2,7-dinitro-9,9-di(prop-2-ynyl)fluorene | 1260521-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-dinitro-9,9-di(prop-2-ynyl)fluorene
• 英文别名: 2,7-Dinitro-9,9-bis(prop-2-ynyl)fluorene；2,7-dinitro-9,9-bis(prop-2-ynyl)fluorene
• CAS: 1260521-61-6
• 化学式: C₁₉H₁₂N₂O₄
• 分子量: 332.315
• InChiKey: LPBLXFDILVBNMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-dinitro-9,9-di(prop-2-ynyl)fluorene 在 titanium(IV) isopropylate 、 Wilkinson's catalyst 、 四丁基溴化铵 、 rongalite 、 三溴化磷 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 41.0h， 生成
  参考文献：
  名称：

  Diversity-oriented approach to linearly fused spirocycles via strategic utilization of a [2+2+2] cycloaddition and the Diels–Alder reaction

  摘要：

  We have demonstrated a simple and an efficient protocol for assembling a library of linearly fused spirocycles in a diversity-oriented manner by utilizing two sequential atom-economic reactions such as a [2+2+2] cycloaddition and the Diels-Alder (DA) reaction. Herein, we have used rongalite for the formation of sultine derivatives, which are useful latent diene equivalents suitable for the DA sequence to generate a library of polycycles under mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.009
• 作为产物：
  描述：

  2,7-二硝基芴 、 3-溴丙炔 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 为溶剂， 反应 5.5h， 以69%的产率得到2,7-dinitro-9,9-di(prop-2-ynyl)fluorene
  参考文献：
  名称：

  Spiro-Annelated Zn-Phthalocyanine: A Novel Building Block for Molecular Architecture?

  摘要：

  通过 [2+2+2] 乙炔环三聚反应的全新合成获得了一种芳香体系，从而得到了一种氟烯基螺环连接的邻苯二甲酸酐衍生物。其异常的刚性源自于正交连接的氟烯基部分，这一点通过单晶X射线分析得到了证实。该酐成功地作为前体用于合成一种新型的正交螺环连接的锌酞菁，具有作为分子架构核心的潜力。

  DOI：

  10.1055/s-0030-1258209

文献信息

• Spiro-Annelated Zn-Phthalocyanine: A Novel Building Block for Molecular Architecture?
  作者：Theo Schotten、Herwig Berthold、Joachim Thiem、Andrea Zaliani

  DOI：10.1055/s-0030-1258209

  日期：2010.10

  The de novo synthesis of an aromatic system via [2+2+2] alkyne cyclotrimerization provided access to a fluorenyl spiro-annelated­ phthalic anhydride derivative. Its exceptional rigidity - originating from the orthogonally attached fluorenyl moiety - was confirmed by single-crystal X-ray analysis. The anhydride was used successfully as a precursor for the synthesis of a novel class of orthogonal spiro-annelated Zn-phthalocyanine, which has the potential to be used as a core for molecular architecture.

  通过 [2+2+2] 乙炔环三聚反应的全新合成获得了一种芳香体系，从而得到了一种氟烯基螺环连接的邻苯二甲酸酐衍生物。其异常的刚性源自于正交连接的氟烯基部分，这一点通过单晶X射线分析得到了证实。该酐成功地作为前体用于合成一种新型的正交螺环连接的锌酞菁，具有作为分子架构核心的潜力。
• Molybdenum hexacarbonyl: air stable catalyst for microwave assisted intermolecular [2+2+2] co-trimerization involving propargyl halides
  作者：Sambasivarao Kotha、Gaddamedi Sreevani

  DOI：10.1016/j.tetlet.2015.09.029

  日期：2015.10

  Intermolecular [2+2+2] cycloaddition of propargyl halides with 1,6-diynes was achieved with air stable, catalytic amount of Mo(CO)(6) and the benzyl halide derivatives were isolated in good yields. The reaction conditions were optimized and better yields were observed under microwave irradiation conditions using acetonitrile as a solvent. (C) 2015 Elsevier Ltd. All rights reserved.
• Diversity-oriented approach to linearly fused spirocycles via strategic utilization of a [2+2+2] cycloaddition and the Diels–Alder reaction
  作者：Sambasivarao Kotha、Rashid Ali

  DOI：10.1016/j.tet.2015.01.009

  日期：2015.3

  We have demonstrated a simple and an efficient protocol for assembling a library of linearly fused spirocycles in a diversity-oriented manner by utilizing two sequential atom-economic reactions such as a [2+2+2] cycloaddition and the Diels-Alder (DA) reaction. Herein, we have used rongalite for the formation of sultine derivatives, which are useful latent diene equivalents suitable for the DA sequence to generate a library of polycycles under mild reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.