2-bromo-8-[1-hydroxy-2-(2-phenylethyl)phenylethyl]dibenzofuran | 185981-48-0

• 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-(2-phenylethyl)phenylethyl]dibenzofuran
• 英文别名: 1-(8-Bromodibenzofuran-2-yl)-2-[2-(2-phenylethyl)phenyl]ethanol
• CAS: 185981-48-0
• 化学式: C₂₈H₂₃BrO₂
• 分子量: 471.393
• InChiKey: OPYAHRWRXPPAOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 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-(2-phenylethyl)phenylethyl]dibenzofuran 在 咪唑 、 aluminum oxide 、 乙基溴化镁 、 magnesium 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.33h， 生成 1-[8-[1-[Tert-butyl(dimethyl)silyl]oxy-2-[2-(2-phenylethyl)phenyl]ethyl]dibenzofuran-2-yl]ethanone
  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：

  1-(8-Bromo-dibenzofuran-2-yl)-2-(2-phenethyl-phenyl)-ethanone 在 sodium tetrahydroborate 作用下， 以 水 、 异丙醇 为溶剂， 反应 1.0h， 以98%的产率得到2-bromo-8-[1-hydroxy-2-(2-phenylethyl)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

• Magnesium Methyl Carbonate-Activated Alkylation of Methyl Ketones with an ω-Halo Nitrile, Esters, and Amides
  作者：Elli S. Hand、Stephen C. Johnson、David C. Baker

  DOI：10.1021/jo960330v

  日期：1997.3.1

  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.