1-pentyl 4-nitrobenzenesulfinate

• 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: 1-pentyl 4-nitrobenzenesulfinate
• 英文别名: Pentyl 4-nitrobenzenesulfinate；pentyl 4-nitrobenzenesulfinate
• 化学式: C₁₁H₁₅NO₄S
• 分子量: 257.31
• InChiKey: BPTWIPKXQWIMQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  91.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯亚磺酰氯 在 氧气 、 三乙胺 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 1-pentyl 4-nitrobenzenesulfinate
  参考文献：
  名称：

  Self-induced, photochemical, singlet-oxygen oxidation of 4-nitrobenzenesulfenates to 4-nitrobenzenesulfinates

  摘要：

  It has been previously reported that the photo-induced homolytic dissociation of homoallyl an 4-nitrobenzenesulfenates, followed by beta-scission of the alkoxy radicals to allyl and alkyl radicals leads to the formation of sulfides. In the presence of dioxygen the alkyl sulfenates undergo oxidation to the corresponding alkyl sulfinates. The results of theoretical studies suggest that the absorption of the photon results in the excitation of an electron from the pi-type sulfur nonbonded-pair MO (the HOMO) to a pi* MO of the aromatic ring (the LUMO). Quenching studies indicate that a triplet excited state is ultimately formed which then reacts with triplet dioxygen to form singlet dioxygen, which can be trapped with 1,3-cyclohexadiene, which then reacts with ground-state sulfenate.

  DOI：

  10.1021/jo00067a052

文献信息

• Self-induced, photochemical, singlet-oxygen oxidation of 4-nitrobenzenesulfenates to 4-nitrobenzenesulfinates
  作者：Daniel J. Pasto、Francois Cottard、Sandra Horgan

  DOI：10.1021/jo00067a052

  日期：1993.7

  It has been previously reported that the photo-induced homolytic dissociation of homoallyl an 4-nitrobenzenesulfenates, followed by beta-scission of the alkoxy radicals to allyl and alkyl radicals leads to the formation of sulfides. In the presence of dioxygen the alkyl sulfenates undergo oxidation to the corresponding alkyl sulfinates. The results of theoretical studies suggest that the absorption of the photon results in the excitation of an electron from the pi-type sulfur nonbonded-pair MO (the HOMO) to a pi* MO of the aromatic ring (the LUMO). Quenching studies indicate that a triplet excited state is ultimately formed which then reacts with triplet dioxygen to form singlet dioxygen, which can be trapped with 1,3-cyclohexadiene, which then reacts with ground-state sulfenate.