4-chloro-2-(p-tolylethynyl)phenol | 1338699-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-chloro-2-(p-tolylethynyl)phenol
• CAS: 1338699-37-8
• 化学式: C₁₅H₁₁ClO
• 分子量: 242.705
• InChiKey: AJDKYZVKWLWCMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(p-tolylethynyl)phenol 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以70%的产率得到5-chloro-2-(4-methylphenyl)benzofuran
  参考文献：
  名称：

  Highly efficient heterogeneous synthesis of benzofurans under aqueous condition

  摘要：

  Highly efficient organic reactions in water are important for designing environmental-friendly and low cost synthetic processes. Herein, we demonstrate an intermediate-in-water strategy for the heterogeneous synthesis of benzofurans in aqueous media. The cyclization reaction of 2-(phenylethynyl)phenol to 2-phenylbenzofuran cannot proceed in pure water. However, this reaction can be efficiently promoted by the formation of sparingly soluble intermediate in the presence of alkaline. Quantitative conversion of a variety of substrates to benzofuran derivatives has been achieved in the absence of noble metal catalyst. Other remarkable features including easy-isolation and purification of product, along with wide range of functional group tolerance render the methodology promising in the realm of green-synthesis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.005
• 作为产物：
  描述：

  4-氯-2-碘苯酚 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-chloro-2-(p-tolylethynyl)phenol
  参考文献：
  名称：

  Highly efficient heterogeneous synthesis of benzofurans under aqueous condition

  摘要：

  Highly efficient organic reactions in water are important for designing environmental-friendly and low cost synthetic processes. Herein, we demonstrate an intermediate-in-water strategy for the heterogeneous synthesis of benzofurans in aqueous media. The cyclization reaction of 2-(phenylethynyl)phenol to 2-phenylbenzofuran cannot proceed in pure water. However, this reaction can be efficiently promoted by the formation of sparingly soluble intermediate in the presence of alkaline. Quantitative conversion of a variety of substrates to benzofuran derivatives has been achieved in the absence of noble metal catalyst. Other remarkable features including easy-isolation and purification of product, along with wide range of functional group tolerance render the methodology promising in the realm of green-synthesis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.005

文献信息

• A palladium-catalyzed tandem reaction of 2-(2-bromobenzylidene)cyclobutanone with 2-alkynylphenol
  作者：Xiaolin Pan、Yong Luo、Hong-Guang Xia、Jie Wu

  DOI：10.1039/c5cc07360j

  日期：——

  An efficient approach for the generation of benzo[b]naphtho[2,3-d]oxocin-6-ones through a palladium-catalyzed tandem reaction of 2-alkynylphenol with 2-(2-bromobenzylidene)cyclobutanone is described. This tandem process afforded the fused polycycles easily, with the formation of three bonds with high efficiency and excellent selectivity.

  通过钯催化的2-炔基苯酚与2-(2-溴苯基亚甲基)环丁酮的串联反应，描述了一种高效的制备苯并[b]萘并[2,3-d]氧喹啉-6-酮的方法。这种串联过程容易地形成融合多环化合物，高效地形成三个键，并具有优异的选择性。
• Access to 6H-naphtho[2,3-c]chromenes by a palladium-catalyzed reaction of 2-haloaryl allene with 2-alkynylphenol
  作者：Xiaolin Pan、Mo Chen、Liangqing Yao、Jie Wu

  DOI：10.1039/c4cc00374h

  日期：——

  A palladium-catalyzed reaction of 2-haloaryl allene with 2-alkynylphenol is described, leading to 6H-naphtho[2,3-c]chromenes in good to excellent yields. This transformation proceeds efficiently with excellent chemoselectivity and regioselectivity.

  描述了一种钯催化的反应，将2-卤代芳基炔丙烯与2-炔基苯酚反应，生成6H-萘[2,3-c]色烯，产率良好到优良。该转化反应高效进行，具有优异的化学选择性和区域选择性。
• A New Insight into Palladium-Catalyzed Reaction of 2-Alkynylphenol with Carbon Monoxide
  作者：Yong Luo、Jie Wu

  DOI：10.1021/ol202478u

  日期：2011.11.4

  A novel and efficient pathway for the generation of 3-(benzofuran-3-ylmethylene)benzofuran-2(3H)-ones via a palladium-catalyzed carbonylative reaction of 2-alkynylphenol with carbon monoxide is described. The reaction proceeds through a double insertion of triple bonds during the reaction process. The products are obtained in good yields with high selectivity. A one-pot synthesis starting from 2-iodophenol

  描述了通过钯催化的2-炔基苯酚与一氧化碳的羰基化反应生成3-（苯并呋喃-3-基亚甲基）苯并呋喃-2（3 H）-的新颖而有效的途径。反应在反应过程中通过三键的两次插入而进行。以高收率和高选择性获得产物。还提出了一种从2-碘苯酚和炔烃开始的一锅法合成法。
• Assembly of Indeno[1,2-<i>c</i>]chromenes<i>via</i>a Palladium-Catalyzed Reaction of 1-Bromo-2-(cyclopropylidenemethyl)benzene with 2-Alkynylphenol
  作者：Xiaolin Pan、Yong Luo、Yechun Ding、Xiaona Fan、Jie Wu

  DOI：10.1002/adsc.201300942

  日期：2014.3.24

  1‐Bromo‐2‐(cyclopropylidenemethyl)benzenes react with 2‐alkynylphenols under palladium catalysis, leading to indeno[1,2‐c]chromenes in moderate to good yields. The molecular complexity and diversity can be introduced efficiently from easily available starting materials.

  1-溴-2-（环亚丙基甲基）苯在钯催化下与2-炔基苯酚反应，生成中等产率至中等产率的茚并[1,2- c ]二甲基苯。分子的复杂性和多样性可以从容易获得的原料中有效地引入。