7-(4-nitrophenyl)-3,6-diphenyl-2-thioxo-1,3-diazepane-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 7-(4-nitrophenyl)-3,6-diphenyl-2-thioxo-1,3-diazepane-4-one
• 英文别名: (6R,7S)-7-(4-nitrophenyl)-3,6-diphenyl-2-sulfanylidene-1,3-diazepan-4-one
• 化学式: C₂₃H₁₉N₃O₃S
• 分子量: 417.488
• InChiKey: MTXOWOWCCYPZOW-IFMALSPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 肉桂醛 、 苯基硫脲 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以71%的产率得到7-(4-nitrophenyl)-3,6-diphenyl-2-thioxo-1,3-diazepane-4-one
  参考文献：
  名称：

  Highly Diastereoselective NHC-Catalyzed [4+3] Annulation of Enals, Alde­hydes and N-Phenyl Urea/Thiourea for the Synthesis of Monocyclic trans-1,3-Diazepanes

  摘要：

  N-Heterocyclic carbene catalyzed synthesis of 1,3-diazepanes from ,-unsaturated aldehydes, N-phenyl urea/thiourea and aromatic aldehydes has been developed. The reactive Breslow intermediate, formed by reaction of the enal with the NHC, attacks as a d(3) nucleophile at the 1-arylidene-3-arylurea derivative, which is produced by simple reaction of N-phenyl urea/thiourea with an aromatic aldehyde. The resulting intermediate, on subsequent heterocyclization, forms the product with high yield. The reaction proceeded smoothly with high atom economy, producing a new C-C and a new C-N bond in a one-pot operation.

  DOI：

  10.1055/s-0033-1339894

文献信息

• Highly Diastereoselective NHC-Catalyzed [4+3] Annulation of Enals, Alde­hydes and N-Phenyl Urea/Thiourea for the Synthesis of Monocyclic trans-1,3-Diazepanes
  作者：Ibadur Siddiqui、Anjali Srivastava、Shayna Shamim、Arjita Srivastava、Malik Waseem、Rana Singh

  DOI：10.1055/s-0033-1339894

  日期：——

  N-Heterocyclic carbene catalyzed synthesis of 1,3-diazepanes from ,-unsaturated aldehydes, N-phenyl urea/thiourea and aromatic aldehydes has been developed. The reactive Breslow intermediate, formed by reaction of the enal with the NHC, attacks as a d(3) nucleophile at the 1-arylidene-3-arylurea derivative, which is produced by simple reaction of N-phenyl urea/thiourea with an aromatic aldehyde. The resulting intermediate, on subsequent heterocyclization, forms the product with high yield. The reaction proceeded smoothly with high atom economy, producing a new C-C and a new C-N bond in a one-pot operation.