N-(2-Nitrobenzoyl)-2-azacyclopentanone | 100230-73-7

• 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-(2-Nitrobenzoyl)-2-azacyclopentanone
• 英文别名: N-(2-nitrobenzoyl)-2-pyrrolidone；1-(2-Nitrobenzoyl)pyrrolidin-2-one
• CAS: 100230-73-7
• 化学式: C₁₁H₁₀N₂O₄
• 分子量: 234.211
• InChiKey: MXJHINFPMQLYCL-UHFFFAOYSA-N

物化性质

• 沸点：
  444.5±37.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-Nitrobenzoyl)-2-azacyclopentanone 在 selenium 一氧化碳 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、506.62 kPa 条件下， 反应 10.0h， 以75%的产率得到脱氧鸭嘴花碱酮
  参考文献：
  名称：

  Synthesis of 3,4-dihydroquinazolin-4-one: selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide

  摘要：

  A catalytic synthetic method of 3,4-dihydroquinazolin-4-ones has been developed. When N-(2-nitrobenzoyl)amides were treated with carbon monoxide in the presence of a catalytic amount of selenium, reductive N-heterocyclization of N-(2-nitrobenzoyl)amide efficiently proceeded to give the corresponding 3,4-dihydroquinazolin-4-ones in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00035-7
• 作为产物：
  描述：

  (S)-N-(2-nitrobenzyl)-pyrrolidine-2-carbinol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 以6%的产率得到N-(2-Nitrobenzoyl)-2-azacyclopentanone
  参考文献：
  名称：

  Synthesis and stereochemistry of carbinolamine-containing pyrrolo[1,4]benzodiazepines by reductive cyclization of N-(2-nitrobenzoyl)pyrrolidine-2-carboxaldehydes

  摘要：

  DOI：

  10.1021/jo00355a022

文献信息

• Simple and scalable electrosynthesis of 1<i>H</i>-1-hydroxy-quinazolin-4-ones
  作者：Olesja Koleda、Tobias Prenzel、Johannes Winter、Tomoki Hirohata、María de Jesús Gálvez-Vázquez、Dieter Schollmeyer、Shinsuke Inagi、Edgars Suna、Siegfried R. Waldvogel

  DOI：10.1039/d3sc00266g

  日期：——

  inexpensive and reusable carbon-based electrode materials, an undivided electrochemical setup, and constant current conditions characterise this method. Sulphuric acid is used as a simple supporting electrolyte as well as a catalyst for cyclisation. The broad applicability of this protocol is demonstrated in 27 differently substituted derivatives in high yields of up to 92%. Moreover, mechanistic studies

  阴极合成可以从容易获得的硝基起始材料中可持续地获得 1-羟基-和 1-氧基-喹唑啉-4-酮。该方法具有温和的反应条件、廉价且可重复使用的碳基电极材料、完整的电化学装置和恒定电流条件的特点。硫酸用作简单的支持电解质以及环化催化剂。该方案的广泛适用性在 27 种不同取代的衍生物中得到了证明，产率高达 92%。此外，基于循环伏安法测量的机理研究强调，硝基底物选择性还原为羟胺是关键步骤。克级电解放大 100 倍证明了其与制备应用的相关性。
• Transition-metal complex-catalyzed reductive N-heterocyclization: synthesis of 4(3H)-quinazolinone derivatives from N-(2-nitrobenzoyl)amides
  作者：Motohiro Akazome、Teruyuki Kondo、Yoshihisa Watanabe

  DOI：10.1021/jo00054a008

  日期：1993.1

  Several ruthenium and platinum complexes smoothly catalyze the reductive N-heterocyclization of N-(2-nitrobenzoyl)amides under carbon monoxide pressure to afford the corresponding 4(3H)-quinazolinone derivatives, including some quinazolinone alkaloids, in good yields.
• Synthesis and stereochemistry of carbinolamine-containing pyrrolo[1,4]benzodiazepines by reductive cyclization of N-(2-nitrobenzoyl)pyrrolidine-2-carboxaldehydes
  作者：David E. Thurston、David R. Langley

  DOI：10.1021/jo00355a022

  日期：1986.3
• Synthesis of 3,4-dihydroquinazolin-4-one: selenium-catalyzed reductive N-heterocyclization of N-(2-nitrobenzoyl)amides with carbon monoxide
  作者：Yutaka Nishiyama、Masaharu Hirose、Wataru Kitagaito、Noboru Sonoda

  DOI：10.1016/s0040-4039(02)00035-7

  日期：2002.3

  A catalytic synthetic method of 3,4-dihydroquinazolin-4-ones has been developed. When N-(2-nitrobenzoyl)amides were treated with carbon monoxide in the presence of a catalytic amount of selenium, reductive N-heterocyclization of N-(2-nitrobenzoyl)amide efficiently proceeded to give the corresponding 3,4-dihydroquinazolin-4-ones in moderate to good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.