1-(4-chlorophenacyl)-1,10-phenanthrolinium bromide | 468084-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 1-(4-chlorophenacyl)-1,10-phenanthrolinium bromide
• 英文别名: N-(p-chlorophenacyl)-1,10-phenanthrolinium bromide；1,10-Phenanthrolinium, 1-[2-(4-chlorophenyl)-2-oxoethyl]-, bromide；1-(4-chlorophenyl)-2-(1,10-phenanthrolin-1-ium-1-yl)ethanone;bromide
• CAS: 468084-08-4
• 化学式: Br*C₂₀H₁₄ClN₂O
• 分子量: 413.701
• InChiKey: TVTFLIDWQMIZTC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  33.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氰基甲酸乙酯 、 1-(4-chlorophenacyl)-1,10-phenanthrolinium bromide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以45%的产率得到1-(2-(4-chlorophenyl)-2-oxoethyl)-2-oxo-1,2-dihydro-1,10-phenanthroline-4-carbonitrile
  参考文献：
  名称：

  氰基甲酸乙酯与环铵盐的反应：稠合或取代的氮杂杂环的直接途径

  摘要：

  当在三乙胺介质中用氰基甲酸乙酯处理时，芳族环亚铵盐会经历不同的反应途径，包括选择性的γ-氰基取代（在菲咯啉鎓和喹啉鎓盐的情况下）和3 + 2偶极环加成反应（对于邻苯二甲酸和异喹啉鎓盐）。当使用phthalazinium盐，除了3个+ 2环加成产物（咪唑并[2,1-一个]酞嗪），我们得到8,8一，16,16一个-tetrahydropyrazino- [2,1-一个; 4,5-一个′]-二酞嗪通过3 + 3环加成二聚化作为副产物。合成的化合物的结构已通过光谱数据和三种新衍生物的X射线衍射证明。

  DOI：

  10.1016/j.tet.2016.05.061
• 作为产物：
  描述：

  1,10-菲罗啉 、 2'-溴-4-氯苯乙酮 以 丙酮 为溶剂， 反应 24.0h， 以79%的产率得到1-(4-chlorophenacyl)-1,10-phenanthrolinium bromide
  参考文献：
  名称：

  Helical chirality of 1-phenacyl-1,10-phenanthrolinium bromides

  摘要：

  Evidence for non-coplanarity of the pyridine and pyridinium rings in a series of 1-phenacyl-1,10- phenanthrolinium bromides was gleaned from H-1-NMR data recorded in DMSO-d(6) solution. The X-ray structure of 1-(4-chlorophenacyl)-1,10-phenanthrolinium bromide, as representative of this series, was determined in order to establish whether such a molecular distortion occurs in the solid state. The title compound crystallizes in the space group C2/c as a sesquihydrate of formula C20H14BrClN2O . 1.5H(2)O with a = 35.7348( 3) Angstrom, b = 5.3468( 1) Angstrom, c = 21.7312( 2) Angstrom, = 116.4076(4)degrees and Z = 8. In the crystal, the helical chirality is manifested as a pronounced twist in the phenanthrolinium moiety, with the pyridine and pyridinium rings inclined at 6.8(2)degrees. This distortion is attributed to intramolecular hydrogen bonding of type C H ... N involving the methylene group and the uncharged nitrogen atom of the phenanthrolinium moiety. In the crystal, the cations surround an intricate array of water molecules and bromide ions held together by O-H ... Br- hydrogen bonds and comprising infinite chains ... Br- ... H-O-H ... Br-..., cross-linked by water molecules.

  DOI：

  10.1023/b:jocc.0000044083.04054.9d

文献信息

• Synthesis of novel phenanthroline derivatives by 3+2 dipolar cycloadition reaction
  作者：Ramona Danac、Alexandra Rotaru、Gabi Drochioiu、Ioan Druta

  DOI：10.1002/jhet.5570400213

  日期：2003.3

  Eleven new 1,10-phenanthroline derivatives have been prepared by 3+2 dipolar cycloaddition reactions of 1,10-phenanthrolinium-ylides 7–12 in situ generated from corresponded salts, with dimethyl acetylene-dicarboxylate and ethyl propiolate.

  通过由相应的盐就地生成的1,10-菲咯啉鎓盐7-12 的3 + 2偶极环加成反应，乙炔-二羧酸二甲酯和丙酸乙酯，已经制备了11种新的1,10-菲咯啉衍生物。
• Reactions of ethyl cyanoformate with cycloimmonium salts: a direct pathway to fused or substituted azaheterocycles
  作者：Cristina M. Al Matarneh、Mircea O. Apostu、Ionel I. Mangalagiu、Ramona Danac

  DOI：10.1016/j.tet.2016.05.061

  日期：2016.7

  Aromatic cycloimmonium salts underwent different reaction pathways when treated with ethyl cyanoformate in triethyl amine medium, including selective γ-cyano substitutions (in case of phenanthrolinium and quinolinium salts) and 3+2 dipolar cycloadditions (for phthalazinium and isoquinolinium salts). When using phthalazinium salts, besides the 3+2 cycloaddition products (imidazo[2,1-a]phthalazines)

  当在三乙胺介质中用氰基甲酸乙酯处理时，芳族环亚铵盐会经历不同的反应途径，包括选择性的γ-氰基取代（在菲咯啉鎓和喹啉鎓盐的情况下）和3 + 2偶极环加成反应（对于邻苯二甲酸和异喹啉鎓盐）。当使用phthalazinium盐，除了3个+ 2环加成产物（咪唑并[2,1-一个]酞嗪），我们得到8,8一，16,16一个-tetrahydropyrazino- [2,1-一个; 4,5-一个′]-二酞嗪通过3 + 3环加成二聚化作为副产物。合成的化合物的结构已通过光谱数据和三种新衍生物的X射线衍射证明。
• Helical chirality of 1-phenacyl-1,10-phenanthrolinium bromides
  作者：Florea Dumitraşcu、Mino R. Caira、Constantin Drăghici、Miron Teodor Căproiu、Andrei Bădoiu

  DOI：10.1023/b:jocc.0000044083.04054.9d

  日期：2004.9

  Evidence for non-coplanarity of the pyridine and pyridinium rings in a series of 1-phenacyl-1,10- phenanthrolinium bromides was gleaned from H-1-NMR data recorded in DMSO-d(6) solution. The X-ray structure of 1-(4-chlorophenacyl)-1,10-phenanthrolinium bromide, as representative of this series, was determined in order to establish whether such a molecular distortion occurs in the solid state. The title compound crystallizes in the space group C2/c as a sesquihydrate of formula C20H14BrClN2O . 1.5H(2)O with a = 35.7348( 3) Angstrom, b = 5.3468( 1) Angstrom, c = 21.7312( 2) Angstrom, = 116.4076(4)degrees and Z = 8. In the crystal, the helical chirality is manifested as a pronounced twist in the phenanthrolinium moiety, with the pyridine and pyridinium rings inclined at 6.8(2)degrees. This distortion is attributed to intramolecular hydrogen bonding of type C H ... N involving the methylene group and the uncharged nitrogen atom of the phenanthrolinium moiety. In the crystal, the cations surround an intricate array of water molecules and bromide ions held together by O-H ... Br- hydrogen bonds and comprising infinite chains ... Br- ... H-O-H ... Br-..., cross-linked by water molecules.