4-Chlor-N-fluorenylidenanilin | 5455-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-Chlor-N-fluorenylidenanilin
• 英文别名: 4-Chloro-n-(9h-fluoren-9-ylidene)aniline；N-(4-chlorophenyl)fluoren-9-imine
• CAS: 5455-00-5
• 化学式: C₁₉H₁₂ClN
• 分子量: 289.764
• InChiKey: GGECLVLMUAJEGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  4-Chlor-N-fluorenylidenanilin 生成 1-(4-chlorophenyl)spiro[aziridine-2,9'-fluorene]
  参考文献：
  名称：

  ABOU-GHARBIA MAGID; JOULLIE M. M., J. PHARM. SCI., 1977, 66, NO 11, 1653-1655

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-(4-chloro-phenyl)-5'-phenyl-spiro[fluorene-9,3'-pyrazole]-1'-carbonitrile 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 13.0h， 生成 4-Chlor-N-fluorenylidenanilin
  参考文献：
  名称：

  Eckell,A.; Huisgen,R., Chemische Berichte, 1977, vol. 110, p. 559 - 570

  摘要：

  DOI：

文献信息

• Synthesis of Benzo[<i>b</i>]fluoranthenes and Spiroacridines from Fluorene-Derived Alkenes and <i>N</i>-Arylimines via a Tandem Reaction with Benzynes
  作者：Weihua Wang、Hongwei Wan、Guangfen Du、Bin Dai、Lin He

  DOI：10.1021/acs.orglett.9b00659

  日期：2019.5.17

  Two tandem processes involving the cycloaddition of benzynes have been developed for the synthesis of polyaromatic hydrocarbons. Benzynes react with fluorene-derived alkenes through a tandem Diels–Alder reaction/dehydrogenation process to afford benzo[b]fluoranthenes in 35–87% yields. In addition, an unprecedented [2 + 2] cycloaddition/ring-opening sequence of benzynes and fluorene-derived N-arylimines

  已经开发了涉及联苯的环加成的两个串联方法来合成聚芳族烃。通过串联Diels-Alder反应/脱氢过程，苯并zy与芴衍生的烯烃反应，以35-87％的收率得到苯并[ b ]芴。此外，前所未有的[2 + 2]苯并炔和芴衍生的N-芳基嘧啶的环加成/开环顺序可轻松获得螺cr啶，收率为38-79％。
• Intramolecular addition of aryl radicals to carbon-nitrogen double bonds
  作者：Milena Gioanola、Rino Leardini、Daniele Nanni、Patrizia Pareschi、Giuseppe Zanardi

  DOI：10.1016/0040-4020(94)01068-b

  日期：1995.2

  5-exo cyclisation regiospecifically. A competitive 1,5-hydrogen shift leading to imidoyl radicals was noticed. An analogous behaviour is also exhibited by vinyl radicals when allowed to add to carbon-nitrogen double bonds.

  自由基6a，b的环化对5-exo过程具有高度区域选择性；6-内环闭环是次要路线，它们的比例取决于取代基。没有观察到五元自由基中间体7a，b的环膨胀。自由基27a，27b特异性地引起5-exo环化。注意到竞争性的1，5-氢转移导致亚氨基自由基。当被允许加成碳氮双键时，乙烯基基团也表现出类似的行为。
• Metal-free synthesis of highly substituted quinolines under mild conditions
  作者：Rakesh Natarajan、Peruparambil A. Unnikrishnan、Sandhya Radhamani、John P. Rappai、Sreedharan Prathapan

  DOI：10.1016/j.tetlet.2016.05.091

  日期：2016.7

  Starting from easily accessible nitrones and acetylenes, a simple, metal free synthesis of substituted quinolines under mild conditions with high atom efficiency has been developed. Our method is flexible enough to introduce substituents regiospecifically at the 2,3,4,6,8-positions of the quinoline product.

  从容易获得的硝酮和乙炔开始，已经开发了在温和条件下以高原子效率简单，无金属地合成取代喹啉的方法。我们的方法足够灵活，可以在喹啉产物的2,3,4,6,8-位上区域特异性地引入取代基。
• Synthesis of mono-, bis-spiro- and dispiro-β-lactams and evaluation of their antimalarial activities
  作者：Aliasghar Jarrahpour、Edris Ebrahimi、Erik De Clercq、Véronique Sinou、Christine Latour、Lamia Djouhri Bouktab、Jean Michel Brunel

  DOI：10.1016/j.tet.2011.09.041

  日期：2011.11

  Some new mono-, bis-spiro- and dispiro-β-lactams have been synthesized from imines derived from 9H-fluoren-9-one and a ketene derived from 9H-xanthene-9-carboxylic acid or phenoxyacetic acid by a [2+2] cycloaddition reaction in good to excellent yields varying from 45 to 83%. The biological activity of these monocyclic β-lactams was successfully investigated against Plasmodium falciparum K14 resistant

  某些新的单，双-螺和双-螺-β-内酰胺是由[9 H-芴-9-一]衍生的亚胺和由9 H -carboxylic吨9-羧酸或苯氧乙酸衍生的乙烯酮合成的[ [2 + 2]环加成反应的良好至优异收率从45％到83％不等。已成功研究了这些单环β-内酰胺类抗恶性疟原虫K14抗性菌株的生物学活性，该菌株的EC 50值高达5μM。
• Hydride, Hydrogen, Proton, and Electron Affinities of Imines and Their Reaction Intermediates in Acetonitrile and Construction of Thermodynamic Characteristic Graphs (TCGs) of Imines as a “Molecule ID Card”
  作者：Xiao-Qing Zhu、Qiao-Yun Liu、Qiang Chen、Lian-Rui Mei

  DOI：10.1021/jo902332n

  日期：2010.2.5

  A series of 61 imines with various typical structures were synthesized, and the thermodynamic affinities (defined as enthalpy changes or redox potentials in this work) of the imines to abstract hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the imines to abstract hydrogen atoms and protons, and the thermodynamic affinities of the hydrogen adducts of the imines to abstract electrons in acetonitrile were determined by using titration calorimetry and electrochemical methods. The pure heterolytic and homolytic dissociation energies of the C = N pi-bond in the imines were estimated. The polarity of the C = N double bond in the imines was examined using a linear free-energy relationship. The idea of a thermodynamic characteristic graph (TCG) of imines as an efficient "Molecule ID Card" was introduced. The TCG can be used to quantitatively diagnose and predict the characteristic chemical properties of imines and their various reaction intermediates as well as the reduction mechanism of the imines. The information disclosed in this work could not only supply a gap of thermodynamics for the chemistry of imines but also strongly promote the fast development of the applications of imines.