3-n-butyloxypyridine | 63361-61-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-n-butyloxypyridine
• 英文别名: 3-n-butoxypyridine；3-butoxypyridine；3-butoxy-pyridine；3-Butoxy-pyridin；3-Butoxypyridin
• CAS: 63361-61-5
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: SEFRRCOWPOLZOE-UHFFFAOYSA-N

物化性质

• 沸点：
  107-108 °C(Press: 13 Torr)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,4:3,5-di-O-benzylidenepentitol-1-yl)pyridine 、 3-n-butyloxypyridine 生成 (S)-[(4S,4aR,8aR)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]-(3-butoxypyridin-2-yl)methanol
  参考文献：
  名称：

  VRIJENS, I.;BELMANS, M.;ESMANS, E. L.;DOMMISSE, R.;LEPOIVRE, J. A.;ALDERW+, BIO-ORG. HETEROCYSLES, 1986: SYNTH., MECH. AND BIOACTIV.: PROC. 4TH FECHE+

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯吡啶 、 正丁醇 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 C₄₄H₄₇N₄P 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 3-n-butyloxypyridine
  参考文献：
  名称：

  钯催化 CO 交叉偶联脂肪族伯醇和仲醇的比较辅助配体调查

  摘要：

  研究了 RockPhos、Ad-BippyPhos、JosiPhos (CyPF-tBu) 和 Mor-DalPhos 在钯催化的 C-O 交叉偶联反应中的效用，该反应涉及类似条件下的脂肪醇和（杂）芳基卤化物，均在室温下进行并且在高温 (90 °C) 下。总的来说，基于 RockPhos 的催化剂体系被证明是优越的，尤其是在室温下，但基于其他配体的催化剂也被证明在一系列 C-O 交叉偶联中是有效的，在某些情况下提供比 RockPhos 更好的催化性能。根据室温反应的范围建立了新的反应性。还展示了涉及甲磺酸芳基酯的此类交叉偶联的原理证明示例。

  DOI：

  10.1002/ejoc.201600198

文献信息

• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• A General and Efficient Catalyst for Palladium-Catalyzed C−O Coupling Reactions of Aryl Halides with Primary Alcohols
  作者：Saravanan Gowrisankar、Alexey G. Sergeev、Pazhamalai Anbarasan、Anke Spannenberg、Helfried Neumann、Matthias Beller

  DOI：10.1021/ja103248d

  日期：2010.8.25

  An efficient procedure for palladium-catalyzed coupling reactions of (hetero)aryl bromides and chlorides with primary aliphatic alcohols has been developed. Key to the success is the synthesis and exploitation of the novel bulky di-1-adamantyl-substituted bipyrazolylphosphine ligand L6. Reaction of aryl halides including activated, nonactivated, and (hetero)aryl bromides as well as aryl chlorides with

  已开发出钯催化的（杂）芳基溴化物和氯化物与脂肪伯醇偶联反应的有效方法。成功的关键是合成和开发了新型庞大的二-1-金刚烷基取代的双吡唑基膦配体 L6。芳基卤化物，包括活化的、非活化的和（杂）芳基溴化物以及芳基氯化物与伯醇反应，以高产率得到相应的烷基芳基醚。值得注意的是，伯醇在仲醇和叔醇存在下的官能化具有出色的区域选择性。
• Copper-Catalyzed Coupling of Aryl Iodides with Aliphatic Alcohols
  作者：Martina Wolter、Gero Nordmann、Gabriel E. Job、Stephen L. Buchwald

  DOI：10.1021/ol025548k

  日期：2002.3.1

  and mild method for the coupling of aryl iodides and aliphatic alcohols that does not require the use of alkoxide bases is described. The reactions can be performed in neat alcohol. For more precious alcohols, the etherification was carried out in toluene as solvent using 2 equiv of alcohol. Additionally, the cross-coupling of an optically active benzylic alcohol with an unactivated aryl halide was demonstrated

  [反应：见正文]描述了一种简单而温和的偶联芳基碘化物和脂肪醇的方法，该方法不需要使用醇盐碱。反应可以在纯醇中进行。对于更珍贵的醇，醚化是在甲苯中作为溶剂，使用2当量的醇进行的。此外，光学活性的苯甲醇与未活化的芳基卤化物的交叉偶联被证明完全保留了构型。
• A Single Phosphine Ligand Allows Palladium-Catalyzed Intermolecular CO Bond Formation with Secondary and Primary Alcohols
  作者：Xiaoxing Wu、Brett P. Fors、Stephen L. Buchwald

  DOI：10.1002/anie.201104361

  日期：2011.10.10

  Forging a bond: An efficient, general palladium catalyst for CO bond‐forming reactions of secondary and primary alcohols with a range of aryl halides has been developed using the ligand 1. Heteroaryl halides, and for the first time, electron‐rich aryl halides can be coupled with secondary alcohols. A diverse set of substrate combinations are possible with just a single ligand, thus obviating the need

  形成键：使用配体1开发了一种高效、通用的钯催化剂，用于仲醇和伯醇与一系列芳基卤化物的C  O 键形成反应。杂芳基卤化物和富电子芳基卤化物首次可以与仲醇偶联。只需一个配体即可实现多种底物组合，因此无需调查多个配体。
• MCM-41-immobilized 1,10-phenanthroline–copper(<scp>i</scp>) complex: a highly efficient and recyclable catalyst for the coupling of aryl iodides with aliphatic alcohols
  作者：Yang Lin、Mingzhong Cai、Zhiqiang Fang、Hong Zhao

  DOI：10.1039/c6ra19825b

  日期：——

  A heterogeneous C–O coupling reaction between aryl iodides and aliphatic alcohols was achieved in neat alcohol or toluene at 110 °C in the presence of 10 mol% of the MCM-41-immobilized 1,10-phenanthroline–copper(I) complex [MCM-41-1,10-phen–CuI] with Cs2CO3 as a base, yielding a variety of aryl alkyl ethers in good to excellent yields. The new heterogeneous copper catalyst can easily be prepared by

  在存在10 mol％的MCM-41固定的1,10-菲咯啉-铜（I）络合物的存在下，在110°C的纯醇或甲苯中，芳基碘化物和脂肪醇之间的异质C-O偶联反应得以实现[以Cs 2 CO 3为碱的MCM-41-1,10-phen-CuI] ，可产生各种芳基烷基醚，收率好至极佳。新的多相铜催化剂可以很容易地通过简单的方法由市售和廉价的试剂制备，并通过过滤反应溶液进行回收并循环至少8次而不会显着降低活性。