1,6-bis(1-naphthyl)-2,5-diazahexa-1,5-diene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,6-bis(1-naphthyl)-2,5-diazahexa-1,5-diene
• 英文别名: N~1~,N~2~-Bis(1-naphthylmethylene)-1,2-ethanediamine；1-naphthalen-1-yl-N-[2-(naphthalen-1-ylmethylideneamino)ethyl]methanimine
• 化学式: C₂₄H₂₀N₂
• 分子量: 336.436
• InChiKey: HEDFJWUXBLLAKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-bis(1-naphthyl)-2,5-diazahexa-1,5-diene 在 titanium(IV) isopropylate 、 四氯化钛 、 三乙胺 、 O,O'-dibenzoyl-L-tartaric acid 、 potassium iodide 、 锌 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 32.0h， 生成 (2S,3S)-2,3-di(naphthalen-1-yl)-1,4-diazabicyclo[2.2.2]octane
  参考文献：
  名称：

  手性2,3-二取代的1,4-二氮杂双环[2.2.2]辛烷衍生物的合成

  摘要：

  外消旋的2,3-二芳基-1,4-二氮杂双环[2.2.2]辛烷（DABCO）衍生物是由易于获得的哌嗪在80°C的条件下通过环化反应使用溴化乙烯，三乙胺和KI合成的，收率为50-64％。对映体富集的2,3-二苯基哌嗪和2,3-双（1-萘基）哌嗪衍生物是通过拆分方法使用市售的旋光酸制备的，相应的DABCO衍生物的收率为51-64％，最高可达99％ ％ee。这种温和的环化作用也可用于对映体纯的樟脑二胺衍生物，且产品收率为72–86％。

  DOI：

  10.1021/jo502688b
• 作为产物：
  描述：

  1-萘甲醛 、 乙二胺 以 乙醇 为溶剂， 反应 36.0h， 以78%的产率得到1,6-bis(1-naphthyl)-2,5-diazahexa-1,5-diene
  参考文献：
  名称：

  Hg(II)-Selective Excimer Emission of a Bisnaphthyl Azadiene Derivative

  摘要：

  [GRAPHICS]A bisnaphthyl azadiene derivative (L) demonstrates Hg2+-selective intermolecular excimer emission. This emission is responsive to the number of coordinated Hg2+ atoms, where 2 : 2 and 2 : 3 L-Hg2+ complexes are the strongly emissive components, whereas the 2 : 1 complex is nonemissive.

  DOI：

  10.1021/ol0713133

文献信息

• Discovery of chiral catalysts by asymmetric activation for highly enantioselective diethylzinc addition to imines: using racemic and achiral diimines as effective activators
  作者：Hua Liu、Hai-Le Zhang、Shuang-Jun Wang、Ai-Qiao Mi、Yao-Zhong Jiang、Liu-Zhu Gong

  DOI：10.1016/j.tetasy.2005.07.014

  日期：2005.9

  A library of chiral zinc complexes formed in Situ by the combination of achiral and racemic diimines with 3,3'-di(3,5-ditrifluoromethylphenyl)-BINOL and diethylzinc were evaluated in the asymmetric addition of diethylzine to N-acylimines. In the presence of 10 mol % of chiral ligand 4 and racemic diimine 5, high enantioselectivities of up to 97% ee and yields of up to 96% were achieved for a wide range of aromatic imines in dichloromethane at -30 degrees C. (c) 2005 Elsevier Ltd. All rights reserved.
• Melo, J. Seixas de; Albelda, M. Teresa; Diaz, Pilar, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 5, p. 991 - 998
  作者：Melo, J. Seixas de、Albelda, M. Teresa、Diaz, Pilar、Garcia-Espana, Enrique、Lodeiro, Carlos、Alves, Sergio、Lima, Joao C.、Pina, Fernando、Soriano, Conxa

  DOI：——

  日期：——
• Sequential Staudinger Ketene−Imine Cycloaddition, RCM Approach to Highly Rigid Macrocrocyclic Bisazetidinones
  作者：Yehia A. Ibrahim、Talal F. Al-Azemi、Mohamed D. Abd El-Halim

  DOI：10.1021/jo100679d

  日期：2010.7.2

  An efficient approach to highly rigid macrocyclic bisazetidinones with interesting structural feature was achieved via sequential Staudinger ketene-imine cycloaddition of o-allyloxyphenoxyketene and bis-arylidenediamines followed by RCM. The ketene-imine cycloaddition afforded the corresponding bis-o-allyloxyphenoxyazetidinones as the cis-cis diastereomers, exclusively obtained as a mixture of cis-syn-cis and cis-anti-cis. RCM of the latter using Grubbs' catalysts afforded good yields of the corresponding novel macrocyclic bisazetidinones. The cis-anti-cis bisazetidinones are readily identified by (1)H NMR using Eu(hfc)(3) chiral shift reagent. (1)H NMR indicated the high shielding effect of the aryl substituents on one of the ortho-H's of the condensed phenylene ring, and VT (1)H NMR indicates the highly restricted rotation of the aryl groups, thus offering a highly rigid system.
• Synthesis of Chiral 2,3-Disubstituted 1,4-Diazabicyclo[2.2.2]octane Derivatives
  作者：Mariappan Periasamy、Athukuri Edukondalu、Polimera Obula Reddy

  DOI：10.1021/jo502688b

  日期：2015.4.3

  Racemic 2,3-diaryl-1,4-diazabicyclo[2.2.2]octane (DABCO) derivatives are synthesized from the readily accessible piperazines in 50–64% yield by cyclization using ethylene bromide, triethylamine, and KI at 80 °C. The enantiomerically enriched 2,3-diphenylpiperazine and the 2,3-bis(1-naphthyl)piperazine derivatives are prepared by a resolution method using commercially available optically active acids

  外消旋的2,3-二芳基-1,4-二氮杂双环[2.2.2]辛烷（DABCO）衍生物是由易于获得的哌嗪在80°C的条件下通过环化反应使用溴化乙烯，三乙胺和KI合成的，收率为50-64％。对映体富集的2,3-二苯基哌嗪和2,3-双（1-萘基）哌嗪衍生物是通过拆分方法使用市售的旋光酸制备的，相应的DABCO衍生物的收率为51-64％，最高可达99％ ％ee。这种温和的环化作用也可用于对映体纯的樟脑二胺衍生物，且产品收率为72–86％。
• Hg(II)-Selective Excimer Emission of a Bisnaphthyl Azadiene Derivative
  作者：Yasuhiro Shiraishi、Hajime Maehara、Katsutake Ishizumi、Takayuki Hirai

  DOI：10.1021/ol0713133

  日期：2007.8.1

  [GRAPHICS]A bisnaphthyl azadiene derivative (L) demonstrates Hg2+-selective intermolecular excimer emission. This emission is responsive to the number of coordinated Hg2+ atoms, where 2 : 2 and 2 : 3 L-Hg2+ complexes are the strongly emissive components, whereas the 2 : 1 complex is nonemissive.