4-chloro-2-((4-chlorophenyl)ethynyl)phenol | 1393097-99-8

• 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-((4-chlorophenyl)ethynyl)phenol
• CAS: 1393097-99-8
• 化学式: C₁₄H₈Cl₂O
• 分子量: 263.123
• InChiKey: SYXZAMHAASAWSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  0.0
• 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-((4-chlorophenyl)ethynyl)phenol 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.0h， 以44%的产率得到5-chloro-2-(4-chlorophenyl)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-((4-chlorophenyl)ethynyl)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

• Generation of cyclopenta[c]chromenes via a palladium-catalyzed reaction of 2-alkynylphenol with 2-alkynylvinyl bromide
  作者：Huanhuan Wang、Yong Luo、Biao Zhu、Jie Wu

  DOI：10.1039/c2cc32077k

  日期：——

  A palladium-catalyzed tandem reaction of 2-alkynylphenol with 2-alkynylvinyl bromide gives rise to cyclopenta[c]chromenes in good yields. Three bonds are formed during the process and a double insertion of triple bonds is believed to be the key step.

  在钯催化下，2-炔基苯酚与 2-炔基溴化乙烯发生串联反应，以良好的收率生成环戊并[c]色烯。在此过程中形成了三个键，三键的双插入被认为是关键步骤。