4-chloro-4'-methoxy-[1,1'-biphenyl]-2-ol | 959995-20-1

• 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: 4-chloro-4'-methoxy-[1,1'-biphenyl]-2-ol
• 英文别名: 5-chloro-2-(4-methoxyphenyl)phenol；5-Chloro-2-(4-methoxyphenyl)phenol
• CAS: 959995-20-1
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: KFVGWISXAHLFOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-4'-methoxy-[1,1'-biphenyl]-2-ol 、 一氧化碳 在 [RhCl2(p-cymene)]2 、 氧气 、 caesium carbonate 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 、 三甲基乙酸 作用下， 以 均三甲苯 为溶剂， 反应 24.0h， 以55%的产率得到3-chloro-8-methoxy-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Ruthenium-Catalyzed Carbonylative C–H Cyclization of 2-Arylphenols: A Novel Synthetic Route to 6H-Dibenzo[b,d]pyran-6-ones

  摘要：

  Catalytic carbonylative C-H cyclization of 2-arylphenols can be achieved in the presence of a ruthenium-based catalytic system. The process proceeds efficiently under balloon pressure of CO and produces variously substituted 6H-dibenzo[b,d]pyran-6-one compounds, typically in good to high yields. Functional groups such as the alkoxycarbonyl and acetyl groups as well as halogen atoms (F, Cl, and Br) are well tolerated during the reaction.

  DOI：

  10.1021/ol401734m
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 4-chloro-4'-methoxy-[1,1'-biphenyl]-2-ol
  参考文献：
  名称：

  Directed Ortho Borylation of Phenol Derivatives Catalyzed by a Silica-Supported Iridium Complex

  摘要：

  The directed ortho borylation of phenol derivatives protected with an N,N-diethylcarbamoyl group was efficiently catalyzed by an immobilized monophosphine-Ir system, which was prepared in situ from [Ir(OMe)(cod)](2) and a silica-supported, compact phosphine. The utility of the carbamoyloxy group as a leaving group for metal-catalyzed cross-coupling reactions was demonstrated by its utilization in the synthesis of a terphenyl derivative.

  DOI：

  10.1021/ol101493m

文献信息

• Synthesis of Substituted Monohalobenzenes via Ortho-Selective Cross-Coupling of Dihalobenzenes with Electron-Donating Ortho-Directing Groups
  作者：Kei Manabe、Shunpei Ishikawa

  DOI：10.1055/s-2008-1067270

  日期：2008.10

  Dihalobenzenes that possess directing groups such as OH, CH 2 OH, NH 2 , NHAc, or NHBoc were subjected to ortho-selective cross-coupling with Grignard reagents in the presence of palladium-based catalysts to give the corresponding substituted monohalobenzenes. For the dibromo- and dichlorophenols and anilines, hydroxylated terphenylphosphines 1 and 2 were found to be effective ligands for palladium

  在钯基催化剂存在下，将具有导向基团如 OH、CH 2 OH、NH 2 、NHAc 或 NHBoc 的二卤代苯与格氏试剂进行邻位选择性交叉偶联，得到相应的取代单卤代苯。对于二溴和二氯苯酚和苯胺，羟基化三联苯膦 1 和 2 被发现是钯的有效配体，而三环己基膦对于二氯苯甲醇、二氯苯胺和二氟苯来说是优选的。
• Highly Ortho-Selective Cross-Coupling of Dichlorobenzene Derivatives with Grignard Reagents
  作者：Shunpei Ishikawa、Kei Manabe

  DOI：10.1021/ol702646s

  日期：2007.12.1

  Highly ortho-selective cross-coupling of dichlorobenzene derivatives with Grignard reagents was realized using a combination of Pd-2(dba)(3) and PCy3. Use of hydroxylated terphenylphosphines further improved the reactions of dichlorophenol and dichloroaniline.
• Directed Ortho Borylation of Phenol Derivatives Catalyzed by a Silica-Supported Iridium Complex
  作者：Kenji Yamazaki、Soichiro Kawamorita、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/ol101493m

  日期：2010.9.17

  The directed ortho borylation of phenol derivatives protected with an N,N-diethylcarbamoyl group was efficiently catalyzed by an immobilized monophosphine-Ir system, which was prepared in situ from [Ir(OMe)(cod)](2) and a silica-supported, compact phosphine. The utility of the carbamoyloxy group as a leaving group for metal-catalyzed cross-coupling reactions was demonstrated by its utilization in the synthesis of a terphenyl derivative.
• Ruthenium-Catalyzed Carbonylative C–H Cyclization of 2-Arylphenols: A Novel Synthetic Route to 6<i>H</i>-Dibenzo[<i>b,d</i>]pyran-6-ones
  作者：Kiyofumi Inamoto、Jun Kadokawa、Yoshinori Kondo

  DOI：10.1021/ol401734m

  日期：2013.8.2

  Catalytic carbonylative C-H cyclization of 2-arylphenols can be achieved in the presence of a ruthenium-based catalytic system. The process proceeds efficiently under balloon pressure of CO and produces variously substituted 6H-dibenzo[b,d]pyran-6-one compounds, typically in good to high yields. Functional groups such as the alkoxycarbonyl and acetyl groups as well as halogen atoms (F, Cl, and Br) are well tolerated during the reaction.