3-chloro-3-(4-nitrophenyl)-prop-2-en-1-ylidenedimethyliminium perchlorate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-3-(4-nitrophenyl)-prop-2-en-1-ylidenedimethyliminium perchlorate
• 英文别名: 3-Chlor-3-(4-nitrophenyl)-prop-2-en-1-yliden-dimethyliminium-perchlorat；3-Chlor-3-p-nitrophenyl-prop-2-en-1-yliden-dimethyliminium-perchlorat；Methanaminium, N-(3-chloro-3-(4-nitrophenyl)-2-propenylidene)-N-methyl-, perchlorate；[(Z)-3-chloro-3-(4-nitrophenyl)prop-2-enylidene]-dimethylazanium;perchlorate
• 化学式: C₁₁H₁₂ClN₂O₂*ClO₄
• 分子量: 339.132
• InChiKey: CSBFFIDCILZUHT-AJULUCINSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.24
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-chloro-3-(4-nitrophenyl)-prop-2-en-1-ylidenedimethyliminium perchlorate 在 sodium sulfide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到3-N,N-dimethylamino-1-(4-nitrophenyl)-propene-1-thione
  参考文献：
  名称：

  Synthese neuer, 3-substituierter 2H-Thiopyran-Derivate via [4+2]-Cycloaddition mittels acceptorsubstituierter Enaminothione

  摘要：

  3- and 4-Nitro acetophenones as well as 3- and 4-trifluoromethyl acetophenones react with POCl3/DMF (Vilsmeier reagent) to give dimethyliminium perchlorates 1a-d after addition of perchloric acid to the reaction mixture. Substitution of the chloro atom in 1 by using sodium sulfide nonahydrate occurs under mild conditions (in case of nitro compounds at -5-degrees-C) leading to enaminothiones 2a-d. Reactions with acroleine and methylvinylketone in refluxing benzene give exclusively 2H-thiopyran derivatives 4a-h, which were isolated in good yields after spontaneous fast elimination of dimethylamine. In contrast, the introduction of 1-nitro-2-phenylethene as the dienophile allows stepwise reaction to give stable adducts 3k and 3l, respectively, and also 3m under mild conditions (reaction at room temperature). H-1 n.m.r. spectroscopic data as well as the elimination of dimethylamine to 4k-m permit the elucidation of the structure of adducts 3k-m.

  DOI：

  10.1002/prac.19943360510
• 作为产物：
  描述：

  对硝基苯乙酮 以65%的产率得到
  参考文献：
  名称：

  LIEBSCHER J.; HARTMANN H., J. PRAKT. CHEM., 1976, 318, NO 5, 705-730

  摘要：

  DOI：

文献信息

• Pyridinderivate aus 3-Chlor-2-propeniminiumsalzen und Enaminen
  作者：Bernd Brinker、Dieter Heber

  DOI：10.1002/ardp.19873200608

  日期：——

  Reaktionen der 3‐Chlor‐2‐propeniminiumsalze 1 führen in Abhängigkeit von der Struktur der Enamine 2, 3 und 21 entweder zu den 1,4‐Dihydropyridinen 8 und 9 oder zu einem Gemisch der isomeren 5‐ bzw. 7‐arylsubstituierten Pyrido[2,3‐d]pyrimidine 22 und 23, deren Struktur anhand der 1H‐NMR‐Spektren diskutiert wird.

  根据烯胺 2、3 和 21 的结构，3-氯-2-丙烯亚胺盐 1 的反应生成 1,4-二氢吡啶 8 和 9 或生成 5- 或 7-芳基异构体的混合物-取代的吡啶并 [2 , 3 - d] 嘧啶 22 和 23，其结构根据 1H NMR 光谱进行讨论。
• Fischer, G. W.; Herrmann, M., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 6, p. 963 - 973
  作者：Fischer, G. W.、Herrmann, M.

  DOI：——

  日期：——
• On the synthesis and structure of 8-nitro-imidazo[1,2-a]pyridines
  作者：Harry Sch�fer、Margit Gruner、Gisbert Gro�mann、Karl Gewald

  DOI：10.1007/bf00823426

  日期：1991.11

  The title compounds were synthesized by reaction of nitroketene animals with beta-chlorovinylcarbonyl compounds. The chloromethylene malononitriles 1 react with nitromethylenimidazolin (2 a) and -benzimidazoles 2 b to yield the 8-nitro-2,3-dihydroimidazo[1,2-a]pyridines 3 and the 4-nitropyrido[1,2-a]-benzimidazoles 6, both containing an amino group. Analogously, from the special 3-chloro-2-propeniminium salt 7 and 2 a the imidazopyridine derivative 9 was formed. The 3-aryl-3-chloro-2-propeniminium salts 10 were converted into the nitro-dihydroimidazo[1,2-a]pyridines 11 and the pyrido[1,2-a]benzimidazole 12 containing the aryl group by reaction with 2 a and 2 b, respectively. The structures were investigated by 2-dimensional H-1/C-13-NMR-spectroscopy.
• An efficient, regiocontrolled synthesis of 5-aryl-2-carbethoxypyrroles from 3-aryl-3-chloropropeniminium salts
  作者：John T. Gupton、Dale A. Krolikowski、Richard H. Yu、Vu Phong、James A. Sikorski、Maria L. Dahl、Claude R. Jones

  DOI：10.1021/jo00046a033

  日期：1992.9

  A variety of 3-aryl-3-chloropropeniminium salts react with alpha-amino acid esters under basic conditions to produce 2-carbethoxy-5-arylpyrroles in a regioselective manner. The overall process represents a short, efficient, and convergent synthesis of 2,5-disubstituted pyrroles, and azomethine ylides or azapentadienyl anions may be involved as intermediates.
• SCHNEIDER P.; FISCHER G. W., J. PRAKT. CHEM., 1980, 322, NO 2, 229-236
  作者：SCHNEIDER P.、 FISCHER G. W.

  DOI：——

  日期：——