5-(4-chlorobenzoyl)-N-(2-nitrobenzyl)-2-pyrrolidinone | 1242192-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(4-chlorobenzoyl)-N-(2-nitrobenzyl)-2-pyrrolidinone
• CAS: 1242192-90-0
• 化学式: C₁₈H₁₅ClN₂O₄
• 分子量: 358.781
• InChiKey: VGEUMGNYZSDXRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.52
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(4-chlorobenzoyl)-N-(2-nitrobenzyl)-2-pyrrolidinone 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 生成 syn-11-(4-chlorophenyl)-1,2,5,10,11,11a-hexahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-one 、 anti-11-(4-chlorophenyl)-1,2,5,10,11,11a-hexahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-3-one
  参考文献：
  名称：

  A versatile PIFA-mediated approach to structurally diverse pyrrolo(benzo)diazepines from linear alkynylamides

  摘要：

  The addition of the hypervalent iodine reagent PIFA [phenyliodine(III) bis(trifluoroacetate)] to a series of properly substituted N-(3-aminopropyl)alkynylamides results in the efficient formation of a functionalized 5-aroyl-2-pyrrolidinone skeleton. By proper manipulations of the N(1)-substituents, through consecutive deprotection and/or reductive amination steps, a second cyclization process occurs yielding the target heterocycles. As it will be disclosed, the overall process is open to structural modifications that gives rise to a series of pyrrolo(benzo)diazepine derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.080
• 作为产物：
  描述：

  5-(4-chlorophenyl)-N-(2-nitrobenzyl)-4-pentynamide 在 [双(三氟乙酰氧基)碘]苯 、 水 、 sodium carbonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以57%的产率得到5-(4-chlorobenzoyl)-N-(2-nitrobenzyl)-2-pyrrolidinone
  参考文献：
  名称：

  A versatile PIFA-mediated approach to structurally diverse pyrrolo(benzo)diazepines from linear alkynylamides

  摘要：

  The addition of the hypervalent iodine reagent PIFA [phenyliodine(III) bis(trifluoroacetate)] to a series of properly substituted N-(3-aminopropyl)alkynylamides results in the efficient formation of a functionalized 5-aroyl-2-pyrrolidinone skeleton. By proper manipulations of the N(1)-substituents, through consecutive deprotection and/or reductive amination steps, a second cyclization process occurs yielding the target heterocycles. As it will be disclosed, the overall process is open to structural modifications that gives rise to a series of pyrrolo(benzo)diazepine derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.080