6,13-Bis(4-ethynylphenyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone | 157500-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6,13-Bis(4-ethynylphenyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• 英文别名: 6,13-bis(4-ethynylphenyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 157500-66-8
• 化学式: C₃₀H₁₄N₂O₄
• 分子量: 466.452
• InChiKey: KOXZFIVNZXYVFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,13-Bis(4-ethynylphenyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone 、 tris(p-tert-butylphenyl)(4-(4-azidobutoxy)phenyl)methane 在 copper diacetate 、 silica gel 、 sodium ascorbate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以85%的产率得到
  参考文献：
  名称：

  Liquid-Assisted One-Pot Mechanosynthesis and Properties of Neutral Donor–Acceptor [2]Rotaxanes

  摘要：

  An efficient liquid-assisted one-pot two-step synthesis of neutral donor-acceptor,[2]rotaxanes has been successfully realized under high-speed vibration milling conditions, by taking advantage of the donor acceptor interaction between the electron-rich naphthalene unit of a macrocyclic polyether and the electron-deficient naphthalene diimide unit of a thread component for the threading process and click reaction as the stoppering process. The present method provides a powerful, fast, and environmentally benign alternative to traditional solvent-based approaches due to its notable advantages such as very small amount of solvent, no external heating, shorter reaction time, and higher yield. In addition, the charge-transfer interaction and electrochemically induced shuttling of the synthesized neutral donor-acceptor [2]rotaxanes have been demonstrated.

  DOI：

  10.1021/acs.joc.7b00912
• 作为产物：
  描述：

  4-乙炔基苯胺 、 1,4,5,8-萘四甲酸酐 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以59%的产率得到6,13-Bis(4-ethynylphenyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
  参考文献：
  名称：

  Koshkakaryan, Gayane; Klivansky, Liana M.; Cao, Dennis, Journal of the American Chemical Society, 2009, vol. 131, p. 2078 - 2079

  摘要：

  DOI：

文献信息

• Koshkakaryan, Gayane; Klivansky, Liana M.; Cao, Dennis, Journal of the American Chemical Society, 2009, vol. 131, p. 2078 - 2079
  作者：Koshkakaryan, Gayane、Klivansky, Liana M.、Cao, Dennis、Snauko, Marian、Teat, Simon J.、et al.

  DOI：——

  日期：——
• Liquid-Assisted One-Pot Mechanosynthesis and Properties of Neutral Donor–Acceptor [2]Rotaxanes
  作者：Hai-Gen Li、Guan-Wu Wang

  DOI：10.1021/acs.joc.7b00912

  日期：2017.6.16

  An efficient liquid-assisted one-pot two-step synthesis of neutral donor-acceptor,[2]rotaxanes has been successfully realized under high-speed vibration milling conditions, by taking advantage of the donor acceptor interaction between the electron-rich naphthalene unit of a macrocyclic polyether and the electron-deficient naphthalene diimide unit of a thread component for the threading process and click reaction as the stoppering process. The present method provides a powerful, fast, and environmentally benign alternative to traditional solvent-based approaches due to its notable advantages such as very small amount of solvent, no external heating, shorter reaction time, and higher yield. In addition, the charge-transfer interaction and electrochemically induced shuttling of the synthesized neutral donor-acceptor [2]rotaxanes have been demonstrated.