3-(pyrid-4-yl)pentan-3-ol | 19731-60-3

• 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: 3-(pyrid-4-yl)pentan-3-ol
• 英文别名: 4-(α,α-diethylmethanol)pyridine；(ethyl-1 propanol-1)-4 pyridine；3--pentanol-(3)；3-pyridin-4-yl-pentan-3-ol；3-Pyridin-4-ylpentan-3-ol
• CAS: 19731-60-3
• 化学式: C₁₀H₁₅NO
• mdl: MFCD18803107
• 分子量: 165.235
• InChiKey: PUDAFGXRSMFBKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  284.3±15.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-(pyrid-4-yl)pentan-3-ol 、 1,12-二溴十二烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以75%的产率得到1,12-bis(4-(α,α-diethylmethanol)pyridinium)dodecane dibromide
  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-氯吡啶 、 苄叉丙酮 在 萘 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到3-(pyrid-4-yl)pentan-3-ol
  参考文献：
  名称：

  萘催化氯化硝化芳香杂环的锂化反应及与亲电试剂的反应

  摘要：

  萘催化各种chloroazines的还原性锂化（1，7，10，13以不同的亲电子的产率的情况下），在水解后，预期的官能化杂环与一个（2，8），两个（11，14A - d）和三个氮环（14e，f）中的原子。这种方法使我们能够在烷氧基钛存在下，通过与格氏试剂反应，将2-吡啶基锂与苄腈反应衍生的亚胺锂原位捕获。2,4-二甲氧基嘧啶（14a，c，d）在酸性条件下脱甲基，得到相应的尿嘧啶衍生物16。

  DOI：

  10.1016/s0040-4020(00)00318-5

文献信息

• Reaction de la bromo-3 pyridine avec le diisopropylamidure de lithium. Mecanismes de metallation et de migration d'halogene. Regioselectivite de l'addition polaire sur la pyridyne-3,4
  作者：M. Mallet、G. Quénguiner

  DOI：10.1016/0040-4020(82)80190-7

  日期：1982.1

  3-bromo pyridine behaviour towards lithium diisopropyl amide (LDA) in THF is studied. A careful study of the experimental conditions point to a metallation reaction in position 4 and a “halogen dance” mechanism with isomerisation into a 4-bromo pyridine. Conversion into diisopropylamino compounds occurs simultaneously with a 3 oriented elimination-addition (EA) reaction from transient isomeric lithio-derivatives

  研究了3-溴吡啶在THF中对二异丙基氨基锂（LDA）的行为。对实验条件的仔细研究指出了位置4的金属化反应和异构化成4-溴吡啶的“卤素舞”机理。转化为二异丙基氨基化合物的过程与瞬时异构体硫代衍生物的3向消除-加成（EA）反应和原位形成的4-溴吡啶的竞争加成-消除（AE）机理同时发生。
• MALLET, M.;QUEGUINER, G., TETRAHEDRON, 1982, 38, N 20, 3035-3042
  作者：MALLET, M.、QUEGUINER, G.

  DOI：——

  日期：——
• Naphthalene-catalysed Lithiation of Chlorinated Nitrogenated Aromatic Heterocycles and Reaction with Electrophiles
  作者：Inmaculada Gómez、Emma Alonso、Diego J Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(00)00318-5

  日期：2000.6

  Naphthalene catalysed reductive lithiation of various chloroazines (1, 7, 10, 13) in the presence of different electrophiles yields, after hydrolysis, the expected functionalised heterocycles with one (2, 8), two (11, 14a–d) and three nitrogen atoms in the ring (14e,f). This methodology allowed us to trap in situ the lithium imine derived from the reaction of 2-pyridyllithium with benzonitrile, by

  萘催化各种chloroazines的还原性锂化（1，7，10，13以不同的亲电子的产率的情况下），在水解后，预期的官能化杂环与一个（2，8），两个（11，14A - d）和三个氮环（14e，f）中的原子。这种方法使我们能够在烷氧基钛存在下，通过与格氏试剂反应，将2-吡啶基锂与苄腈反应衍生的亚胺锂原位捕获。2,4-二甲氧基嘧啶（14a，c，d）在酸性条件下脱甲基，得到相应的尿嘧啶衍生物16。
• 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
  作者：A. Catherine Smith、Donal H. Macartney

  DOI：10.1021/jo9808775

  日期：1998.12.1

  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.