2-(4-methoxy-2,3,5,6-tetramethylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane | 1208459-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxy-2,3,5,6-tetramethylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
• 英文别名: 2-(4-Methoxy-2,3,5,6-tetramethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-(4-methoxy-2,3,5,6-tetramethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1208459-66-8
• 化学式: C₁₇H₂₇BO₃
• 分子量: 290.211
• InChiKey: JWEBQYRIXHRSBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-methoxy-2,3,5,6-tetramethylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 在 lithium aluminium tetrahydride 、 Glauber's salt 、 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以68%的产率得到(4-methoxy-2,3,5,6-tetramethyl)-phenyl boronic acid
  参考文献：
  名称：

  Syntheses of extreme sterically hindered 4-methoxyboronic acids

  摘要：

  4-Iodoanisoles 3a,b, 3d and 4-bromoanisoles 4a-d were readily obtained. An extreme steric hindrance precluded obtaining 3c. Catalytic borylation of 3a,b, 3d followed by hydrolysis of boronic ester 26a,b, 26d easily provided the boronic acids 5a,b, 5d. Compounds Sa and 5d were also synthesised, starting from 4a and 4d, by halogen/metal exchange. Because of a too important steric hindrance, this last reaction failed with 4c and 4b led to the unexpected but stable boronic ester 6. The final obtaining of 5b required a strongly basic hydrolysis with heating. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.103
• 作为产物：
  描述：

  1-碘-4-甲氧基-2,3,5,6-四甲基苯 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 以72%的产率得到2-(4-methoxy-2,3,5,6-tetramethylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
  参考文献：
  名称：

  Syntheses of extreme sterically hindered 4-methoxyboronic acids

  摘要：

  4-Iodoanisoles 3a,b, 3d and 4-bromoanisoles 4a-d were readily obtained. An extreme steric hindrance precluded obtaining 3c. Catalytic borylation of 3a,b, 3d followed by hydrolysis of boronic ester 26a,b, 26d easily provided the boronic acids 5a,b, 5d. Compounds Sa and 5d were also synthesised, starting from 4a and 4d, by halogen/metal exchange. Because of a too important steric hindrance, this last reaction failed with 4c and 4b led to the unexpected but stable boronic ester 6. The final obtaining of 5b required a strongly basic hydrolysis with heating. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.103

文献信息

• Syntheses of extreme sterically hindered 4-methoxyboronic acids
  作者：Vincent Diemer、Hélène Chaumeil、Albert Defoin、Christiane Carré

  DOI：10.1016/j.tet.2009.11.103

  日期：2010.1

  4-Iodoanisoles 3a,b, 3d and 4-bromoanisoles 4a-d were readily obtained. An extreme steric hindrance precluded obtaining 3c. Catalytic borylation of 3a,b, 3d followed by hydrolysis of boronic ester 26a,b, 26d easily provided the boronic acids 5a,b, 5d. Compounds Sa and 5d were also synthesised, starting from 4a and 4d, by halogen/metal exchange. Because of a too important steric hindrance, this last reaction failed with 4c and 4b led to the unexpected but stable boronic ester 6. The final obtaining of 5b required a strongly basic hydrolysis with heating. (C) 2009 Elsevier Ltd. All rights reserved.