2-(pyridin-4-yl)pent-4-en-2-ol | 219531-26-7

• 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: 2-(pyridin-4-yl)pent-4-en-2-ol
• 英文别名: 2-Pyridin-4-ylpent-4-en-2-ol
• CAS: 219531-26-7
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: KCPVNBQRFBDCQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,12-二溴十二烷 、 2-(pyridin-4-yl)pent-4-en-2-ol 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Kinetics of the Self-Assembly of α-Cyclodextrin [2]Pseudorotaxanes with 1,12-Bis(4-(α-alkyl-α-methylmethanol)pyridinium)dodecane Dications in Aqueous Solution

  摘要：

  The kinetics and thermodynamics of the self-assembly of a series of [2]pseudorotaxanes comprised of alpha-cyclodextrin (alpha-CD) and racemic 1,12-bis(4-(alpha-alkyl-alpha-methylmethanol)pyridinium)dodecane dications (L(CH2)(12)L2+) in aqueous;solutions have been investigated using H-1 NMR spectroscopy. The mechanism of assembly involves inclusion of the alpha-methyl-alpha-alkylmethanol substituent groups (-C(CH3)(OH)R, where R = Me, Et, Pr, Bu, allyl, and 4-butenyl) by alpha-CD, followed by a rate-determining passage of the cyclodextrin over the pyridinium group onto the dodecamethylene chain. Dicationic threads containing end groups with R = Ph or i-Pr or where L = 4-(alpha,alpha-diethylmethanol)pyridinium did not form alpha-cyclodextrin pseudorotaxanes, even after prolonged heating. The trends in the rate and activation parameters may be related to the size, shape, and hydrophobicity of the alkyl substituents and are compared with several other systems from the literature. An increase in the length and hydrophobicity of the alkyl group increases the strength of end group inclusion and decreases the rate of threading. In addition, the presence of unsaturation in the alkyl substituent (allyl vs propyl and 4-butenyl vs butyl) results in an increase in the threading rate constant.

  DOI：

  10.1021/jo9808775
• 作为产物：
  描述：

  4-乙酰吡啶 、 烯丙基溴化镁 以 乙醚 为溶剂， 反应 1.0h， 生成 2-(pyridin-4-yl)pent-4-en-2-ol
  参考文献：
  名称：

  Kinetics of the Self-Assembly of α-Cyclodextrin [2]Pseudorotaxanes with 1,12-Bis(4-(α-alkyl-α-methylmethanol)pyridinium)dodecane Dications in Aqueous Solution

  摘要：

  The kinetics and thermodynamics of the self-assembly of a series of [2]pseudorotaxanes comprised of alpha-cyclodextrin (alpha-CD) and racemic 1,12-bis(4-(alpha-alkyl-alpha-methylmethanol)pyridinium)dodecane dications (L(CH2)(12)L2+) in aqueous;solutions have been investigated using H-1 NMR spectroscopy. The mechanism of assembly involves inclusion of the alpha-methyl-alpha-alkylmethanol substituent groups (-C(CH3)(OH)R, where R = Me, Et, Pr, Bu, allyl, and 4-butenyl) by alpha-CD, followed by a rate-determining passage of the cyclodextrin over the pyridinium group onto the dodecamethylene chain. Dicationic threads containing end groups with R = Ph or i-Pr or where L = 4-(alpha,alpha-diethylmethanol)pyridinium did not form alpha-cyclodextrin pseudorotaxanes, even after prolonged heating. The trends in the rate and activation parameters may be related to the size, shape, and hydrophobicity of the alkyl substituents and are compared with several other systems from the literature. An increase in the length and hydrophobicity of the alkyl group increases the strength of end group inclusion and decreases the rate of threading. In addition, the presence of unsaturation in the alkyl substituent (allyl vs propyl and 4-butenyl vs butyl) results in an increase in the threading rate constant.

  DOI：

  10.1021/jo9808775

文献信息

• Catalytic Use of Indium(0) for Carbon−Carbon Bond Transformations in Water: General Catalytic Allylations of Ketones with Allylboronates
  作者：Uwe Schneider、Masaharu Ueno、Shu̅ Kobayashi

  DOI：10.1021/ja804182j

  日期：2008.10.22

  We have discovered the unprecedented catalytic use of In(0) for catalytic C-C bond transformations. Remarkably, these general catalytic allylations of ketones proceeded smoothly in water as a sole solvent under mild conditions, and water proved to be essential for these reactions. Both the displayed substrate scope and the functional group tolerance were excellent. Importantly, the In metal catalyst

  我们发现了 In(0) 在催化 CC 键转换中前所未有的催化用途。值得注意的是，这些酮的一般催化烯丙基化反应在温和条件下在作为唯一溶剂的水中顺利进行，并且水被证明是这些反应必不可少的。显示的底物范围和官能团耐受性都非常好。重要的是，In 金属催化剂可以很容易地回收和重复使用，而不会损失催化活性。此外，当使用 α 取代的烯丙基硼酸酯时，观察到不寻常的结构选择性，仅提供正式的 α 加合物。此外，得到的叔均烯丙基醇具有极高的非对映选择性。
• Carbon monoxide enabling synergistic carbonylation and (hetero)aryl migration
  作者：Yuanrui Wang、Hefei Yang、Yan Zheng、Mingxia Hu、Jintao Zhu、Zhi-Peng Bao、Yanying Zhao、Xiao-Feng Wu

  DOI：10.1038/s41929-024-01204-6

  日期：——

  catalytic systems to activate CO and then quench the generated acyl intermediate with nucleophiles to complete the carbonylative transformations. Here, non-classically, we unveil a visible-light-induced, carbonylation-triggered radical relay rearrangement reaction, in which the CO insertion step is a key element for functional group migration. The selective insertion of a carbonyl group into the newly generated

  一氧化碳 (CO)（一种多功能 C1 原料）的活化和转化继续引起广泛关注。传统上，研究人员专注于开发催化系统来活化CO，然后用亲核试剂猝灭生成的酰基中间体以完成羰基化转化。在这里，我们非经典地揭示了可见光诱导、羰基化触发的自由基中继重排反应，其中CO插入步骤是官能团迁移的关键要素。羰基选择性插入新生成的碳自由基中，为（杂）芳基迁移提供了桥梁，基团迁移的正反馈也使碳自由基能够更有效地捕获CO。在温和条件下成功合成了一系列含有氟烷基和杂环的1,4-二羰基化合物，并将产物转化为有价值的杂芳联芳化合物，表明了该平台的合成潜力。
• Catalytic Activation of Pinacolyl Allylboronate with Indium(I): Development of a General Catalytic Allylboration of Ketones
  作者：Uwe Schneider、Shū Kobayashi

  DOI：10.1002/anie.200700899

  日期：2007.8.3