2-bromo-8-(1-hydroxy-2-phenylethyl)dibenzofuran | 135892-94-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-bromo-8-(1-hydroxy-2-phenylethyl)dibenzofuran
• 英文别名: 1-(8-Bromodibenzofuran-2-yl)-2-phenylethanol
• CAS: 135892-94-3
• 化学式: C₂₀H₁₅BrO₂
• 分子量: 367.242
• InChiKey: AVYHMIXMXSWHET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-8-(1-hydroxy-2-phenylethyl)dibenzofuran 在 咪唑 、 乙基溴化镁 、 magnesium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 1-[8-[1-[Tert-butyl(dimethyl)silyl]oxy-2-phenylethyl]dibenzofuran-2-yl]ethanol
  参考文献：
  名称：

  Magnesium Methyl Carbonate-Activated Alkylation of Methyl Ketones with an ω-Halo Nitrile, Esters, and Amides

  摘要：

  Terminally substituted, extended-chain derivatives of the 2-dibenzofuranyl methyl ketone 6 and its phenylethyl analogue 12 were readily obtained by converting the ketones to magnesium chelates of their beta-carboxylated enolates with magnesium methyl carbonate (MMC, methyl methoxymagnesium carbonate, Stiles's reagent), followed by alkylation in situ with omega-halo compounds, X(CH2)(n)Y where X = Br and Y = CO(2)Me, CN, CONMe(2), CON(i-Pr)(2), CON(CH2)(4), or CON(CH2)(5) for n = 1; X = Br or I, and Y = CO(2)Me for n = 2; and X = Br and Y = CO(2)Me for n = 3. Dimethylcarbamoyl chloride (n = 0) gave products derived from MMC and the solvent, N,N-dimethylformamide. The order of reactivity of the halides was alpha > beta > gamma and beta-I > beta-Br. beta-Bromo amides were found to be unsuitable reactants. Lower reaction temperatures favored alkylation over competing elimination of HX from methyl beta-halopropionate. No self-condensation products of the ketones were observed; however, bis-alkylation and monomethylation products were formed when reaction times were prolonged. In contrast to the unsubstituted beta-keto acid 13, all intermediate alpha-alkyl beta-keto acids decarboxylated during the reaction or the workup.

  DOI：

  10.1021/jo960330v
• 作为产物：
  描述：

  2-溴二苯并呋喃 在 sodium tetrahydroborate 、 三氯化铝 作用下， 以 二硫化碳 、 水 、 异丙醇 为溶剂， 反应 1.0h， 生成 2-bromo-8-(1-hydroxy-2-phenylethyl)dibenzofuran
  参考文献：
  名称：

  Magnesium Methyl Carbonate-Activated Alkylation of Methyl Ketones with an ω-Halo Nitrile, Esters, and Amides

  摘要：

  Terminally substituted, extended-chain derivatives of the 2-dibenzofuranyl methyl ketone 6 and its phenylethyl analogue 12 were readily obtained by converting the ketones to magnesium chelates of their beta-carboxylated enolates with magnesium methyl carbonate (MMC, methyl methoxymagnesium carbonate, Stiles's reagent), followed by alkylation in situ with omega-halo compounds, X(CH2)(n)Y where X = Br and Y = CO(2)Me, CN, CONMe(2), CON(i-Pr)(2), CON(CH2)(4), or CON(CH2)(5) for n = 1; X = Br or I, and Y = CO(2)Me for n = 2; and X = Br and Y = CO(2)Me for n = 3. Dimethylcarbamoyl chloride (n = 0) gave products derived from MMC and the solvent, N,N-dimethylformamide. The order of reactivity of the halides was alpha > beta > gamma and beta-I > beta-Br. beta-Bromo amides were found to be unsuitable reactants. Lower reaction temperatures favored alkylation over competing elimination of HX from methyl beta-halopropionate. No self-condensation products of the ketones were observed; however, bis-alkylation and monomethylation products were formed when reaction times were prolonged. In contrast to the unsubstituted beta-keto acid 13, all intermediate alpha-alkyl beta-keto acids decarboxylated during the reaction or the workup.

  DOI：

  10.1021/jo960330v

文献信息

• Substituted dibenzofurans and methods of using same
  申请人：Euro-Celtique S.A.

  公开号：EP0422329A1

  公开（公告）日：1991-04-17

  Novel substituted dibenzofuran compounds are disclosed. The compounds exhibit activity in antagonizing the effects of leukotriene B₄ (LTB₄). Pharmaceutical compositions containing the novel compounds and methods of treatment employing the same are also described.

  本研究公开了新型取代二苯并呋喃化合物。这些化合物具有拮抗白三烯 B₄（LTB₄）作用的活性。此外，还描述了含有这种新型化合物的药物组合物以及使用这种化合物进行治疗的方法。
• US5019573A
  申请人：——

  公开号：US5019573A

  公开（公告）日：1991-05-28