4-(Trifluoromethyl)-2-isovalerylpyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(Trifluoromethyl)-2-isovalerylpyridine
• 英文别名: 4-trifluoromethyl-2-isovalerylpyridine；3-Methyl-1-[4-(trifluoromethyl)pyridin-2-yl]butan-1-one；3-methyl-1-[4-(trifluoromethyl)pyridin-2-yl]butan-1-one
• 化学式: C₁₁H₁₂F₃NO
• 分子量: 231.218
• InChiKey: UKSQKOYBHPUUMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(Trifluoromethyl)-2-isovalerylpyridine 以 苯 为溶剂， 生成 1-[4-(三氟甲基)-2-吡啶基]乙酮 、 1-(4-trifluoromethyl-2-pyridyl)-2,2-dimethylcyclopropan-1-ol 、 3-Methyl-1-[4-(trifluoromethyl)pyridin-2-yl]cyclobutan-1-ol
  参考文献：
  名称：

  在4-三氟甲基-2-异戊醛吡啶中由离散的氮和氧三联体介导的氢提取的证据

  摘要：

  辐照1b会导致氮脱氢和形成2b，以及氧引起氢脱氢和3b和4b的形成。斯特恩-沃尔默淬火数据和三重态敏化实验提供的证据表明，这些反应通过介导两个分立Nπ*三重态：羰基氧三重峰，E Ť约70千卡/摩尔，τ〜13纳秒，和氮气三重躺在稍高能量τ〜31 ns。

  DOI：

  10.1016/s0040-4039(00)61682-9
• 作为产物：
  描述：

  4-三氟甲基吡啶 、 sodium 4-methyl-2-oxovalerate 在 ammonium persulfate 、 硫酸 、 silver nitrate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 4-(Trifluoromethyl)-2-isovalerylpyridine
  参考文献：
  名称：

  Substituent Effects on Photochemical Hydrogen Abstraction in 2-Acylpyridines, 2-Acylpyrazines, and 4-Acylpyrimidines

  摘要：

  Stern-Volmer quenching of the photochemistry of 1c indicates that N- and O-abstraction (eqs 1 and 2, respectively) are quenched at different rates (Figure 1). For quenching of 2c k(q) tau is 157 M(-1) and for 3c, 64 M(-1). When 1c is sensitized with triplet sensitizers of increasing E(T), N-abstraction increases (Table 1). These data indicate that N- and O-abstraction in 1c take place from distinguishable triplet states. Survey of Phi(p)'s of ring-substituted ketones 1b-d, 6d, 7a,b,d, 8b, 9b,d, 10b, and 11d demonstrates the effect of substitution on the competition between N- and O-abstraction (Table 2). For methyl- and diacyano-substituted ketones, the results can be understood simply in terms of shifts in E(T) of the n pi* and pi pi* states of the heterocycle. The photochemistry of all these ketones requires consideration of interactions among three triplet states.

  DOI：

  10.1021/jo00087a032

文献信息

• Evidence for hydrogen abstraction mediated by discrete nitrogen and oxygen triplets in 4-trifluoromethyl-2-isovalerylpyridine
  作者：C.Janakiram Rao、William C. Agosta

  DOI：10.1016/s0040-4039(00)61682-9

  日期：1993.10

  Irradiation of 1b leads to abstraction of hydrogen by nitrogen and formation of 2b, as well as abstraction of hydrogen by oxygen and formation of 3b and 4b. Stern-Volmer quenching data and triplet sensitization experiments provide evidence that these reactions are mediated by two discrete nπ* triplet states: a carbonyl oxygen triplet, ET ∼70 kcal/mol, τ ∼13 ns, and a nitrogen triplet lying at somewhat higher

  辐照1b会导致氮脱氢和形成2b，以及氧引起氢脱氢和3b和4b的形成。斯特恩-沃尔默淬火数据和三重态敏化实验提供的证据表明，这些反应通过介导两个分立Nπ*三重态：羰基氧三重峰，E Ť约70千卡/摩尔，τ〜13纳秒，和氮气三重躺在稍高能量τ〜31 ns。
• Substituent Effects on Photochemical Hydrogen Abstraction in 2-Acylpyridines, 2-Acylpyrazines, and 4-Acylpyrimidines
  作者：C. Janakiram Rao、William C. Agosta

  DOI：10.1021/jo00087a032

  日期：1994.4

  Stern-Volmer quenching of the photochemistry of 1c indicates that N- and O-abstraction (eqs 1 and 2, respectively) are quenched at different rates (Figure 1). For quenching of 2c k(q) tau is 157 M(-1) and for 3c, 64 M(-1). When 1c is sensitized with triplet sensitizers of increasing E(T), N-abstraction increases (Table 1). These data indicate that N- and O-abstraction in 1c take place from distinguishable triplet states. Survey of Phi(p)'s of ring-substituted ketones 1b-d, 6d, 7a,b,d, 8b, 9b,d, 10b, and 11d demonstrates the effect of substitution on the competition between N- and O-abstraction (Table 2). For methyl- and diacyano-substituted ketones, the results can be understood simply in terms of shifts in E(T) of the n pi* and pi pi* states of the heterocycle. The photochemistry of all these ketones requires consideration of interactions among three triplet states.