1-(4-Hydroxypentyl)-3-methylcyclopent-2-ene | 150668-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Hydroxypentyl)-3-methylcyclopent-2-ene
• 英文别名: 5-(3-Methylcyclopent-2-en-1-yl)pentan-2-ol
• CAS: 150668-02-3
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: OWKQTJSKOLPCKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-Hydroxypentyl)-3-methylcyclopent-2-ene 在 联苯 、 9,10-二氰基蒽 作用下， 以 乙腈 为溶剂， 生成 2,7-Dimethyl-6-oxaspiro<4.5>decane 、 (R^*,S^*)-2,7-Dimethyl-6-oxaspiro<4.5>dec-1-ene 、 (R^*,R^*)-2,7-Dimethyl-6-oxaspiro<4.5>dec-1-ene
  参考文献：
  名称：

  Denitrogenation of bicyclic azoalkanes through photosensitized electron transfer: generation and intramolecular trapping of radical cations

  摘要：

  To elucidate the intermediates that intervene in the denitrogenation of bicyclic azoalkanes by photosensitized electron transfer (PET), the 2,3-diazabicyclo[2.2.1]hept-2-ene (DBH) derivative 1b was synthesized, and its PET reactions were examined. With triphenylpyrylium tetrafluoroborate (TPT) or 9,10-dicyanoanthracene (DCA) as sensitizers and biphenyl as cosensitizer, the azoalkane lb gave through intramolecular cyclization the spiro ethers 5 and 6 as trapping products, in addition to the bicyclopentane 2b and the cyclopentenes 3b,b', the latter as rearrangement products. Comparison with 1,4-dimethyl-DBH (1c) revealed that trapping of a 1,3-diyl radical cation as the major pathway is unlikely. PET experiments with the regioisomeric cyclopentenes 3b,b', which both led to the spiro ether 5, imply the involvement of the allyl cation 3b(-H)+ as the decisive intermediate in the nucleophilic trapping reactions. Comparison of the PET chemistry of the azoalkane lb and the corresponding bicyclopentane 2b gave further insight into the mechanism of denitrogenation of azoalkanes through single electron transfer. The latter results lend additional support for the involvement of the diazenyl radical cation 1.+, which to date has escaped direct detection.

  DOI：

  10.1021/jo00072a009
• 作为产物：
  描述：

  1-(4-Hydroxypentyl)-4-methyl-2,3-diazabicyclo<2.2.1>hept-2-ene 在 联苯 、 9,10-二氰基蒽 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 2,7-Dimethyl-6-oxaspiro<4.5>decane 、 1-(4-Hydroxypentyl)-3-methylcyclopent-2-ene 、 (R^*,S^*)-2,7-Dimethyl-6-oxaspiro<4.5>dec-1-ene 、 (R^*,R^*)-2,7-Dimethyl-6-oxaspiro<4.5>dec-1-ene
  参考文献：
  名称：

  Denitrogenation of bicyclic azoalkanes through photosensitized electron transfer: generation and intramolecular trapping of radical cations

  摘要：

  To elucidate the intermediates that intervene in the denitrogenation of bicyclic azoalkanes by photosensitized electron transfer (PET), the 2,3-diazabicyclo[2.2.1]hept-2-ene (DBH) derivative 1b was synthesized, and its PET reactions were examined. With triphenylpyrylium tetrafluoroborate (TPT) or 9,10-dicyanoanthracene (DCA) as sensitizers and biphenyl as cosensitizer, the azoalkane lb gave through intramolecular cyclization the spiro ethers 5 and 6 as trapping products, in addition to the bicyclopentane 2b and the cyclopentenes 3b,b', the latter as rearrangement products. Comparison with 1,4-dimethyl-DBH (1c) revealed that trapping of a 1,3-diyl radical cation as the major pathway is unlikely. PET experiments with the regioisomeric cyclopentenes 3b,b', which both led to the spiro ether 5, imply the involvement of the allyl cation 3b(-H)+ as the decisive intermediate in the nucleophilic trapping reactions. Comparison of the PET chemistry of the azoalkane lb and the corresponding bicyclopentane 2b gave further insight into the mechanism of denitrogenation of azoalkanes through single electron transfer. The latter results lend additional support for the involvement of the diazenyl radical cation 1.+, which to date has escaped direct detection.

  DOI：

  10.1021/jo00072a009

文献信息

• Denitrogenation of bicyclic azoalkanes through photosensitized electron transfer: generation and intramolecular trapping of radical cations
  作者：Waldemar Adam、Juergen Sendelbach

  DOI：10.1021/jo00072a009

  日期：1993.9

  To elucidate the intermediates that intervene in the denitrogenation of bicyclic azoalkanes by photosensitized electron transfer (PET), the 2,3-diazabicyclo[2.2.1]hept-2-ene (DBH) derivative 1b was synthesized, and its PET reactions were examined. With triphenylpyrylium tetrafluoroborate (TPT) or 9,10-dicyanoanthracene (DCA) as sensitizers and biphenyl as cosensitizer, the azoalkane lb gave through intramolecular cyclization the spiro ethers 5 and 6 as trapping products, in addition to the bicyclopentane 2b and the cyclopentenes 3b,b', the latter as rearrangement products. Comparison with 1,4-dimethyl-DBH (1c) revealed that trapping of a 1,3-diyl radical cation as the major pathway is unlikely. PET experiments with the regioisomeric cyclopentenes 3b,b', which both led to the spiro ether 5, imply the involvement of the allyl cation 3b(-H)+ as the decisive intermediate in the nucleophilic trapping reactions. Comparison of the PET chemistry of the azoalkane lb and the corresponding bicyclopentane 2b gave further insight into the mechanism of denitrogenation of azoalkanes through single electron transfer. The latter results lend additional support for the involvement of the diazenyl radical cation 1.+, which to date has escaped direct detection.