2-(3-methylbenzyloxy)pyridine | 40775-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-methylbenzyloxy)pyridine
• 英文别名: 2-[(3-methylphenyl)methoxy]pyridine；2-[(3-Methylphenyl)methoxy]pyridine
• CAS: 40775-70-0
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: MULFFQZFPRDDAT-UHFFFAOYSA-N

物化性质

• 沸点：
  306.8±22.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-(3-methylbenzyloxy)pyridine 在 lithium iodide 作用下， 反应 8.0h， 以96%的产率得到N-(3-甲基苄基)-2-吡啶酮
  参考文献：
  名称：

  通过O-向N-烷基的迁移合成取代的N-苄基吡啶酮。

  摘要：

  已经开发了一种新的由LiI促进的O-到N-烷基迁移，可将O-烷基化的2-羟基吡啶，喹啉和嘧啶以良好至极好的收率（57-99％）转化为相应的N-烷基化杂环。该方法用作制备N-苄基吡啶酮，喹诺酮和嘧啶酮的有效方法。

  DOI：

  10.1021/jo800866w
• 作为产物：
  描述：

  2-氯吡啶 、 3-甲基苄醇 在 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以91%的产率得到2-(3-methylbenzyloxy)pyridine
  参考文献：
  名称：

  通过O-向N-烷基的迁移合成取代的N-苄基吡啶酮。

  摘要：

  已经开发了一种新的由LiI促进的O-到N-烷基迁移，可将O-烷基化的2-羟基吡啶，喹啉和嘧啶以良好至极好的收率（57-99％）转化为相应的N-烷基化杂环。该方法用作制备N-苄基吡啶酮，喹诺酮和嘧啶酮的有效方法。

  DOI：

  10.1021/jo800866w

文献信息

• Preparation of <i>N</i>-Alkyl 2-Pyridones via a Lithium Iodide Promoted <i>O</i>- to <i>N</i>-Alkyl Migration: Scope and Mechanism
  作者：Sarah Z. Tasker、Michael A. Bosscher、Christina A. Shandro、Erica L. Lanni、Keun Ah Ryu、Gregory S. Snapper、Jarrad M. Utter、Bruce A. Ellsworth、Carolyn E. Anderson

  DOI：10.1021/jo3015424

  日期：2012.9.21

  An efficient and inexpensive LiI-promoted O- to N-alkyl migration of 2-benzyloxy-, 2-allyloxy-, and 2-propargyloxypyridines and heterocycles is reported. The reaction produces the corresponding N-alkyl 2-pyridones and analogues under green, solvent-free conditions in good to excellent yields (30 examples, 20–97% yield). This method has been shown to be intermolecular and requires heat and lithium cation

  报道了一种有效且廉价的LiI促进的2-苄氧基-，2-烯丙氧基-和2-炔丙基氧基吡啶和杂环的O-向N-烷基的迁移。在绿色，无溶剂的条件下，该反应可产生相应的N-烷基2-吡啶酮和类似物，收率好至极佳（30例，收率20-97％）。已经证明该方法是分子间的，并且需要热量和锂阳离子才能发生。
• Homocoupling of benzyl pyridyl ethers <i>via</i> visible light-mediated deoxygenation
  作者：Jingtian Chen、Fan Wang、Xiang Li、Lei Wang、Wei Yu、Keju Sun、Jingyue Yang

  DOI：10.1039/d3cc03002d

  日期：——

  The photocatalytic coupling of ethers is uncommon because of the challenges in breaking C–O bonds and low selectivity. Herein, we report a visible light-mediated deoxygenation homocoupling of benzyl pyridyl ethers via their pyridium salts. This approach enables C(sp3)–O bond homolysis under mild conditions. Mechanistic experiments support the radical nature of the reaction. This method is highly compatible

  由于打破 C-O 键和低选择性的挑战，醚的光催化偶联并不常见。在此，我们报道了苄基吡啶基醚通过其吡啶盐进行可见光介导的脱氧自偶联。这种方法能够在温和条件下实现 C(sp 3 )–O 键均裂。机理实验支持该反应的激进性质。该方法与吸电子基团高度相容，在药物前体合成方面具有潜在的应用前景。
• Sequential <i>ortho</i>-C–H and <i>ipso</i>-C–O Functionalization Using a Bifunctional Directing Group
  作者：Jingjing Chen、Jiancong Xu、Yu Zhou、Shuguang Xie、Feng Gao、Xiufang Xu、Xiaohua Xu、Zhong Jin

  DOI：10.1021/acs.orglett.9b02910

  日期：2019.10.4

  Design of C-H activation directing groups that can serve as electrophiles for subsequent cross-coupling significantly improves the step economy of synthetic applications of directed C-H functionalization. Through using a well-defined bifunctional template, palladium-catalyzed ortho-C-H alkenylation and arylation of benzylic alcohols was achieved via an end-on nitrile-embedded 12-membered macrocyclic transition state. Thereafter, the directing template is used as a handle for palladium-catalyzed ipso-C-O cross-coupling to provide functionalized diarylmethanes.
• BICYCLIC HETEROARYL AMINE COMPOUNDS AS PI3K INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP3209664B1

  公开（公告）日：2020-06-03
• BICYCLIC HETEROARYL AMINE COMPOUNDS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20170355707A1

  公开（公告）日：2017-12-14

  Disclosed are compounds of Formula (I) or a salt thereof; wherein: X is N or CH; Q 1 is: (i) Cl, Br, I, —CN, —CH 3 , or —CF 3 ; (ii) a 5-membered heteroaryl selected from pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, oxadiazolyl, and thiadiazolyl; (iii) a 6?membered heteroaryl selected from pyridinyl, pyridazinyl, and pyrimidinyl; or (iv) a bicyclic heteroaryl selected from indolyl, pyrrolopyridinyl, pyrazolopyridinyl and benzo[d]oxazolyl; wherein each of said 5-membered, 6-membered, and bicyclic heteroaryl is substituted with zero to 1 R a and zero to 1 R b ; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R a , and R b are defined herein. Also disclosed are methods of using such compounds as modulators of PI3K, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing inflammatory and autoimmune diseases.