4-(1-octynyl)pyridine | 144493-17-4

• 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-(1-octynyl)pyridine
• 英文别名: 4-oct-1-ynylpyridine
• CAS: 144493-17-4
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: MNMZESDGQYUNEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  295.5±13.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  苯丙醛 、 4-(1-octynyl)pyridine 生成 (E)-4-(1-Heptylidene-2-hydroxy-4-phenylbutyl)pyridine 、 (E)-4-(2-Hexyl-3-hydroxy-5-phenyl-1-pentenyl)pyridine
  参考文献：
  名称：

  Regioselectivity in the reaction of tantalum-unsymmetrical acetylene complexes with carbonyl compounds. Stereoselective preparation of 1-alkenyl sulfides, .alpha.,.beta.-unsaturated esters, and amides

  摘要：

  Tantalum-alkyne complexes, derived by treatment of alkynes with low-valent tantalum (TaCl5 and zinc), react in situ with carbonyl compounds to give (E)-allylic alcohols stereoselectively. When unsymmetrical acetylenes are employed in the reaction, two regioisomeric allylic alcohols are produced. The regioselectivity of the reaction depends on the steric and electronic effects of the substituents on the acetylenes. For example, treatment of tantalum-alkyne complexes derived from methyl alkynyl sulfides with carbonyl compounds yields (E)-3-hydroxy-1-propenyl methyl sulfides in a regioselective manner. Tantalum-alkyne complexes derived from acetylenic esters react with carbonyl compounds regioselectively at the alpha-position of the esters to give Z-isomers of trisubstituted alpha,beta-unsaturated esters. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds predominantly at the beta-position of the amides. The regioselectivity of the reaction between acetylenic amides and aldehydes, however, cannot be explained solely in terms of the steric and electronic effects of the substituents. Strong coordination of the amide group to the tantalum center could also be responsible for the observed selectivity, which is opposite to that observed with tantalum-acetylenic ester complexes.

  DOI：

  10.1021/jo00051a023
• 作为产物：
  描述：

  4-氯吡啶 、 1-辛炔 在 sodium tetrachloropalladate(II) 、 N,N'-bis(2,6-diisopropyl-4-sulfonatophenyl)imidazolium chloride 、 potassium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 12.0h， 生成 4-(1-octynyl)pyridine
  参考文献：
  名称：

  钯催化的Sonogashira和Suzuki-Miyaura偶联在水溶液中的磺化N-杂环卡宾

  摘要：

  所述的反应N，N' -diarylimidazolium和N，N'与在相应的二磺化的形成氯磺酸结果-diarylimidazolinium盐ñ -杂环卡宾（NHC）在合理的产率（46-77％）的前体。水溶性钯催化剂络合物，在原位从相应磺化咪唑啉盐获得，四氯钯钠（Na 2的PdCl 4）和水中的氢氧化钾（KOH）已成功用于异丙醇/水混合物中的无铜Sonogashira偶联反应中，催化剂用量为0.2 mol％。预先形成的（二磺化NHC）PdCl（肉桂基）络合物以0.1 mol％的催化剂负载量用于Suzuki-Miyaura水溶液中。此处报道的偶联方案对于N和S杂环芳基溴化物和氯化物与芳基和烷基乙炔的Sonogashira反应非常有用。

  DOI：

  10.1002/adsc.200900886

文献信息

• Process for preparing alkynyl-substituted aromatic and heterocyclic compounds
  申请人：Miller A. Joseph

  公开号：US20050137402A1

  公开（公告）日：2005-06-23

  Mono- and disubstituted aryl or heterocyclic acetylenes are produced by a process comprising reacting an aryl nitrile with an alkynylzinc compound, a bis-alkynylzinc compound, or an alkynylmagnesium compound, in the presence of a nickel/phosphine catalyst.

