4-hydroxy-3-phenylsulfanyl-1-tosylimino-1H-2-benzopyran | 169513-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-3-phenylsulfanyl-1-tosylimino-1H-2-benzopyran
• 英文别名: N-(4-hydroxy-3-phenylsulfanylisochromen-1-ylidene)-4-methylbenzenesulfonamide
• CAS: 169513-54-6
• 化学式: C₂₂H₁₇NO₄S₂
• 分子量: 423.513
• InChiKey: HJCDOCKHBUMHHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-hydroxy-3-phenylsulfanyl-1-tosylimino-1H-2-benzopyran 反应 1.0h， 以83%的产率得到4-acetoxy-3-phenylsulfanyl-1-tosylimino-1H-2-benzopyran
  参考文献：
  名称：

  Reactions of tosyl azide with 2-phenoxy- and 2-phenylsulfanyl-2,3-dihydro-1H-indane-1,3-dione. Unexpected reactivity of intermediate 4-acyl-5-hydroxy-1-tosyltriazolines

  摘要：

  The reaction of tosyl azide 1 with 2-phenoxy-2;3-dihydro-1H-indane-1,3-dione 2c, carried out in hexamethylphosphoramide (HMPA) or in diethyl ether in the presence of triethylamine, fails to afford the expected diazo transfer product, i. e. the diazoacetophenone 3c (3c'), but instead leads to the dimeric indanedione 7 the formation of which is primarily ascribable to preferential fragmentation of the transient hydroxytriazoline 4c to give zwitterion 9c and dinitrogen. Under comparable conditions, tosyl azide 1 and 2-phenylsulfanyl-2,3-dihydro-1H-indane-1,3-dione 2d in HMPA gives the ring-expanded hydroxybenzopyran 15, the formation of which is similarly ascribed to preferential fragmentation of the corresponding 4,5-dihydro-1H-triazole 4d to give zwitterion 9d. However, analogous reaction of the dione 2d in THF, in the presence of triethylamine, affords 2-diazo-2,3-dihydro-1H-indane-1,3-dione along with diphenyl disulfide, toluene-p-sulfonamide and phenyl toluene-4-thiosulfonate. These latter-products are believed to arise from ready decomposition of the 4,5-dihydro-1 H-triazole 4d precursor, i.e the triazenyl anion 13. X-Ray crystal structure analyses of compound 7 and the acetoxybenzopyran 17 are also reported.

  DOI：

  10.1039/p19950001381
• 作为产物：
  描述：

  N-methyl-4-nitro-N-(phenylthio)benzenamine 在 sodium hydride 作用下， 以 六甲基磷酰三胺 、 乙腈 为溶剂， 反应 26.0h， 生成 4-hydroxy-3-phenylsulfanyl-1-tosylimino-1H-2-benzopyran
  参考文献：
  名称：

  Reactions of tosyl azide with 2-phenoxy- and 2-phenylsulfanyl-2,3-dihydro-1H-indane-1,3-dione. Unexpected reactivity of intermediate 4-acyl-5-hydroxy-1-tosyltriazolines

  摘要：

  The reaction of tosyl azide 1 with 2-phenoxy-2;3-dihydro-1H-indane-1,3-dione 2c, carried out in hexamethylphosphoramide (HMPA) or in diethyl ether in the presence of triethylamine, fails to afford the expected diazo transfer product, i. e. the diazoacetophenone 3c (3c'), but instead leads to the dimeric indanedione 7 the formation of which is primarily ascribable to preferential fragmentation of the transient hydroxytriazoline 4c to give zwitterion 9c and dinitrogen. Under comparable conditions, tosyl azide 1 and 2-phenylsulfanyl-2,3-dihydro-1H-indane-1,3-dione 2d in HMPA gives the ring-expanded hydroxybenzopyran 15, the formation of which is similarly ascribed to preferential fragmentation of the corresponding 4,5-dihydro-1H-triazole 4d to give zwitterion 9d. However, analogous reaction of the dione 2d in THF, in the presence of triethylamine, affords 2-diazo-2,3-dihydro-1H-indane-1,3-dione along with diphenyl disulfide, toluene-p-sulfonamide and phenyl toluene-4-thiosulfonate. These latter-products are believed to arise from ready decomposition of the 4,5-dihydro-1 H-triazole 4d precursor, i.e the triazenyl anion 13. X-Ray crystal structure analyses of compound 7 and the acetoxybenzopyran 17 are also reported.

  DOI：

  10.1039/p19950001381