3,6-bis(4-dimethylaminophenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione | 84632-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3,6-bis(4-dimethylaminophenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione
• 英文别名: 1,4-bis[4-(dimethylamino)phenyl]-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 84632-52-0
• 化学式: C₂₂H₂₂N₄O₂
• 分子量: 374.442
• InChiKey: VWPOPJYOUAKGLH-UHFFFAOYSA-N

物化性质

• 沸点：
  698.9±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.68
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-氯-1-己醇 、 3,6-bis(4-dimethylaminophenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 在 四乙基溴化铵 、 sodium hydride 、 水 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 18.5h， 生成 1,4-Bis[4-(dimethylamino)phenyl]-2,5-bis(6-hydroxyhexyl)pyrrolo[3,4-c]pyrrole-3,6-dione
  参考文献：
  名称：

  [EN] POLYMERISABLE DIKETOPYRROLOPYRROLES, USE OF SUCH COMPOUNDS IN COLOUR FILTERS AND POLYMERS PREPARED FROM THESE COMPOUNDS
  [FR] DICETOPYRROLOPYRROLES POLYMERISABLES, UTILISATION DE CES COMPOSES DANS DES FILTRES COULEURS ET POLYMERES PREPARES A BASE DE CES COMPOSES

  摘要：

  本发明涉及在色彩滤光片中使用可聚合的二酮吡咯吡咯，这些色彩滤光片本身可以用于例如电视屏幕、液晶显示器、电荷耦合器件、等离子显示器或电致发光显示器等电光系统中。与传统颜料相比，可聚合的二酮吡咯吡咯不易聚集，因此具有非常好的分散性。通过使用可聚合的二酮吡咯吡咯制备的色彩滤光片具有高透明度和纯净的色调。此外，它们有助于调整颜色点并提供大量的色调选择。

  公开号：

  WO2004009710A1
• 作为产物：
  描述：

  丁二酸二异丙酯 、 4-(二甲胺基)苄腈 在 iron(III) chloride 、 sodium 、 水 作用下， 以 2-甲基-2-丁醇 为溶剂， 以10%的产率得到3,6-bis(4-dimethylaminophenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione
  参考文献：
  名称：

  Novel, soluble diphenyl-diketo-pyrrolopyrroles: Experimental and theoretical study

  摘要：

  Derivatives of diphenyl-diketo-pyrrolopyrrole, possessing electron-donating or withdrawing groups in the p-position of the phenyl, were synthesized and studied using optical characterization (absorption, fluorescence, time-resolved fluorescence) and quantum chemical calculation. An increase in absorption coefficient >= 10(5) dm(3) mol(-1) cm(-1) was observed using electron-donor groups; a bathochromic shift in both absorption and luminescence peaks was observed as a result of increased conjugation. Soluble derivatives were obtained by the introduction of alkyl groups (by N-alkylation) in the central pyrrolopyrrole unit. Calculated phenyl torsion angles using HF and B3LYP methods showed that the loss of molecule planarity reduced the extent of overlap between the pi-orbitals of the central pyrrolopyrrole unit and phenyls after N-alkylation. This treatment thus reduced both the bathochromic shift and increased absorption coefficient. The presence of the donor or acceptor groups in itself does not influence molecule planarity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.07.014

文献信息

• Fluorescent diketopyrrolopyrroles
  申请人：——

  公开号：US20030187106A1

  公开（公告）日：2003-10-02

  Fluorescent diketopyrrolopyrroles (“DPPs”) of the formula I 1 wherein R 1 and R 2 , independently from each other, stand for C 1 -C 25 -alkyl, allyl which can be substituted one to three times with C 1 -C 3 alkyl or Ar 3 , —CR 3 R 4 —(CH 2 ) m —Ar 3 , wherein R 3 and R 4 independently from each other stand for hydrogen or C 1 -C 4 alkyl, or phenyl which can be substituted on to three times with C 1 -C 3 alkyl, Ar 3 stands for phenyl or 1- or 2-naphthyl which can be substituted one to three times with C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen or phenyl, which can be substituted with C 1 -C 8 alkyl or C 1 -C 8 alkoxy one to three times, and m stands for 0, 1, 2, 3 or 4, and wherein C 1 -C 25 -alkyl or —CR 3 R 4 —(CH 2 ) m —Ar 3 , preferably C 1 -C 25 -alkyl, can be substituted with a functional group capable of increasing the solubility in water such as a tertiary amino group, —SO 3 − , or PO 4 2− , Ar 1 , and Ar 2 , independently from each other, stand for 2 wherein R 5 stands for C 1 -C 6 alkyl, —NR 8 R 9 , —OR 10 , —S(O) n R 8 , —Se(O) n R 8 , or phenyl, which can be substituted one to three times with C 1 -C 8 alkyl or C 1 -C 8 alkoxy, wherein R 8 and R 9 , independently from each other, stand for hydrogen, C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, —CR 3 R 4 —(CH 2 ) m —Ph, R 10 , wherein R 10 stands for C 6 -C 24 -aryl, or a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein Ph, the aryl and heterocyclic radical can be substituted one to three times with C 1 -C 8 alkyl, C 1 -C 8 alkoxy, or halogen, or R 8 and R 9 stand for —C(O)R 10 , wherein R 11 can be C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, R 10 , —OR 12 or —NR 13 R 14 , wherein R 12 , R 13 , and R 14 stand for C 1 -C 25 -alkyl, C 5 -C 12 -cycloalkyl, C 6 -C 24 -aryl, or a saturated or unsaturated heterocyclic radical comprising five to seven ring atoms, wherein the ring consists of carbon atoms and one to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the aryl and heterocyclic radical can be substituted one to three times with C 1 -C 8 alkyl or C 1 -C 8 alkoxy, or —NR 8 R 9 stands for a five- or sixmembered heterocyclic radical in which R 8 and R 9 together stand for tetramethylene, pentamethylene, —CH 2 —CH 2 —O—CH 2 —CH 2 —, or —CH 2 —CH 2 —NR 5 —CH 2 —CH 2 —, preferably —CH 2 —CH 2 —O—CH 2 —CH 2 —, and n stands for 0, 1, 2 or 3, and wherein R 6 and R 7 , independently from each other, stand for hydrogen or R 5 , but do not stand simultaneously for hydrogen, processes for its preparation, its uses and compositions comprising the compounds I.