  通过在镍/膦催化剂存在下，将芳香族或杂环乙炔基腈与炔基锌化合物、双炔基锌化合物或炔基镁化合物反应，可以制备单取代和双取代的芳香族或杂环乙炔基化合物。
• Alkynylation of benzonitriles via nickel catalyzed C–C bond activation
  作者：Jonathan M. Penney、Joseph A. Miller

  DOI：10.1016/j.tetlet.2004.02.163

  日期：2004.6

  The scope of synthetically useful nickel catalyzed cross coupling reactions of benzonitriles has now been expanded to allow alkynylation. Thus, the cross coupling of benzonitriles with alkynylzinc reagents occurs readily in the presence of Ni/PMe3 based catalysts to afford the respective aryl alkynes in high yields. (C) 2004 Elsevier Ltd. All rights reserved.
• US7105707B2
  申请人：——

  公开号：US7105707B2

  公开（公告）日：2006-09-12
• Sulfonated N-Heterocyclic Carbenes for Pd-Catalyzed Sonogashira and Suzuki-Miyaura Coupling in Aqueous Solvents
  作者：Sutapa Roy、Herbert Plenio

  DOI：10.1002/adsc.200900886

  日期：——

  of the respective disulfonated N‐heterocyclic carbene (NHC) precursors in reasonable yields (46–77%). Water‐soluble palladium catalyst complexes, in situ obtained from the respective sulfonated imidazolinium salt, sodium tetrachloropalladate (Na2PdCl4) and potassium hydroxide (KOH) in water, were successfully applied in the copper‐free Sonogashira coupling reaction in isopropyl alcohol/water mixtures

  所述的反应N，N' -diarylimidazolium和N，N'与在相应的二磺化的形成氯磺酸结果-diarylimidazolinium盐ñ -杂环卡宾（NHC）在合理的产率（46-77％）的前体。水溶性钯催化剂络合物，在原位从相应磺化咪唑啉盐获得，四氯钯钠（Na 2的PdCl 4）和水中的氢氧化钾（KOH）已成功用于异丙醇/水混合物中的无铜Sonogashira偶联反应中，催化剂用量为0.2 mol％。预先形成的（二磺化NHC）PdCl（肉桂基）络合物以0.1 mol％的催化剂负载量用于Suzuki-Miyaura水溶液中。此处报道的偶联方案对于N和S杂环芳基溴化物和氯化物与芳基和烷基乙炔的Sonogashira反应非常有用。
• Regioselectivity in the reaction of tantalum-unsymmetrical acetylene complexes with carbonyl compounds. Stereoselective preparation of 1-alkenyl sulfides, .alpha.,.beta.-unsaturated esters, and amides
  作者：Yasutaka Kataoka、Jiro Miyai、Makoto Tezuka、Kazuhiko Takai、Kiitiro Utimoto

  DOI：10.1021/jo00051a023

  日期：1992.12

  Tantalum-alkyne complexes, derived by treatment of alkynes with low-valent tantalum (TaCl5 and zinc), react in situ with carbonyl compounds to give (E)-allylic alcohols stereoselectively. When unsymmetrical acetylenes are employed in the reaction, two regioisomeric allylic alcohols are produced. The regioselectivity of the reaction depends on the steric and electronic effects of the substituents on the acetylenes. For example, treatment of tantalum-alkyne complexes derived from methyl alkynyl sulfides with carbonyl compounds yields (E)-3-hydroxy-1-propenyl methyl sulfides in a regioselective manner. Tantalum-alkyne complexes derived from acetylenic esters react with carbonyl compounds regioselectively at the alpha-position of the esters to give Z-isomers of trisubstituted alpha,beta-unsaturated esters. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds predominantly at the beta-position of the amides. The regioselectivity of the reaction between acetylenic amides and aldehydes, however, cannot be explained solely in terms of the steric and electronic effects of the substituents. Strong coordination of the amide group to the tantalum center could also be responsible for the observed selectivity, which is opposite to that observed with tantalum-acetylenic ester complexes.