4-((4-methoxyphenyl)(pyridin-2-yl)methyl)morpholine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-((4-methoxyphenyl)(pyridin-2-yl)methyl)morpholine
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: RREGLZRLVQDKHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  34.59
• 氢给体数：
  0.0
• 氢受体数：
  4.0

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 4-((4-methoxyphenyl)(pyridin-2-yl)methyl)morpholine
  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

• An efficient HCl promoted Petasis reaction of 2-pyridinecarbaldehydes, amines and 1,2-oxborol-2(5H)-ols
  作者：Tao Ding、Yazhen Duan、Hui Li、Baoguo Zhao、Jun Yang

  DOI：10.1016/j.tetlet.2018.04.013

  日期：2018.6

  A Petasis reaction of 2-pyridinecarbaldehydes with various amines and 4-substituted 1,2-oxaborol-2(5H)-ols was developed. In the presence of HCl, the reaction proceeded smoothly under very mild conditions and the corresponding desired products were obtained in medium to excellent yields. This method allows the access a wide range of highly functionalized allylic alcohols, which might be useful compounds

  开发了2-吡啶甲醛与各种胺和4-取代的1,2-氧杂硼-2（5H）-醇的Petasis反应。在HCl的存在下，反应在非常温和的条件下顺利进行，并以中等至优异的产率获得了相应的所需产物。这种方法可以使用各种高度官能化的烯丙醇，这可能在药物和材料化学中是有用的化合物。
• Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr ₂ /NIXANTPHOS‐based Catalyst
  作者：Gui Gao、Yue Fu、Minyan Li、Bo Wang、Bing Zheng、Shicong Hou、Patrick J. Walsh

  DOI：10.1002/adsc.201700438

  日期：2017.8.17

  A nickel‐catalyzed coupling of azaarylmethylamines with aryl chlorides has been achieved. NIXANTPHOS together with low cost NiBr2 was successfully developed and optimized to exhibit high reactivity at 2.5 mol % loading. Under optimized reaction conditions, aryl(azaaryl)methylamine products were afforded in good to excellent yields (22 examples, up to 98% yield).

  已经实现了镍催化的氮杂芳基甲胺与芳基氯化物的偶联。NIXANTPHOS与低成本NiBr 2一起成功开发并优化，以在2.5 mol％的装载量下表现出高反应活性。在优化的反应条件下，芳基（氮杂芳基）甲胺产品的收率好至极佳（22个实例，最高收率98％）。
• 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.