N-benzyl-4-nitrobenzenecarboximidoyl 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-nitrobenzenecarboximidoyl chloride
• 英文别名: N-benzyl-4-nitrobenzimidoyl chloride
• CAS: 3712-57-0
• 化学式: C₁₄H₁₁ClN₂O₂
• 分子量: 274.707
• InChiKey: UFIPNFCQAYSUOG-PEZBUJJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.5
• 氢给体数：
  0.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-nitrobenzenecarboximidoyl chloride 以 丙酮 为溶剂， 反应 0.5h， 生成 N-benzyl-N'-[(morpholin-4-yl)(selenocarbonyl)]-4-nitrobenzimidamide
  参考文献：
  名称：

  Synthesis of Bis(2,4-diarylimidazol-5-yl) Diselenides from N-Benzylbenzimidoyl Isoselenocyanates

  摘要：

  The reaction of N-benzylbenzamides 6 with SOCl2 under reflux gave the corresponding N-benzylbenzimidoyl chlorides 7. Further treatment with KSeCN in dry acetone yielded imidoyl isosclenocyanates 3 (Scheme 2). These compounds, obtained in satisfying yields, proved to be stable enough to be purified and analyzed. Reaction of 3 with morpholine in dry acetone led to the corresponding selonourea derivatives 8. On treatment with Et3N, the 4-nitrobenzyl derivatives of type 3 were transformed into bis(2,4-diarylimidazol-5-yl) diselenides 9 (Scheme 3). This transformation takes place only when the benzyl residue bears an NO2 group and the phenyl group is not substituted with a strong electron-donating group. A reaction mechanism for the formation of 9 is proposed in Scheme 4. The key structures have been established by X-ray crystallography.

  DOI：

  10.1002/1522-2675(200204)85:4<1102::aid-hlca1102>3.0.co;2-t
• 作为产物：
  描述：

  N-苄基-4-硝基苯甲酰胺 在 氯化亚砜 作用下， 生成 N-benzyl-4-nitrobenzenecarboximidoyl chloride
  参考文献：
  名称：

  Synthesis of Bis(2,4-diarylimidazol-5-yl) Diselenides from N-Benzylbenzimidoyl Isoselenocyanates

  摘要：

  The reaction of N-benzylbenzamides 6 with SOCl2 under reflux gave the corresponding N-benzylbenzimidoyl chlorides 7. Further treatment with KSeCN in dry acetone yielded imidoyl isosclenocyanates 3 (Scheme 2). These compounds, obtained in satisfying yields, proved to be stable enough to be purified and analyzed. Reaction of 3 with morpholine in dry acetone led to the corresponding selonourea derivatives 8. On treatment with Et3N, the 4-nitrobenzyl derivatives of type 3 were transformed into bis(2,4-diarylimidazol-5-yl) diselenides 9 (Scheme 3). This transformation takes place only when the benzyl residue bears an NO2 group and the phenyl group is not substituted with a strong electron-donating group. A reaction mechanism for the formation of 9 is proposed in Scheme 4. The key structures have been established by X-ray crystallography.

  DOI：

  10.1002/1522-2675(200204)85:4<1102::aid-hlca1102>3.0.co;2-t

文献信息

• Synthesis of 2H-pyrroles via the 1,3-dipolar cycloaddition reaction of nitrile ylides with acrylamides
  作者：Choong Leol Yoo、Marilyn M. Olmstead、Dean J. Tantillo、Mark J. Kurth

  DOI：10.1016/j.tetlet.2005.11.066

  日期：2006.1

  3,4-Dihydro-2H-pyrrole derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of nitrile ylides with acrylamides. Acrylamide substitution patterns and benzimidoyl chloride equilibration were investigated.

  通过腈与丙烯酰胺的1，3-偶极环加成反应合成了3，4-二氢-2 H-吡咯衍生物。研究了丙烯酰胺的取代方式和苯甲酰氯的平衡。
• Cycloaddition reaction of 1-(4-nitrophenyl)-3-phenylnitrile ylide to buckminsterfullerene[60]
  作者：A.A. Ovcharenko、V.A. Chertkov、A.V. Karchava、M.A. Yurovskaya

  DOI：10.1016/s0040-4039(97)01625-0

  日期：1997.9

  situ from N-benzyl-4-nitrobenzimidoyl chloride to C60 yields to 1,2-[3,4-dihydro-2-phenyl-5-(4-nitrophenyl)-2H- pyrrolo]-[60]fullerene and diastereomeric mixture of two 5,6-open isomers. Moreover, double carbon-nitrogen bond of 5,6-open of adduct is located in α position to unsubstituted phenyl ring.

  从N-苄基-4-硝基苯并亚甲基氯酰原位生成的1-（4-硝基苯基）-3-苯基腈内酯与C 60环加成，生成1,2- [3,4-二氢-2-苯基-5-（4） -硝基苯基）-2 H-吡咯]-[60]富勒烯与两种5,6-开放异构体的非对映异构体混合物。另外，加合物的5，6-开口的碳-氮双键位于未取代的苯环的α位。
• Revisit to the reaction of [60]fullerene with nitrile ylides generated from imidoyl chlorides and triethylamine
  作者：Guan-Wu Wang、Hai-Tao Yang

  DOI：10.1016/j.tetlet.2007.04.085

  日期：2007.6

  The reaction of [60]fullerene (C60) with nitrile ylides generated from N-benzyl-4-nitrobenzimidoyl chloride/N-(4-chlorobenzyl)-4-nitrobenzimidoyl chloride and triethylamine gave only isomeric monoadducts of C60 with [6,6]-closed structure. No [5,6]-open adduct of C60 could be identified from these reactions. The previously reported [5,6]-open product of C60 should be reassigned as a [6,6]-closed product

  [60]富勒烯（C 60）与由N-苄基-4-硝基苯甲酰氯/ N-（4-氯苄基）-4-硝基苯甲酰氯和三乙胺生成的腈发生反应，仅得到C 60与[6， 6]封闭式结构。从这些反应中不能鉴定出C 60的[5,6]-开放加合物。先前报告的C 60的[5,6 ]开孔产物应重新分配为[6,6]闭孔产物。
• Reaction of [60]Fullerene with 4-Nitro-<i>N</i>-benzylbenzimidoyl Chloride and Triethylamine: A New Method for the Synthesis of [60]Fullerene-Fused Pyrroline
  作者：Shi-Hui Wu、Guan-Wu Wang、Lian-He Shu、Hou-Ming Wu、Shao-Kai Jiang、Jing-Fei Xu

  DOI：10.1080/00397919708006072

  日期：1997.4

  Abstract Two isomeric [60]fullerene-fused pyrrolines and a derivative of [60]fulleropyrrolidine were obtained from the reaction of [60]fullerene with imidoyl chloride and triethylamine

  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。
• ONYSKO, P. P.;KIM, T. V.;KISELEVA, E. I.;PROKOPENKO, V. P.;SINITSA, A. D., ZH. OBSHCH. XIMII, 60,(1990) N, S. 523-527
  作者：ONYSKO, P. P.、KIM, T. V.、KISELEVA, E. I.、PROKOPENKO, V. P.、SINITSA, A. D.

  DOI：——

  日期：——