N,N'-diacetyl-N,N'-diphenyl-1,4-phenylenediamine | 113510-51-3

• 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: N,N'-diacetyl-N,N'-diphenyl-1,4-phenylenediamine
• 英文别名: N-[4-(N-acetylanilino)phenyl]-N-phenylacetamide
• CAS: 113510-51-3
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: ZOPJMPGWPDKRID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-diacetyl-N,N'-diphenyl-1,4-phenylenediamine 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.5h， 以1.55 g的产率得到N,N'-二苯基-1,4-苯二胺
  参考文献：
  名称：

  乙酸钯 (II) 和紫外光对异构 N,N'-二苯二胺及其 N,N'-二甲基衍生物的氧化环化作用

  摘要：

  摘要 N,N'-二苯基-邻-、间-和对苯二胺及其 N,N'-二甲基衍生物在乙酸钯 (II) 和紫外光下的环化分别导致双环化，提供吲哚并咔唑和单环化与裂解以及一个取代基的保留，产生取代的咔唑。

  DOI：

  10.1080/00397910008086992
• 作为产物：
  描述：

  对苯二胺 在 吡啶 、 copper (I) iodide 、 potassium carbonate 作用下， 反应 25.0h， 生成 N,N'-diacetyl-N,N'-diphenyl-1,4-phenylenediamine
  参考文献：
  名称：

  乙酸钯 (II) 和紫外光对异构 N,N'-二苯二胺及其 N,N'-二甲基衍生物的氧化环化作用

  摘要：

  摘要 N,N'-二苯基-邻-、间-和对苯二胺及其 N,N'-二甲基衍生物在乙酸钯 (II) 和紫外光下的环化分别导致双环化，提供吲哚并咔唑和单环化与裂解以及一个取代基的保留，产生取代的咔唑。

  DOI：

  10.1080/00397910008086992

文献信息

• Preparation and properties of two-legged ladder polymers based on polydiacetylenes
  作者：Hideyuki Tabata、Hiroaki Tokoyama、Hideo Yamakado、Tsunehisa Okuno

  DOI：10.1039/c1jm13896k

  日期：——

  A novel diacetylene derivative, N,N′-bis[5-(3-tolylaminocarbonyloxy)-1,3-pentadiynyl]-N,N′-diphenyl-1,4-phenylenediamine (1), was prepared, where two diacetylene groups were connected by a 1,4-phenylenediamine moiety. The molecules stacked one-dimensionally and showed solid-state-polymerization reactivity above 80 °C. The decay of the monomers at 100 °C proceeded gradually without a marked induction period and was fully completed after 400 h. The obtained polymer was a crystalline solid judged by powder X-ray diffraction (PXRD) patterns and SEM imaging. The conjugated π-system of the obtained polymer was classified as a two-legged conjugated ladder. The polymer showed a broad absorption from the visible to the near IR region, indicating a decrease in the optical band gap of ca. 1.0 eV, because of the expansion of the π-conjugated system from a one-dimensional system to a ladder. The ladder polymer showed high conductivity after I2 doping from σ293K = 5 × 10−12 S cm−1 to 1.2 × 10−5 S cm−1. The conductivity depended heavily on the pressure of iodine and reached σ373K = 2.3 × 10−1 S cm−1. The activation energy of the ladder polymer was also estimated as 360 meV.

  制备了一种新型二乙炔衍生物 N,N′-双[5-（3-甲苯胺基羰基氧基）-1,3-戊二炔基]-N,N′-二苯基-1,4-苯二胺（1），其中两个二乙炔基团由一个 1,4- 苯二胺分子连接。分子呈一维堆积，在 80 °C 以上显示出固态聚合反应活性。根据粉末 X 射线衍射（PXRD）图样和扫描电镜成像判断，获得的聚合物为结晶固体。所得聚合物的共轭 π 系统被归类为两脚共轭梯形结构。由于π共轭体系从一维体系扩展为梯形，该聚合物显示出从可见光到近红外区域的宽吸收，表明光带隙下降了约 1.0 eV。掺入 I2 后，梯形聚合物显示出很高的导电性，从 σ293K = 5 × 10-12 S cm-1 到 1.2 × 10-5 S cm-1。电导率在很大程度上取决于碘的压力，达到了 σ373K = 2.3 × 10-1 S cm-1。梯形聚合物的活化能估计为 360 meV。
• Calm, Chemische Berichte, 1883, vol. 16, p. 2799
  作者：Calm

  DOI：——

  日期：——
• A Simple Route to <i>N-</i>Arylated 2-Aminothiophenes as a New Class of Amorphous Glass Forming Molecules
  作者：Horst Hartmann、Peter Gerstner、Dirk Rohde

  DOI：10.1021/ol015875c

  日期：2001.5.1

  [GRAPHICS]By thermal decarboxylation of N-arylated 2-aminothiophene-5-cacrboxylates, a versatile, heavy-metal free method for preparing the title compounds as new class of highly reactive and easily oxidable, amorphous glass forming molecules has been elaborated.
• One-Pot Synthesis of Helical Aromatics:  Stereoselectivity, Stability against Racemization, and Assignment of Absolute Configuration Assisted by Experimental and Theoretical Circular Dichroism
  作者：Masashi Watanabe、Hiroshi Suzuki、Yasutaka Tanaka、Toshimasa Ishida、Tatsuo Oshikawa、Akiyoshi Tori-i

  DOI：10.1021/jo048858k

  日期：2004.11.1

  Helical aromatics (1) were synthesized via one step in good quantity by solvent-free condensation of NY-p-phenylenediamine (2) and various carboxylic acids in the presence of a Lewis acid. Microwave irradiation greatly facilitated the condensation reaction to furnish 1 with a 100% diastereo- and a 50% enantioselectivity, when a chiral carboxylic acid was utilized. If, derived from 2-methylglutaric acid, was quite stable, no racemization taking place even at 200 degreesC. The assignment of the absolute configurations to the helical aromatics has been achieved by experimental and theoretical CD spectra calculated by time-dependent density functional theory.
• Lopez-Alvarado, Pilar; Avendano, Carmen; Grande, Mercedes T., Heterocycles, 1990, vol. 31, # 11, p. 1983 - 1996
  作者：Lopez-Alvarado, Pilar、Avendano, Carmen、Grande, Mercedes T.、Menendez, J. Carlos

  DOI：——

  日期：——