5-methoxy-1-triethylsilyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene | 1160553-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-methoxy-1-triethylsilyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
• 英文别名: Triethyl-[5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane；triethyl-[5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane
• CAS: 1160553-84-3
• 化学式: C₁₉H₃₃BO₃Si
• 分子量: 348.366
• InChiKey: QAURRYOENZNMTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  5-methoxy-1-triethylsilyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene 在 三溴化硼 、 水 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 以93%的产率得到(3-hydroxyphenyl)triethylsilane
  参考文献：
  名称：

  히드록시아렌 붕소산 화합물의 열적 탈붕소수소화 및 이를 이용하여 페놀계 화합물의 오르소 또는 메타 위치에 작용기를 도입시킨 히드록시아렌 화합물의 제조방법

  摘要：

  This invention relates to a method for producing hydroxyarenes with introduced functional groups at the ortho or meta positions of phenolic compounds using the thermal deboronation of hydroxyarene boronic acid compounds. More specifically, the method involves substituting the ortho or para positions of phenol with boronic acid, introducing functional groups at the ortho or meta positions to produce hydroxyarene boronic acid compounds, and removing the boronic acid using thermal deboronation to obtain hydroxyarene compounds with functional groups at the ortho or meta positions. The method for producing hydroxyarene compounds according to this invention does not require metal catalysts such as palladium or iridium and does not involve harsh conditions such as strong acid or base, low temperature reactions, or anhydrous conditions, making it economical and simple to produce hydroxyarene compounds with functional groups at the ortho or meta positions from phenol.

  公开号：

  KR101572521B1
• 作为产物：
  描述：

  三乙基硅烷 在 对甲苯磺酸 、 2-(1H-3-吡唑)苯胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成 5-methoxy-1-triethylsilyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
  参考文献：
  名称：

  히드록시아렌 붕소산 화합물의 열적 탈붕소수소화 및 이를 이용하여 페놀계 화합물의 오르소 또는 메타 위치에 작용기를 도입시킨 히드록시아렌 화합물의 제조방법

  摘要：

  This invention relates to a method for producing hydroxyarenes with introduced functional groups at the ortho or meta positions of phenolic compounds using the thermal deboronation of hydroxyarene boronic acid compounds. More specifically, the method involves substituting the ortho or para positions of phenol with boronic acid, introducing functional groups at the ortho or meta positions to produce hydroxyarene boronic acid compounds, and removing the boronic acid using thermal deboronation to obtain hydroxyarene compounds with functional groups at the ortho or meta positions. The method for producing hydroxyarene compounds according to this invention does not require metal catalysts such as palladium or iridium and does not involve harsh conditions such as strong acid or base, low temperature reactions, or anhydrous conditions, making it economical and simple to produce hydroxyarene compounds with functional groups at the ortho or meta positions from phenol.

  公开号：

  KR101572521B1

文献信息

• Protodeboronation of ortho- and para-Phenol Boronic Acids and Application to ortho and meta Functionalization of Phenols Using Boronic Acids as Blocking and Directing Groups
  作者：Chun-Young Lee、Su-Jin Ahn、Cheol-Hong Cheon

  DOI：10.1021/jo402174v

  日期：2013.12.6

  The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by sigma-bond metathesis.
• Ihara, Hideki; Suginome, Michinori, Journal of the American Chemical Society, 2009, vol. 131, p. 7502 - 7503
  作者：Ihara, Hideki、Suginome, Michinori

  DOI：——

  日期：——