4-Bromo-2-(bromomethyl)-1-prop-1-ynylbenzene | 1104877-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Bromo-2-(bromomethyl)-1-prop-1-ynylbenzene
• CAS: 1104877-42-0
• 化学式: C₁₀H₈Br₂
• 分子量: 287.982
• InChiKey: YIOLMWJPGYRHAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-碘苯酚 、 4-Bromo-2-(bromomethyl)-1-prop-1-ynylbenzene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以64.7 g的产率得到4-溴-2-(2-碘-苯氧基)甲基-1-(丙-1-炔基)苯
  参考文献：
  名称：

  Development of an Efficient Palladium-Catalyzed Intramolecular Carbometalation Reaction for the Synthesis of a Dibenzoxapine Containing Tetra-substituted Exocyclic Alkene

  摘要：

  A practical and scaleable synthesis of (Z)-3-(1-(8-bromodibenzo[b,e]oxepin-11(6H)-ylidene)ethyl)aniline hydrochloride (1 center dot HCl), a key intermediate in the synthesis of a selective nuclear hormone receptor modulator, Is described. The target compound is prepared in five steps from commercially available (5-bromo-2-iodophenyl)-methanol (5) with a 47% overall yield. The key step involves a palladium-catalyzed intramolecular carbometalation of an alkyne, which affords the dibenzoxapine containing tetrasubstituted exocyclic alkene framework stereoselectively in a single step from readily available building blocks 4-bromo-2-(2-iodo-phenoxymethyl )-1-prop-1-ynyl-benzene (3) and 3-nitrophenylboronic acid (4). The development of each step is described. The main focus of the paper is the description and optimization of the intramolecular carbometalation of an alkyne. Eventually, the target compound 1 center dot HCl was prepared in multikilogram quantities with >97% purity.

  DOI：

  10.1021/op800231b
• 作为产物：
  描述：

  (5-bromo-2-prop-1-ynyl-phenyl)methanol 在 三溴化磷 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 4-Bromo-2-(bromomethyl)-1-prop-1-ynylbenzene
  参考文献：
  名称：

  Development of an Efficient Palladium-Catalyzed Intramolecular Carbometalation Reaction for the Synthesis of a Dibenzoxapine Containing Tetra-substituted Exocyclic Alkene

  摘要：

  A practical and scaleable synthesis of (Z)-3-(1-(8-bromodibenzo[b,e]oxepin-11(6H)-ylidene)ethyl)aniline hydrochloride (1 center dot HCl), a key intermediate in the synthesis of a selective nuclear hormone receptor modulator, Is described. The target compound is prepared in five steps from commercially available (5-bromo-2-iodophenyl)-methanol (5) with a 47% overall yield. The key step involves a palladium-catalyzed intramolecular carbometalation of an alkyne, which affords the dibenzoxapine containing tetrasubstituted exocyclic alkene framework stereoselectively in a single step from readily available building blocks 4-bromo-2-(2-iodo-phenoxymethyl )-1-prop-1-ynyl-benzene (3) and 3-nitrophenylboronic acid (4). The development of each step is described. The main focus of the paper is the description and optimization of the intramolecular carbometalation of an alkyne. Eventually, the target compound 1 center dot HCl was prepared in multikilogram quantities with >97% purity.

  DOI：

  10.1021/op800231b

文献信息

• Development of an Efficient Palladium-Catalyzed Intramolecular Carbometalation Reaction for the Synthesis of a Dibenzoxapine Containing Tetra-substituted Exocyclic Alkene
  作者：Rachel N. Richey、Hannah Yu

  DOI：10.1021/op800231b

  日期：2009.3.20

  A practical and scaleable synthesis of (Z)-3-(1-(8-bromodibenzo[b,e]oxepin-11(6H)-ylidene)ethyl)aniline hydrochloride (1 center dot HCl), a key intermediate in the synthesis of a selective nuclear hormone receptor modulator, Is described. The target compound is prepared in five steps from commercially available (5-bromo-2-iodophenyl)-methanol (5) with a 47% overall yield. The key step involves a palladium-catalyzed intramolecular carbometalation of an alkyne, which affords the dibenzoxapine containing tetrasubstituted exocyclic alkene framework stereoselectively in a single step from readily available building blocks 4-bromo-2-(2-iodo-phenoxymethyl )-1-prop-1-ynyl-benzene (3) and 3-nitrophenylboronic acid (4). The development of each step is described. The main focus of the paper is the description and optimization of the intramolecular carbometalation of an alkyne. Eventually, the target compound 1 center dot HCl was prepared in multikilogram quantities with >97% purity.