5-Phenyl-6-(toluene-4-sulfonyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyridazine | 187850-59-5

• 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-Phenyl-6-(toluene-4-sulfonyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyridazine
• CAS: 187850-59-5
• 化学式: C₁₉H₁₉N₃O₂S
• 分子量: 353.445
• InChiKey: TVRSWVUPDXRTEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.13
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-Phenyl-6-(toluene-4-sulfonyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyridazine 在 dimethyl azodicarboxylate 作用下， 生成 5-Phenyl-6-(toluene-4-sulfonyl)-4,6-dihydro-1H-pyrrolo[3,4-d]pyridazine
  参考文献：
  名称：

  Triplet Species from Dihydropyrrolo[3,4-d]pyridazines, the Diazene Precursors of N-Arenesulfonyl-3,4-dimethylenepyrroles

  摘要：

  In contrast to the photolyses of N-methyl- or N-pivaloylpyrrolo[3,4]dihydropyridazines in low-temperature matrices, which give the blue, ESR-inactive singlet 3,4-dimethylenepyrrole biradical at all wavelengths, the photolyses of the N-arenesulfonyl derivatives in this series are strongly wavelength-dependent. In three separate instances, both singlet and triplet N-arenesulfonyl-3,4-dimethylenepyrrole biradicals have been observed. In each case, one or two other triplets are seen by ESR spectroscopy after irradiation under special conditions, These are tentatively assigned conformationally isomeric diazenyl biradical structures. The possible origins of the slow intersystem crossing rates for singlet-triplet interconversions in N-arenesulfonyl-3,4-dimethylenepyrrole biradicals are examined. Near-zero ionic character of the singlet wave function is considered to be a less likely cause than conformational control of the spin state. The latter circumstance would require that intersystem crossing be coupled to conformational change, which can be very slow at low temperatures. The zero-field splittings determined from the ESR spectra of N-tosyl-3,4-dimethylenepyrrole biradical are found to be temperature-dependent, which could be caused by librations and/or internal rotational (conformational) motions of the biradical in the matrix.

  DOI：

  10.1021/ja963114c
• 作为产物：
  描述：

  5-Phenyl-6-(toluene-4-sulfonyl)-4,6-dihydro-1H-pyrrolo[3,4-d]pyridazine-2,3-dicarboxylic acid di-tert-butyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 5-Phenyl-6-(toluene-4-sulfonyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyridazine
  参考文献：
  名称：

  Triplet Species from Dihydropyrrolo[3,4-d]pyridazines, the Diazene Precursors of N-Arenesulfonyl-3,4-dimethylenepyrroles

  摘要：

  In contrast to the photolyses of N-methyl- or N-pivaloylpyrrolo[3,4]dihydropyridazines in low-temperature matrices, which give the blue, ESR-inactive singlet 3,4-dimethylenepyrrole biradical at all wavelengths, the photolyses of the N-arenesulfonyl derivatives in this series are strongly wavelength-dependent. In three separate instances, both singlet and triplet N-arenesulfonyl-3,4-dimethylenepyrrole biradicals have been observed. In each case, one or two other triplets are seen by ESR spectroscopy after irradiation under special conditions, These are tentatively assigned conformationally isomeric diazenyl biradical structures. The possible origins of the slow intersystem crossing rates for singlet-triplet interconversions in N-arenesulfonyl-3,4-dimethylenepyrrole biradicals are examined. Near-zero ionic character of the singlet wave function is considered to be a less likely cause than conformational control of the spin state. The latter circumstance would require that intersystem crossing be coupled to conformational change, which can be very slow at low temperatures. The zero-field splittings determined from the ESR spectra of N-tosyl-3,4-dimethylenepyrrole biradical are found to be temperature-dependent, which could be caused by librations and/or internal rotational (conformational) motions of the biradical in the matrix.

  DOI：

  10.1021/ja963114c