2-(3-(methoxymethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1245824-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-(methoxymethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 3-(Methoxymethoxy)phenylboronic Acid Pinacol Ester；2-[3-(methoxymethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1245824-36-5
• 化学式: C₁₄H₂₁BO₄
• 分子量: 264.129
• InChiKey: APHGOOVKGXBUOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(methoxymethoxy)aniline 在 bis(1,5-cyclooctadiene)nickel (0) 、 甲酸 、 potassium tert-butylate 、 sodium cyanoborohydride 、 1,3-二环己基氯化咪唑 作用下， 以 甲醇 、 乙二醇乙醚 、 甲苯 为溶剂， 反应 40.0h， 生成 2-(3-(methoxymethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C–N Bond Cleavage

  摘要：

  By developing a mild Ni-catalyzed system, a method for direct borylation of sp(2) and sp(3) C-N bonds has been established. The key to this hightly efficient C-N bond borylative cleavage depends on the appropriate choice of the nickel catalyst Ni(COD)(2), ICy center dot HCl as a ligand, and the use of 2-ethoxyethanol as the cosolvent. This transformation shows good functional group compatibility and can serve as powerful synthetic tool for gram-scale synthesis and late-stage C-N borylation of complex compounds.

  DOI：

  10.1021/acs.joc.5b02557

文献信息

• 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.
• Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C–N Bond Cleavage
  作者：Jiefeng Hu、Heqing Sun、Wangshui Cai、Xinghui Pu、Yemin Zhang、Zhuangzhi Shi

  DOI：10.1021/acs.joc.5b02557

  日期：2016.1.4

  By developing a mild Ni-catalyzed system, a method for direct borylation of sp(2) and sp(3) C-N bonds has been established. The key to this hightly efficient C-N bond borylative cleavage depends on the appropriate choice of the nickel catalyst Ni(COD)(2), ICy center dot HCl as a ligand, and the use of 2-ethoxyethanol as the cosolvent. This transformation shows good functional group compatibility and can serve as powerful synthetic tool for gram-scale synthesis and late-stage C-N borylation of complex compounds.