N-benzyl-4-nitrobenzimidoyl chloride | 3712-57-0

• 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: N-benzyl-4-nitrobenzimidoyl chloride
• 英文别名: N-benzyl-4-nitro-benzimidoyl chloride；4-Nitro-N-benzyl-benzimidsaeure-chlorid；Benzenecarboximidoyl chloride, 4-nitro-N-(phenylmethyl)-；N-benzyl-4-nitrobenzenecarboximidoyl chloride
• CAS: 3712-57-0
• 化学式: C₁₄H₁₁ClN₂O₂
• 分子量: 274.707
• InChiKey: UFIPNFCQAYSUOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-nitrobenzimidoyl chloride 在 碘苯二乙酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.17h， 生成 1-benzyl-2-(4-nitrophenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Solvent/Oxidant-Switchable Synthesis of Multisubstituted Quinazolines and Benzimidazoles via Metal-Free Selective Oxidative Annulation of Arylamidines

  摘要：

  A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp(3))-C(sp(2)) and C(sp(2))-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp(3)C-H/sp(2)C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.

  DOI：

  10.1021/ol500864r
• 作为产物：
  描述：

  苄胺 在 氯化亚砜 、 三乙胺 、 calcium chloride 作用下， 反应 4.0h， 生成 N-benzyl-4-nitrobenzimidoyl chloride
  参考文献：
  名称：

  New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase

  摘要：

  O-Perbenzoylated 5-(beta-D-glucopyranosyl)tetrazole was reacted with N-benzyl carboximidoyl chlorides to give the corresponding 4-benzyl-3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles. Removal of the O-benzoyl and N-benzyl protecting groups by base catalysed transesterification and catalytic hydrogenation, respectively, furnished a series of 3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles with aliphatic, mono- and bicyclic aromatic, and heterocyclic substituents in the 5-position. Enzyme kinetic studies revealed these compounds to inhibit rabbit muscle glycogen phosphorylase b: best inhibitors were the 5-(4-aminophenyl)- (K-i 0.67 mu M) and the 5-(2-naphthyl)-substituted (K-i 0.41 mu M) derivatives. This study uncovered the C-glucopyranosyl-1,2,4-triazoles as a novel skeleton for nanomolar inhibition of glycogen phosphorylase. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.041
• 作为试剂：
  描述：

  足球烯 、 三乙胺 在 N-benzyl-4-nitrobenzimidoyl chloride 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以2%的产率得到1,2-[3,4-dihydro-2-phenyl-5-(4-nitrophenyl)-2H-pyrrolo]-[60]-fullerene
  参考文献：
  名称：

  [60]富勒烯与4-硝基-N-苄基苯并亚胺酰氯和三乙胺的反应：一种合成[60]富勒烯-稠合吡咯啉的新方法

  摘要：

  摘要 由[60]富勒烯与亚氨酰氯和三乙胺反应得到两种异构的[60]富勒烯稠合吡咯啉和一种[60]富勒吡咯烷衍生物。

  DOI：

  10.1080/00397919708006072

文献信息

• Sigmatropic isomerizations in 2-aza-allylic systems. Part X. Prototropic and chlorotropic rearrangements in fluoroalkyl- substituted 1,3-dichloro-imines
  作者：P.P. Onys'ko、T.V. Kim、E.I. Kiseleva、A.D. Sinitsa

  DOI：10.1016/0022-1139(94)03133-9

  日期：1994.12

  The photochemical chlorination of N-benzylimidoyl chlorides RC(CI)=NCH2Ph (R=CF3, CFCI2, C3F7, tBu, Ar) results in RC(CI)=NCH(CI)Ph or its mixture with isomeric RCCI2N=CHPh depending on the nature of the substituent R. 1,3-Prototropic and 1,3-chlorotropic rearrangements in the chlorination products have been observed and investigated.

  N-苄基亚氨基酰氯RC（CI）= NCH 2 Ph（R = CF 3，CFCI 2，C 3 F 7，t Bu，Ar）的光化学氯化导致RC（CI）= NCH（CI）Ph或其混合物取决于取代基R的性质，其具有RCCI 2 N ＝ CHPh的异构体。已经观察到并研究了氯化产物中的1，3-丙酸和1，3-氯酸重排。
• Bunge,K. et al., Chemische Berichte, 1972, vol. 105, p. 1307 - 1323
  作者：Bunge,K. et al.

  DOI：——

  日期：——
• Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I., Journal of general chemistry of the USSR, 1987, vol. 57, # 6, p. 1104 - 1110
  作者：Onys'ko, P. P.、Kim, T. V.、Kiseleva, E. I.、Sinitsa, A. D.

  DOI：——

  日期：——
• Onys'ko, P. P.; Kim, T. V.; Kiseleva, E. I., Journal of general chemistry of the USSR, 1990, vol. 60, # 3, p. 455 - 458
  作者：Onys'ko, P. P.、Kim, T. V.、Kiseleva, E. I.、Prokopenko, V. P.、Sinitsa, A. D.

  DOI：——

  日期：——
• New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase
  作者：Sándor Kun、Éva Bokor、Gergely Varga、Béla Szőcs、András Páhi、Katalin Czifrák、Marietta Tóth、László Juhász、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.ejmech.2014.02.041

  日期：2014.4

  O-Perbenzoylated 5-(beta-D-glucopyranosyl)tetrazole was reacted with N-benzyl carboximidoyl chlorides to give the corresponding 4-benzyl-3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles. Removal of the O-benzoyl and N-benzyl protecting groups by base catalysed transesterification and catalytic hydrogenation, respectively, furnished a series of 3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles with aliphatic, mono- and bicyclic aromatic, and heterocyclic substituents in the 5-position. Enzyme kinetic studies revealed these compounds to inhibit rabbit muscle glycogen phosphorylase b: best inhibitors were the 5-(4-aminophenyl)- (K-i 0.67 mu M) and the 5-(2-naphthyl)-substituted (K-i 0.41 mu M) derivatives. This study uncovered the C-glucopyranosyl-1,2,4-triazoles as a novel skeleton for nanomolar inhibition of glycogen phosphorylase. (C) 2014 Elsevier Masson SAS. All rights reserved.