3-N,N-dimethylamino-1-(4-nitrophenyl)-propene-1-thione | 78089-92-6

• 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-N,N-dimethylamino-1-(4-nitrophenyl)-propene-1-thione
• 英文别名: 3-N,N-Dimethylamino-1-(4-nitrophenyl)-prop-2-en-1-thion；Djjakihltfnnfw-bqyqjahwsa-；(E)-3-(dimethylamino)-1-(4-nitrophenyl)prop-2-ene-1-thione
• CAS: 78089-92-6
• 化学式: C₁₁H₁₂N₂O₂S
• 分子量: 236.294
• InChiKey: DJJAKIHLTFNNFW-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-N,N-dimethylamino-1-(4-nitrophenyl)-propene-1-thione 在 溶剂黄146 作用下， 以 苯 为溶剂， 生成 3-Nitro-6-(4-nitrophenyl)-2-phenyl-2H-thiopyran
  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：

  (E)-3-二甲氨基-1-(4-硝基苯基)-2-丙烯-1-酮 在 劳森试剂 、 sodium hydroxide 作用下， 反应 1.0h， 以80%的产率得到3-N,N-dimethylamino-1-(4-nitrophenyl)-propene-1-thione
  参考文献：
  名称：

  烯胺化学-XXVI：3-氨基-1-（4-硝基苯基）-丙-2-烯-1-硫酮与亲电烯烃和乙炔的[4 + 2]环加成反应

  摘要：

  由相应的烯胺酮通过用Lawesson's Reagent缩合制备的烯氨基硫酮1与2-氯丙烯腈和乙炔二羧酸二甲酯反应，分别得到二氢2H-硫吡喃2和4H-硫吡喃3。1a与丙酸乙酯在室温下反应，得到4H-噻喃基4a，静置后重排为2H-硫代吡喃5a（1，3酰胺位移）。1b与丙酸乙酯反应生成4b和5b。报道了一些13 C NMR数据。

  DOI：

  10.1016/0040-4020(82)80151-8

文献信息

• Modular Synthesis of Fluorinated 2<i>H</i>-Thiophenes via [4+1] Cyclization of Enaminothiones
  作者：Xinyu Zhang、Jinli Zhang、Jie Chen、Banghua Zhou、Jian Zhang、Shunhong Chen、Jian Wu、Yaojia Jiang

  DOI：10.1039/d3ob00222e

  日期：——

  An efficient and straightforward synthetic method for constructing trifluoromethyl 2H-thiophenes through [4 + 1] cycloaddition of enaminothiones with trifluoromethyl N-tosylhydrazones has been disclosed. The cycloaddition platforms were found to be compatible with a broad substrate scope and to show high regio- and stereo-selectivities under very mild reaction conditions such as room temperature, neutral

  已公开了一种通过烯胺硫酮与三氟甲基N-甲苯磺酰腙的 [4 + 1] 环加成反应构建三氟甲基 2 H-噻吩的有效且直接的合成方法。发现环加成平台与广泛的底物范围兼容，并在非常温和的反应条件下（如室温、中性介质和催化剂负载量低）显示出高区域选择性和立体选择性。
• Borohydride and cyanoborohydride reduction of thioimonium salts. A convenient route for transformation of amides to amines
  作者：Richard J. Sundberg、Claudia Powers Walters、Jonathan D. Bloom

  DOI：10.1021/jo00331a032

  日期：1981.8
• Greif, D; Pulst, M.; Weissenfels, M., Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 6, p. 863 - 873
  作者：Greif, D、Pulst, M.、Weissenfels, M.、Scheinmann, Feodor

  DOI：——

  日期：——
• SUNDBERG, R. J.;WALTERS, C. P.;BLOOM, J. D., J. ORG. CHEM., 1981, 46, N 18, 3730-3732
  作者：SUNDBERG, R. J.、WALTERS, C. P.、BLOOM, J. D.

  DOI：——

  日期：——
• RASMUSSEN, J. B.;SHABANA, R.;LAWESSON, S. -O., TETRAHEDRON, 1982, 38, N 11, 1705-1709
  作者：RASMUSSEN, J. B.、SHABANA, R.、LAWESSON, S. -O.

  DOI：——

  日期：——

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