2-(1-(pyridin-3-yl)vinyl)phenol | 1275593-38-8

• 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-(1-(pyridin-3-yl)vinyl)phenol
• 英文别名: 2-(1-Pyridin-3-ylethenyl)phenol；2-(1-pyridin-3-ylethenyl)phenol
• CAS: 1275593-38-8
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: ZCPFJGMCNOYHET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-(pyridin-3-yl)vinyl)phenol 在 Rh(COD)[(R,S)-DuanPhos]BF₄ 、 氢气 、 三乙胺 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 4.0h， 以91%的产率得到(S)-2-(1-(pyridin-3-yl)ethyl)phenol
  参考文献：
  名称：

  Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups

  摘要：

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.

  DOI：

  10.1021/ol200422p
• 作为产物：
  描述：

  3-乙酰基吡啶 在 正丁基锂 、 对甲苯磺酸 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 3.5h， 生成 2-(1-(pyridin-3-yl)vinyl)phenol
  参考文献：
  名称：

  Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups

  摘要：

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.

  DOI：

  10.1021/ol200422p

文献信息

• Sequential One-Pot Synthesis of 3-Arylbenzofurans from <i>N</i>-Tosylhydrazones and Bromophenol Derivatives
  作者：Diana Lamaa、Camille Hauguel、Hsin-Ping Lin、Estelle Messe、Vincent Gandon、Mouad Alami、Abdallah Hamze

  DOI：10.1021/acs.joc.0c01835

  日期：2020.11.6

  A divergent and efficient one-pot sequence allowing direct access to 3-arylbenzofuran derivatives has been developed. The process, involving N-tosylhydrazones and bromophenols, proceeds via a palladium-catalyzed Barluenga–Valdés cross-coupling, followed by an aerobic, copper-catalyzed, radical cyclization to form Csp2–Csp2 and O–Csp2 bonds. 3-Arylated benzofurans bearing various substituents were obtained

  已经开发出允许直接获得3-芳基苯并呋喃衍生物的发散且有效的一锅序列。该过程涉及N-甲苯磺酰hydr和溴酚，通过钯催化的Barluenga-Valdés交叉偶联进行，然后进行需氧，铜催化的自由基环化，形成Csp 2 -Csp 2和O-Csp 2键。获得具有各种取代基的3-丙烯酸化的苯并呋喃，具有良好至优异的产率（高达90％）。机理研究强烈支持环化步骤的根本过程。
• Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups
  作者：Xiang Wang、Anil Guram、Seb Caille、Jack Hu、J P. Preston、Michael Ronk、Shawn Walker

  DOI：10.1021/ol200422p

  日期：2011.4.1

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.