  荧光二酮吡咯烷酮（“DPPs”）的公式I1，其中R1和R2，独立地代表C1-C25烷基，可以用C1-C3烷基或Ar3取代的丙烯基，—CR3R4—（CH2）m—Ar3，其中R3和R4独立地代表氢或C1-C4烷基，或苯基，可以用C1-C3烷基取代，Ar3代表苯基或1-或2-萘基，可以用C1-C8烷基，C1-C8烷氧基，卤素或苯基取代一至三次，m代表0、1、2、3或4，其中C1-C25烷基或—CR3R4—（CH2）m—Ar3，优选为C1-C25烷基，可以用增加水溶性的功能基团取代，例如三级胺基，—SO3−或PO42−，Ar1和Ar2独立地代表2，其中R5代表C1-C6烷基，—NR8R9，—OR10，—S（O）nR8，—Se（O）nR8或苯基，可以用C1-C8烷基或C1-C8烷氧基取代一至三次，其中R8和R9独立地代表氢，C1-C25烷基，C5-C12环烷基，—CR3R4—（CH2）m—Ph，其中R10代表C6-C24芳基，或由五至七个环原子组成的饱和或不饱和杂环基团，其中环由碳原子和从氮、氧和硫中选择的一至三个杂原子组成，其中Ph，芳基和杂环基团可以用C1-C8烷基，C1-C8烷氧基或卤素取代一至三次，或R8和R9代表—C（O）R10，其中R11可以是C1-C25烷基，C5-C12环烷基，R10，—OR12或—NR13R14，其中R12、R13和R14代表C1-C25烷基，C5-C12环烷基，C6-C24芳基，或由五至七个环原子组成的饱和或不饱和杂环基团，其中环由碳原子和从氮、氧和硫中选择的一至三个杂原子组成，其中芳基和杂环基团可以用C1-C8烷基或C1-C8烷氧基取代一至三次，或—NR8R9代表一个五元或六元杂环基团，其中R8和R9一起代表四亚甲基，五亚甲基，—CH2—CH2—O—CH2—CH2—或—CH2—CH2—NR5—CH2—CH2—，优选为—CH2—CH2—O—CH2—CH2—，n代表0、1、2或3，其中R6和R7独立地代表氢或R5，但不同时代表氢，其制备方法，其用途和包含化合物I的组合物。
• Cationic pyrrolo-pyrrol-derivatives, method for producing them and colorants for keratin fibres, containing these compounds
  申请人：——

  公开号：US20030055268A1

  公开（公告）日：2003-03-20

  The object of the present invention are diketopyrrolopyrroles of the general formula (I) 1 wherein, independently of one another, Q 1 and Q 2 represent an optionally substituted, aromatic, isocyclic or heterocyclic group with 5 to 14 atoms in the ring, the heterocyclic group containing at least one oxygen, nitrogen or sulfur atom, and the R1 and R2 groups, independently of one another represent hydrogen or a Y—B + A − group, with the proviso that at least one of the R1 and R2 groups is not hydrogen; B + is an aromatic, aliphatic, alicyclic, aromatic heterocyclic or non-aromatic heterocyclic, quaternary ammonium group or a quaternary phosphonium group; Y is an optionally substituted linear or branched C 1 to C 6 alkylcne group and A − is an anion; a method for their synthesis as well as agents, containing compounds of formula (I), for dyeing keratin fibers.

  本发明的目的是通式(I)的二酮吡咯并吡咯化合物 1 其中，Q 1 和 Q 2 代表环中含有 5 至 14 个原子的任选取代的芳香族、异环或杂环基团，杂环基团含有至少一个氧原子、氮原子或硫原子，且 R1 和 R2 基团各自代表氢或 Y-B 和加合物； A - 基团，但 R1 和 R2 基团中至少有一个不是氢；B 加 是芳香族、脂肪族、脂环族、芳香杂环族或非芳香杂环族、季铵基团或季鏻基团；Y 是任选取代的线性或支链 C 1 至 C 6 烷基和 A - 是阴离子；其合成方法以及含有式 (I) 化合物的染色剂，用于染色角蛋白纤维。
• Electroluminescent devices comprising diketopyrrolopyrroles
  申请人：Ciba Specialty Chemicals Holding Inc.

  公开号：EP1087006B1

  公开（公告）日：2003-10-15
• KATIONISCHE PYRROLO-PYRROL-DERIVATE, VERFAHREN ZU DEREN HERSTELLUNG UND DIESE VERBINDUNGEN ENTHALTENDE FÄRBEMITTEL FÜR KERATINFASERN
  申请人：Wella Aktiengesellschaft

  公开号：EP1185531A1

  公开（公告）日：2002-03-13
• POLYMERISABLE DIKETOPYRROLOPYRROLES, USE OF SUCH COMPOUNDS IN COLOUR FILTERS AND POLYMERS PREPARED FROM THESE COMPOUNDS
  申请人：BASF SE

  公开号：EP1523528B1

  公开（公告）日：2012-02-22