4,5-Dimethyl-1-(toluene-4-sulfonyl)-1,5-dihydro-pyrrol-2-one | 138816-55-4

• 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: 4,5-Dimethyl-1-(toluene-4-sulfonyl)-1,5-dihydro-pyrrol-2-one
• CAS: 138816-55-4
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: PRVKZOWPJYJROV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,5-Dimethyl-1-(toluene-4-sulfonyl)-1,5-dihydro-pyrrol-2-one 在 platinum(IV) oxide 氢气 、 sodium naphthalenide 作用下， 以 乙二醇二甲醚 、 溶剂黄146 为溶剂， 反应 28.5h， 生成 (4R,5S)-4,5-Dimethyl-pyrrolidin-2-one
  参考文献：
  名称：

  Transition metal catalyzed radical cyclization: new preparative route to .gamma.-lactams from allylic alcohols via the [3.3]-sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium-catalyzed cyclization of N-allyltrichloroacetamides

  摘要：

  A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated gamma-lactams from allylic alcohols. No delta-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.

  DOI：

  10.1021/jo00032a016
• 作为产物：
  描述：

  1-tosyl-3-(phenylselenyl)-5-methyl-2-pyrrolidinone 在 sodium periodate 、 copper(l) iodide 、 苯基溴化硒 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 3.17h， 生成 4,5-Dimethyl-1-(toluene-4-sulfonyl)-1,5-dihydro-pyrrol-2-one
  参考文献：
  名称：

  Transition metal catalyzed radical cyclization: new preparative route to .gamma.-lactams from allylic alcohols via the [3.3]-sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium-catalyzed cyclization of N-allyltrichloroacetamides

  摘要：

  A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated gamma-lactams from allylic alcohols. No delta-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.

  DOI：

  10.1021/jo00032a016