2-formyl-3-[N'-(ω-chloroacetyl)-N'-(4-nitrophenyl)amino]indole | 658041-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-formyl-3-[N'-(ω-chloroacetyl)-N'-(4-nitrophenyl)amino]indole
• 英文别名: 3-[N-(chloroacetyl)-N-(4-nitrophenyl)amino]-2-formylindole；3-[N-chloroacetyl-N-(4-nitrophenyl)amino]-2-formylindole；2-chloro-N-(2-formyl-1H-indol-3-yl)-N-(4-nitrophenyl)acetamide
• CAS: 658041-39-5
• 化学式: C₁₇H₁₂ClN₃O₄
• 分子量: 357.753
• InChiKey: QNXUBZBAFFMAAE-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C(Solv: isopropanol (67-63-0))
• 沸点：
  712.1±60.0 °C(Predicted)
• 密度：
  1.522±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-formyl-3-[N'-(ω-chloroacetyl)-N'-(4-nitrophenyl)amino]indole 在 甲烷 、 对甲苯磺酸 作用下， 反应 10.17h， 生成 3-[N-chloroacetyl-N-(4-nitrophenyl)amino]-2-formylindole diethyl acetal
  参考文献：
  名称：

  摘要：

  A number of 1-aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole 4-oxides were synthesized based on 3-[N-aryl-N-(chloroacetyl)amino]-2-formylindoles. The nature of the substituent in the 1-aryl fragment has a pronounced influence on the course of reactions throughout the whole sequence of transformations during the synthesis of diazepinoindoles. The reduction of 4-oxides by formamidinosulfinic acid, hydrogen in the presence of Pd/C, and sodium bisulfite was studied. The structures of the reaction products were confirmed using IR and H-1 NMR spectroscopy and mass spectrometry.

  DOI：

  10.1023/a:1024887429776
• 作为产物：
  描述：

  3-[N-(4-nitrophenyl)amino]indole 在 水 、 sodium carbonate 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 6.5h， 生成 2-formyl-3-[N'-(ω-chloroacetyl)-N'-(4-nitrophenyl)amino]indole
  参考文献：
  名称：

  摘要：

  A number of 1-aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole 4-oxides were synthesized based on 3-[N-aryl-N-(chloroacetyl)amino]-2-formylindoles. The nature of the substituent in the 1-aryl fragment has a pronounced influence on the course of reactions throughout the whole sequence of transformations during the synthesis of diazepinoindoles. The reduction of 4-oxides by formamidinosulfinic acid, hydrogen in the presence of Pd/C, and sodium bisulfite was studied. The structures of the reaction products were confirmed using IR and H-1 NMR spectroscopy and mass spectrometry.

  DOI：

  10.1023/a:1024887429776

文献信息

• Synthesis of 4-aminopyrido[3,2-b]indole derivatives
  作者：S. Yu. Ryabova、L. M. Alekseeva、E. A. Lisitsa、V. G. Granik

  DOI：10.1007/s11172-006-0407-8

  日期：2006.7

  3-Arylamino-2-formylindoles were converted into oximes and then acetylated to give the corresponding O-acetyl derivatives. Chloroacetylation of the latter was accompanied by elimination of acetic acid, yielding 3-(N-aryl-N-chloroacetyl)amino-2-cyanoindoles. When heated in pyridine, these nitriles underwent cyclization into novel δ-carboline derivatives: 4-amino-1-aryl-2-oxo-1,2-dihydropyrido[3,2-b]indol-3-yl)pyridinium chlorides. The structures of the compounds obtained were proved by IR and 1H NMR spectroscopy and mass spectrometry.

  将 3-芳基氨基-2-甲酰基吲哚转化为肟，然后进行乙酰化，得到相应的 O-乙酰基衍生物。后者的氯乙酰化伴随着乙酸的消除，生成 3-（N-芳基-N-氯乙酰基）氨基-2-氰基吲哚。在吡啶中加热后，这些腈类发生环化反应，生成新型的 δ-咔啉衍生物：4-氨基-1-芳基-2-氧代-1,2-二氢吡啶并[3,2-b]吲哚-3-基）吡啶鎓氯化物。通过红外光谱、1H NMR 光谱和质谱分析证明了所获化合物的结构。
• Reactions of 3-[N-chloroacetylamino-N-(4-nitrophenyl)]-2-formylindole with alkylamines
  作者：S. Yu. Ryabova、A. S. Shashkov、L. M. Alekseeva、E. A. Lisitsa、V. G. Granik

  DOI：10.1007/s11172-007-0249-z

  日期：2007.8

  The reactions of 3-[N-chloracetylamino-N-(4-nitrophenyl)]-2-formylindole (1a) with 2-(N, N-dialkylamino)ethylamines afford complex condensation products 7b,c consisting of two similar but not identical diazepinoindole fragments. For the reaction of compound 1a with 3-(N,N-diethylamino)propylamine, the process occurs in a different manner, and the predominant product is 4-ethylaminopropyl-1-(4-nitrophenyl)-2-oxo-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole hydrocloride (14). Two routes of these unexpected transformations were proposed. The structures of the synthesized products were proved by the 1sH and 13C NMR, HMBC, and HSQC (direct proton-carbon correlation) spectra.

  3-[N-氯乙酰氨基-N-(4-硝基苯基)]-2-甲酰基吲哚（1a）与2-(N,N-二烷基氨基)乙胺的反应生成复杂的缩合产物7b,c，由两个相似但不相同的二氮杂吲哚片段组成。对于化合物1a与3-(N,N-二乙基氨基)丙胺的反应，反应过程以不同的方式进行，主要产物是4-乙基氨基丙基-1-(4-硝基苯基)-2-氧代-1,2,3,4,5,6-六氢[1,4]二氮杂吲哚[6,5-b]吲哚盐酸盐（14）。提出了两种意想不到的转化途径。合成产物的结构通过1sH和13C NMR、HMBC和HSQC（直接质子-碳相关）光谱进行了验证。
• Synthesis of derivatives of a new heterocyclic system, indolo[2,3-f][1,7]naphthyridine
  作者：N. A. Rastorgueva、S. Yu. Ryabova、E. A. Lisitsa、L. M. Alekseeva、V. G. Granik

  DOI：10.1023/b:rucb.0000011871.28637.78

  日期：2003.10

  3-(N'-Aryl-N'-cliloroacetyl)amino-2-formyliildoles were converted into 3-amino-1-aryl2-oxo-1,2-dihvdropyrido[3,2-b]indoles, which were used to synthesize derivatives of a new heterocyclic system, namely, indolo [2.3-f][1,7] naphthyridine. The structures of the resulting Compounds were proved by IR and H-1 NMR spectroscopy and mass spectrometry.
• ——
  作者：S. Yu. Ryabova、N. A. Rastorgueva、E. A. Lisitsa、L. M. Alekseeva、V. G. Granik

  DOI：10.1023/a:1024887429776

  日期：——

  A number of 1-aryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole 4-oxides were synthesized based on 3-[N-aryl-N-(chloroacetyl)amino]-2-formylindoles. The nature of the substituent in the 1-aryl fragment has a pronounced influence on the course of reactions throughout the whole sequence of transformations during the synthesis of diazepinoindoles. The reduction of 4-oxides by formamidinosulfinic acid, hydrogen in the presence of Pd/C, and sodium bisulfite was studied. The structures of the reaction products were confirmed using IR and H-1 NMR spectroscopy and mass spectrometry.