4-ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene | 153862-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene
• 英文别名: 4-(4-ethyl-1-hydroxy-2,1-benzoxaborinin-3-yl)phenol
• CAS: 153862-14-7
• 化学式: C₁₆H₁₅BO₃
• 分子量: 266.104
• InChiKey: UUMNWUNZIIMNME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene 在 NaOH 、 H₂O₂ 、 HCl 作用下， 以 水 为溶剂， 以100%的产率得到1-(4-hydroxyphenyl)-2-(2-hydroxyphenyl)-butan-1-one
  参考文献：
  名称：

  ortho-Directed electrophilic boronation of a benzyl ketone: the preparation, X-ray crystal structure, and some reactions of 4-ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene

  摘要：

  4-Ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene (4) is formed in 78% yield from the reaction of 1-(4-metho-xyphenyl)-2-phenylbutan-1-one with an of excess boron tribromide in dichloromethane followed by treatment with water. Reaction of 4 with iodine in aqueous sodium hydroxide gives a second oxaboracycle, 3-ethyl-1-hydroxy-3-(4-hydroxybenzoyl)-2,1-benzo-xaborolane (5). The X-ray crystal structure determinations of both boron heterocycles are reported. Other new compounds reported are 1-(4-hydroxyphenyl)-2-(1-hydroxyphenyl)-butan-1-one (6), formed by reaction of 4 with alkaline hydrogen peroxide, and 1-(4-hydroxyphenyl)-2-(2-biphenyl)-butan-1-one (8), formed by coupling of 4 with bromobenzene in the presence of Pd(PPh(3))(4).

  DOI：

  10.1016/0022-328x(93)83139-m
• 作为产物：
  描述：

  1-(4-甲氧基苯基)-2-苯基-1-丁酮 、 三溴化硼 以 二氯甲烷 为溶剂， 以78%的产率得到4-ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene
  参考文献：
  名称：

  ortho-Directed electrophilic boronation of a benzyl ketone: the preparation, X-ray crystal structure, and some reactions of 4-ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene

  摘要：

  4-Ethyl-1-hydroxy-3-(4-hydroxyphenyl)-2-oxa-1-boranaphthalene (4) is formed in 78% yield from the reaction of 1-(4-metho-xyphenyl)-2-phenylbutan-1-one with an of excess boron tribromide in dichloromethane followed by treatment with water. Reaction of 4 with iodine in aqueous sodium hydroxide gives a second oxaboracycle, 3-ethyl-1-hydroxy-3-(4-hydroxybenzoyl)-2,1-benzo-xaborolane (5). The X-ray crystal structure determinations of both boron heterocycles are reported. Other new compounds reported are 1-(4-hydroxyphenyl)-2-(1-hydroxyphenyl)-butan-1-one (6), formed by reaction of 4 with alkaline hydrogen peroxide, and 1-(4-hydroxyphenyl)-2-(2-biphenyl)-butan-1-one (8), formed by coupling of 4 with bromobenzene in the presence of Pd(PPh(3))(4).

  DOI：

  10.1016/0022-328x(93)83139-m