘, γ = 101.022(3)∘, P-1. 8a. a = 16.389(8) Å, b = 5.749(3) Å, c = 19.316(3) Å, β = 97.467(9)∘, P21/n. 8b. a = 5.822(2) Å, b = 10.114(3) Å, c = 16.705(4) Å, α = 84.681(5)∘, β = 82.840(5)∘, γ = 75.769(4)∘, P-1. 9b. a = 11.251(1) Å, 13.335(3) Å, 13.376(3) Å, β = 102.456(4)∘, P21/n. 9c. a = 15.836(3) Å, b = 8.236(2) Å, c = 5.447(3) Å, β = 92.551(3)∘, P21/c. 10a. a = 13.177(2) Å, b = 14.597(2) Å, c = 5.5505(8) Å, β = 110.979(2)∘, Cc. 11a. a = 14.720(2) Å, b = 13.995(2) Å, c = 38.245(6) Å, β = 94.430(3)∘, P21/n. 12b. a = 15.067(5) Å, b = 20.378(6) Å, c = 8.669(5) Å, α = 99.16(4)∘, β = 99.32(3)∘, γ = 105.23(3)∘, P-1. 13b. a = 8.2824(6) Å, b = 10.5245(7) Å, c = 15.518(1) Å, α = 92.305(1)∘, β = 100.473(1)∘, γ = 100.124(1)∘, P-1. 15a. a = 15.357(3) Å, b = 7.778(2) Å, c = 22.957(2) Å, Pbca. 16b. a = 18.0384(4) Å, b = 12.474(3) Å, c = 20.078(5) Å, Pbca.

  N-苯基马来酰亚胺三唑衍生物的合成、性质和结构进行了描述。还讨论了中间体和副产品。1b. a = 43.997(7) Å，5.7610(9) Å，8.245(1) Å，β = 99.339(4)°，C2/c；2a. a = 13.646(4) Å，b = 7.744(2) Å，c = 10.612(3) Å，β = 91.979(6)°，P21/c。3a. a = 22.245(1) Å，b = 22.245(1) Å，10.010(1) Å，P42/n。3a′. a = 11.727(2) Å，b = 14.075(3) Å，c = 16.080(3) Å，α = 105.859(3)°，β = 105.331(3)°，γ = 98.187(3)°，P-1。3b. a = 8.561(3) Å，b = 14.755(5) Å，c = 22.771(7) Å，β = 97.006(5)°，P21/c。3c. a = 10.500(2) Å，b = 12.189(2) Å，c = 13.040(2) Å，α = 109.091(3)°，β = 106.089(3)°，γ = 101.022(3)°，P-1。8a. a = 16.389(8) Å，b = 5.749(3) Å，c = 19.316(3) Å，β = 97.467(9)°，P21/n。8b. a = 5.822(2) Å，b = 10.114(3) Å，c = 16.705(4) Å，α = 84.681(5)°，β = 82.840(5)°，γ = 75.769(4)°，P-1。9b. a = 11.251(1) Å，13.335(3) Å，13.376(3) Å，β = 102.456(4)°，P21/n。9c. a = 15.836(3) Å，b = 8.236(2) Å，c = 5.447(3) Å，β = 92.551(3)°，P21/c。10a. a = 13.177(2) Å，b = 14.597(2) Å，c = 5.5505(8) Å，β = 110.979(2)°，Cc。11a. a = 14.720(2) Å，b = 13.995(2) Å，c = 38.245(6) Å，β = 94.430(3)°，P21/n。12b. a = 15.067(5) Å，b = 20.378(6) Å，c = 8.669(5) Å，α = 99.16(4)°，β = 99.32(3)°，γ = 105.23(3)°，P-1。13b. a = 8.2824(6) Å，b = 10.5245(7) Å，c = 15.518(1) Å，α = 92.305(1)°，β = 100.473(1)°，γ = 100.124(1)°，P-1。15a. a = 15.357(3) Å，b = 7.778(2) Å，c = 22.957(2) Å，Pbca。16b. a = 18.0384(4) Å，b = 12.474(3) Å，c = 20.078(5) Å，Pbca。
• Anschuetz; Beavis, Justus Liebigs Annalen der Chemie, 1897, vol. 295, p. 32
  作者：Anschuetz、Beavis

  DOI：——

  日期：——
• Salmony; Simonis, Chemische Berichte, 1905, vol. 38, p. 2594
  作者：Salmony、Simonis

  DOI：——

  日期：——
• Some synthetic applications of 2,3-Dichloro-N-phenylmaleimide: A novel synthesis of 2-phenylpyrrolo[3,4-b]quinoxaline-1,3-diones. I
  作者：Leila Hanaineh-Abdelnour、Shibly Bayyuk、Rima Theodorie

  DOI：10.1016/s0040-4020(99)00672-9

  日期：1999.10

  2,3-Dichloro-N-phenylmaleimide 2 undergoes nucleophilic substitution reactions by a variety of nucleophiles giving either monosubstituted 5 or disubstituted 3 products. Treatment of 5 with sodium azide at room temperature results in cyclization to the corresponding 2-phenylpyrrolo[3,4-b]quinoxaline-1,3-diones 6, while at higher temperatures 5 is reduced to the 2-amino-3-amino-N-phenylmaleimides 7. (C) 1999 Elsevier Science Ltd. All rights reserved.