1-(4-bromobenzyl)-3-chloro-4-(3-chloro-2-nitrophenyl)pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-bromobenzyl)-3-chloro-4-(3-chloro-2-nitrophenyl)pyrrole
• 英文别名: 1-[(4-Bromophenyl)methyl]-3-chloro-4-(3-chloro-2-nitrophenyl)pyrrole
• 化学式: C₁₇H₁₁BrCl₂N₂O₂
• 分子量: 426.097
• InChiKey: NRDQLNFMTHDLCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)-3-chloro-4-(3-chloro-2-nitrophenyl)pyrrole 以 水 、 乙腈 为溶剂， 反应 2.0h， 以13%的产率得到1'-[(4-bromophenyl)methyl]-4',7-dichlorospiro[1H-2,1-benzoxazole-3,3'-pyrrole]-2'-one
  参考文献：
  名称：

  Novel Photodegradation of the Antifungal Antibiotic Pyrrolnitrin in Anhydrous and Aqueous Aprotic Solvents

  摘要：

  The UV irradiation of pyrrolnitrin (1a), which is an antibiotic clinically useful against dermatophytosis and possesses a unique 2-(pyrrol-3-yl)nitrobenzene moiety in the molecule, in an anhydrous aprotic solvent resulted in the exclusive formation of transient 7,4'-dichlorospiro[1,3-dihydrobenzo-(c)isoxazole-3,3'-pyrrolin-2'-one] (2a) via the intramolecular oxidation of the juxtaposed pyrrole ring by the triplet-excited nitro group. The irradiation in an aqueous aprotic solvent, however, allowed the concurrent occurrence of intramolecular cyclization by the singlet-excited nitro group in 1a and the hydroxylation at the 2-position of the pyrrole ring by water to afford 3,7-dichloro-8-hydroxy-8,8a-dihydropyrrolo[2,3-b]indol-2-one (3a), accompanied by the formation of 2a. Elongation of the irradiation time in these photoreactions caused a rapid consumption of the products, 2a and 3a, to give undetermined polar polymeric products. The present results indicate that the photodegradation of 1a is significantly influenced by the presence of water in the reaction media and by the nature of its excited state. Thus, the loss of the antifungal activities by the photosensitive antibiotic 1a was chemically proved.

  DOI：

  10.1021/jo010619z
• 作为产物：
  描述：

  硝吡咯菌素 、 对溴溴苄 在 lithium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到1-(4-bromobenzyl)-3-chloro-4-(3-chloro-2-nitrophenyl)pyrrole
  参考文献：
  名称：

  Novel Photodegradation of the Antifungal Antibiotic Pyrrolnitrin in Anhydrous and Aqueous Aprotic Solvents

  摘要：

  The UV irradiation of pyrrolnitrin (1a), which is an antibiotic clinically useful against dermatophytosis and possesses a unique 2-(pyrrol-3-yl)nitrobenzene moiety in the molecule, in an anhydrous aprotic solvent resulted in the exclusive formation of transient 7,4'-dichlorospiro[1,3-dihydrobenzo-(c)isoxazole-3,3'-pyrrolin-2'-one] (2a) via the intramolecular oxidation of the juxtaposed pyrrole ring by the triplet-excited nitro group. The irradiation in an aqueous aprotic solvent, however, allowed the concurrent occurrence of intramolecular cyclization by the singlet-excited nitro group in 1a and the hydroxylation at the 2-position of the pyrrole ring by water to afford 3,7-dichloro-8-hydroxy-8,8a-dihydropyrrolo[2,3-b]indol-2-one (3a), accompanied by the formation of 2a. Elongation of the irradiation time in these photoreactions caused a rapid consumption of the products, 2a and 3a, to give undetermined polar polymeric products. The present results indicate that the photodegradation of 1a is significantly influenced by the presence of water in the reaction media and by the nature of its excited state. Thus, the loss of the antifungal activities by the photosensitive antibiotic 1a was chemically proved.

  DOI：

  10.1021/jo010619z

文献信息

• Novel Photodegradation of the Antifungal Antibiotic Pyrrolnitrin in Anhydrous and Aqueous Aprotic Solvents
  作者：Magoichi Sako、Toshiyuki Kihara、Mihoko Tanisaki、Yoshifumi Maki、Akira Miyamae、Toshio Azuma、Shigetaka Kohda、Takashi Masugi

  DOI：10.1021/jo010619z

  日期：2002.2.1

  The UV irradiation of pyrrolnitrin (1a), which is an antibiotic clinically useful against dermatophytosis and possesses a unique 2-(pyrrol-3-yl)nitrobenzene moiety in the molecule, in an anhydrous aprotic solvent resulted in the exclusive formation of transient 7,4'-dichlorospiro[1,3-dihydrobenzo-(c)isoxazole-3,3'-pyrrolin-2'-one] (2a) via the intramolecular oxidation of the juxtaposed pyrrole ring by the triplet-excited nitro group. The irradiation in an aqueous aprotic solvent, however, allowed the concurrent occurrence of intramolecular cyclization by the singlet-excited nitro group in 1a and the hydroxylation at the 2-position of the pyrrole ring by water to afford 3,7-dichloro-8-hydroxy-8,8a-dihydropyrrolo[2,3-b]indol-2-one (3a), accompanied by the formation of 2a. Elongation of the irradiation time in these photoreactions caused a rapid consumption of the products, 2a and 3a, to give undetermined polar polymeric products. The present results indicate that the photodegradation of 1a is significantly influenced by the presence of water in the reaction media and by the nature of its excited state. Thus, the loss of the antifungal activities by the photosensitive antibiotic 1a was chemically proved.