5-hydroxy-6-[(4-nitrophenyl)sulfanyl]-1-(pyrrolidin-1-yl)hexan-1-one | 1454693-25-4

• 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: 5-hydroxy-6-[(4-nitrophenyl)sulfanyl]-1-(pyrrolidin-1-yl)hexan-1-one
• CAS: 1454693-25-4
• 化学式: C₁₆H₂₂N₂O₄S
• 分子量: 338.428
• InChiKey: GISUPERUIFTMIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-6-[(4-nitrophenyl)sulfanyl]-1-(pyrrolidin-1-yl)hexan-1-one 在 oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以95%的产率得到5-hydroxy-6-[(4-nitrophenyl)sulfonyl]-1-(pyrrolidin-1-yl)hexan-1-one
  参考文献：
  名称：

  Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: IV. Cyclosulfenylation of 5-hexenoic acid amides and nucleophilic cleavage of reaction products

  摘要：

  Anilides of 5-hexenoic acid react with arylsulfenyl chlorides in nitromethane in the presence of lithium perchlorate affording products of electrophilic cyclization, N-{6-[(arylsulfanyl)methyl]tetrahydro-2H-pyran-2-ylidene}anilinium perchlorates. The treatment of the latter with sodium acetate or secondary cycloalkylamines in the presence of water results in the opening of the tetrahydropyran ring and provides anilides or cycloalkylamides of 6-arylsulfanyl-5-hydroxyhexanoic acid.

  DOI：

  10.1134/s1070428013080125
• 作为产物：
  描述：

  N-phenylhex-5-enamide 在 lithium perchlorate 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 生成 5-hydroxy-6-[(4-nitrophenyl)sulfanyl]-1-(pyrrolidin-1-yl)hexan-1-one
  参考文献：
  名称：

  Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: IV. Cyclosulfenylation of 5-hexenoic acid amides and nucleophilic cleavage of reaction products

  摘要：

  Anilides of 5-hexenoic acid react with arylsulfenyl chlorides in nitromethane in the presence of lithium perchlorate affording products of electrophilic cyclization, N-{6-[(arylsulfanyl)methyl]tetrahydro-2H-pyran-2-ylidene}anilinium perchlorates. The treatment of the latter with sodium acetate or secondary cycloalkylamines in the presence of water results in the opening of the tetrahydropyran ring and provides anilides or cycloalkylamides of 6-arylsulfanyl-5-hydroxyhexanoic acid.

  DOI：

  10.1134/s1070428013080125