3-hydroxy-2-(3-methoxyphenyl)cyclohex-2-en-1-one | 163128-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-hydroxy-2-(3-methoxyphenyl)cyclohex-2-en-1-one
• 英文别名: 3-Hydroxy-2-(3-methoxyphenyl)cyclohex-2-en-1-one
• CAS: 163128-82-3
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: KISWSVBEKAQLPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸烯丙酯 、 3-hydroxy-2-(3-methoxyphenyl)cyclohex-2-en-1-one 在 copper diacetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以40%的产率得到6-ethenyl-9-methoxy-1H,2H,3H,4H,6H-benzo[c]chromen-1-one
  参考文献：
  名称：

  Palladium-catalyzed double C–H functionalization of 2-aryl-1,3-dicarbonyl compounds: a facile access to alkenylated benzopyrans

  摘要：

  The present study reports the development of a palladium-catalyzed oxidative annulation/nucleophilic substitution sequence affording a library of alkenylated benzopyrans using 2-aryl-1,3-dicarbonyl compounds and allylic acetate. The process is compatible to a wide range of substrates with good functional group tolerance producing the desired heterocycles in moderate to good yields. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.04.089
• 作为产物：
  描述：

  3-碘苯甲醚 、 1,3-环己二酮 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以73%的产率得到3-hydroxy-2-(3-methoxyphenyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  的C功能化？H和C ？H键：烯醇基直接催化钌催化的炔烃与2-芳基-1,3-二羰基化合物的环氧化合成螺茚

  摘要：

  Ru（de）唤醒：描述了通过钌催化的炔烃与2-芳基环状1,3-二羰基底物的合成碳环。通过CH和CH键的功能化，以及全碳四元中心的形成，该反应以高收率和高区域选择性提供了多种螺环茚。

  DOI：

  10.1002/anie.201207170

文献信息

• Redox-Neutral Ruthenium(II)-Catalyzed Enol-Directed Arene C–H Alkylation with Maleimides
  作者：Sudeshna Mondal、Ratnadeep Bera、Deepan Chowdhury、Suman Dana、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.2c03858

  日期：2023.1.13

  developed under redox-neutral ruthenium(II) catalysis, offering a wide variety of valuable 3-aryl succinimides including amino acid embedded frameworks in good to excellent yields. The products were also aromatized to produce synthetically useful resorcinol-based biaryls. Mechanistic studies support an organometallic pathway with a reversible C–H metalation step for this reaction.

  在氧化还原中性钌 (II) 催化下开发了一种烯醇辅助的区域选择性芳烃 C-H 与马来酰亚胺的烷基化反应，提供了多种有价值的 3-芳基琥珀酰亚胺，包括氨基酸嵌入框架，收率良好至极佳。产物也被芳构化以产生合成有用的基于间苯二酚的联芳基化合物。机理研究支持有机金属途径与该反应的可逆 C-H 金属化步骤。
• Synthesis of Benzopyrans by Pd(II)- or Ru(II)-Catalyzed C–H Alkenylation of 2-Aryl-3-hydroxy-2-cyclohexenones
  作者：Suresh Reddy Chidipudi、Martin D. Wieczysty、Imtiaz Khan、Hon Wai Lam

  DOI：10.1021/ol3033835

  日期：2013.2.1

  2-Aryl-3-hydroxy-2-cyclohexenones are shown to be competent substrates for palladium- and ruthenium-catalyzed C-H alkenylation reactions with terminal alkenes, providing, in most cases, benzopyrans.
• Functionalization of C sp 3H and C sp 2H Bonds: Synthesis of Spiroindenes by Enolate-Directed Ruthenium-Catalyzed Oxidative Annulation of Alkynes with 2-Aryl-1,3-dicarbonyl Compounds
  作者：Suresh Reddy Chidipudi、Imtiaz Khan、Hon Wai Lam

  DOI：10.1002/anie.201207170

  日期：2012.11.26

  Ru(de) awakening: The synthesis of carbocycles by the ruthenium‐catalyzed oxidative annulation of alkynes with 2‐aryl cyclic 1,3‐dicarbonyl substrates is described. Proceeding by the functionalization of CH and CH bonds, and the formation of an all‐carbon quaternary center, the reaction provides a diverse range of spiroindenes in good yields with high levels of regioselectivity.

  Ru（de）唤醒：描述了通过钌催化的炔烃与2-芳基环状1,3-二羰基底物的合成碳环。通过CH和CH键的功能化，以及全碳四元中心的形成，该反应以高收率和高区域选择性提供了多种螺环茚。
• Palladium-catalyzed double C–H functionalization of 2-aryl-1,3-dicarbonyl compounds: a facile access to alkenylated benzopyrans
  作者：Subrahmanyam Choppakatla、Aravind Kumar Dachepally、Hari Babu Bollikolla

  DOI：10.1016/j.tetlet.2016.04.089

  日期：2016.6

  The present study reports the development of a palladium-catalyzed oxidative annulation/nucleophilic substitution sequence affording a library of alkenylated benzopyrans using 2-aryl-1,3-dicarbonyl compounds and allylic acetate. The process is compatible to a wide range of substrates with good functional group tolerance producing the desired heterocycles in moderate to good yields. (C) 2016 Elsevier Ltd. All rights reserved.