2-(N,N-diethylaminobenzyl)pyridine | 123839-86-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(N,N-diethylaminobenzyl)pyridine
• 英文别名: N-ethyl-N-(phenyl(pyridin-2-yl)methyl)ethanamine；N-ethyl-N-[phenyl(pyridin-2-yl)methyl]ethanamine
• CAS: 123839-86-1
• 化学式: C₁₆H₂₀N₂
• 分子量: 240.348
• InChiKey: SGDDSJKOEYAQKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯甲基吡啶盐酸盐 在 palladium diacetate 、 potassium carbonate 、 sodium iodide 、 lithium hexamethyldisilazane 、 4,6-二(二苯基膦)吩嗪 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 24.0h， 生成 2-(N,N-diethylaminobenzyl)pyridine
  参考文献：
  名称：

  Palladium-Catalyzed Benzylic C–H Arylation of Azaarylmethylamines

  摘要：

  A direct C-H functionalization approach to produce aryl(azaaryl)methylamines from azaarylmethylamines without directing groups is described. Under conditions where the azaarylmethylamines' C-H is reversibly deprotonated, a Pd(OAc)(2)/NIXANTPHOS-based catalyst couples the resulting carbanions with various aryl halides to provide aryl-(azaaryl)methylamines This umpolung strategy directly provides tertiary amines without protecting or activating groups.

  DOI：

  10.1021/acs.orglett.5b02898

文献信息

• A Copper-Catalyzed Petasis Reaction for the Synthesis of Tertiary Amines and Amino Esters
  作者：Robin Frauenlob、Carlos García、Gary A. Bradshaw、Helen M. Burke、Enda Bergin

  DOI：10.1021/jo3003503

  日期：2012.5.4

  We have developed a copper-catalyzed process for the coupling of aldehydes, amines, and boronic acids. This allows greater reactivity with simple aryl boronic acids and allows coupling reactions to proceed that previously failed. Initial mechanistic studies support a process involving transmetalation from boron to copper.

  我们已经开发了一种铜催化的醛，胺和硼酸偶联方法。这使得与简单的芳基硼酸的反应性更高，并使偶联反应得以进行，而该反应以前是失败的。最初的力学研究支持涉及从硼到铜的过渡金属化的过程。
• Ivanov, A. P.; Levin, D. Z.; Mortikov, E. S., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 3.2, p. 566 - 570
  作者：Ivanov, A. P.、Levin, D. Z.、Mortikov, E. S.、Promonenkov, V. K.

  DOI：——

  日期：——
• IVANOV, A. P.;LEVIN, D. Z.;MORTIKOV, E. S.;PROMONENKOV, V. K., ZH. ORGAN. XIMII, 25,(1989) N, S. 629-633
  作者：IVANOV, A. P.、LEVIN, D. Z.、MORTIKOV, E. S.、PROMONENKOV, V. K.

  DOI：——

  日期：——
• IVANOV, A. P.;LEVIN, D. Z.;PROMONENKOV, V. K.;MORTIKOV, E. S., XIMIYA I TEXNOL. PIRIDINSODERZH. PESTITSIDOV, B. M.,(B. G.) S. 67
  作者：IVANOV, A. P.、LEVIN, D. Z.、PROMONENKOV, V. K.、MORTIKOV, E. S.

  DOI：——

  日期：——
• Palladium-Catalyzed Benzylic C–H Arylation of Azaarylmethylamines
  作者：Byeong-Seon Kim、Jacqueline Jiménez、Feng Gao、Patrick J. Walsh

  DOI：10.1021/acs.orglett.5b02898

  日期：2015.12.4

  A direct C-H functionalization approach to produce aryl(azaaryl)methylamines from azaarylmethylamines without directing groups is described. Under conditions where the azaarylmethylamines' C-H is reversibly deprotonated, a Pd(OAc)(2)/NIXANTPHOS-based catalyst couples the resulting carbanions with various aryl halides to provide aryl-(azaaryl)methylamines This umpolung strategy directly provides tertiary amines without protecting or activating groups.