4-(prop-1-en-1-yl)pyridine | 17618-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(prop-1-en-1-yl)pyridine
• 英文别名: 4-Propenylpyridine；4-prop-1-enylpyridine
• CAS: 17618-95-0
• 化学式: C₈H₉N
• 分子量: 119.166
• InChiKey: PWZRAFPNQSAEBD-UHFFFAOYSA-N

物化性质

• 沸点：
  197.2±9.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(prop-1-en-1-yl)pyridine 在 乙醇 、 sodium 作用下， 生成 4-正丙基哌啶
  参考文献：
  名称：

  Ahrens, Chemische Berichte, 1905, vol. 38, p. 159

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(pyridin-4-yl)propan-1-ol 在 PPA 作用下， 反应 0.25h， 生成 4-(prop-1-en-1-yl)pyridine
  参考文献：
  名称：

  Synthesis of pyridines from alcohols in the system 1,3,5-triazine-polyphosphoric acid

  摘要：

  DOI：

  10.1134/s1070428009090206

文献信息

• Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketones <i>via</i> N₂H₄ mediated deoxygenative couplings
  作者：Leiyang Lv、Chao-Jun Li

  DOI：10.1039/d0sc06586b

  日期：——

  aldehyde/ketones via N2H4 mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their

  醛/酮的 Umpolung（极性反转）策略通过使用亲电试剂和脱氧官能化进行转化，极大地拓宽了羰基化学。在此，我们报道了第一次钌催化的乙烯基吡啶与天然丰富的芳香族和脂肪族醛/酮通过N 2 H 4进行的 β-选择性烷基化介导的脱氧偶联。与羰基到醇的单电子 umpolung 相比，这种双电子 umpolung 策略实现了还原脱氧目标，不仅适用于广泛的 2/4-烯烃取代的吡啶的区域选择性烷基化，而且还可以应对具有挑战性的 3 -乙烯基和空间嵌入的内部吡啶以及它们类似的杂环结构。
• Facile and highly selective silylation of vinylpyridines at the β-olefinic carbon by magnesium-promoted reduction
  作者：Tianyuan Zhang、Zeyu Zhang、Yutaro Nishiyama、Hirofumi Maekawa

  DOI：10.1016/j.tet.2016.03.042

  日期：2016.5

  Magnesium-promoted reductive silylation of 2- and 4-vinylpyridines with chlorotrialkylsilanes in N-methylpyrrolidinone at room temperature led to the selective formation of a variety of the corresponding β-mono-silylated compounds at the terminal carbon atom in good to excellent yields, whereas silylation of 3-vinylpyridine under the same reduction conditions failed to give a complex mixture of silylated

  在室温下，镁在N-甲基吡咯烷酮中用氯三烷基硅烷促进2-和4-乙烯基吡啶的还原甲硅烷基化，从而导致在末端碳原子上选择性形成各种相应的β-单甲硅烷基化化合物，而收率很好，反而更好。在相同的还原条件下使3-乙烯基吡啶甲硅烷基化不能得到甲硅烷基化化合物的复杂混合物。2-或4-乙烯基吡啶与3-乙烯基吡啶之间的结果差异归因于通过与吡啶的氮原子的共振对反应中间体的稳定作用。
• Photosensitized [4+2]‐ and [2+2]‐Cycloaddition Reactions of <i>N</i>‐Sulfonylimines
  作者：Wang Wang、M. Kevin Brown

  DOI：10.1002/anie.202305622

  日期：2023.8.7

  Dearomative [4+2]-cycloadditions and azetidine-forming [2+2] cycloadditions (aza-Paternó-Büchi reactions) of sulfonylimines are presented. The divergent reactivity was achieved though substrate modulation. In both cases, the reactions lead to the synthesis of complex polycyclic scaffolds from simple components. The mechanistic details and the utility of the products are described.

  提出了磺酰亚胺的脱芳香[4+2]-环加成和氮杂环丁烷形成[2+2]环加成（氮杂-Paternó-Büchi 反应）。通过底物调节实现了不同的反应性。在这两种情况下，反应都会导致从简单组分合成复杂的多环支架。描述了产品的机械细节和实用性。
• Ishikura, Minoru; Kamada, Machiko; Ohta, Tsukasa, Heterocycles, 1984, vol. 22, # 11, p. 2475 - 2478
  作者：Ishikura, Minoru、Kamada, Machiko、Ohta, Tsukasa、Terashima, Masanao

  DOI：——

  日期：——
• Selective introduction of a trifluoroacetyl group onto 4-vinylpyridines through magnesium-promoted reduction
  作者：Hirofumi Maekawa、Yutaro Nishiyama

  DOI：10.1016/j.tet.2015.07.046

  日期：2015.9

  Magnesium-promoted reductive coupling of 4-vinylpyridines and ethyl trifluoroacetate in the presence of chlorotrimethylsilane in N-methyl-2-pyrrolidone resulted in selective formation of the tri-fluoroacetylated compounds at the beta-olefinic carbon of the pyridine ring, the electron deficient carbon in good yields. In particular, 4-vinylpyridine with an aromatic ring at the beta-olefinic position of the pyridine ring gave higher yield of the trifluoroacetylated compound. The nitrogen atom of the pyridine ring may play an important role in the regioselectivity of the product. (C) 2015 Elsevier Ltd. All rights reserved.