1-(4-bromo-3-nitrophenyl)-2,2-dimethylbut-3-en-1-ol

• 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: 1-(4-bromo-3-nitrophenyl)-2,2-dimethylbut-3-en-1-ol
• 化学式: C₁₂H₁₄BrNO₃
• 分子量: 300.152
• InChiKey: GWUCZNTZTMTYHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-1,2-丁二烯 、 4-溴-3-硝基苯甲醛 在 [Ir(cod)BIPHEP]B(3,5-(CF₃)2C₆H₃)4 氢气 、 lithium carbonate 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 以92%的产率得到1-(4-bromo-3-nitrophenyl)-2,2-dimethylbut-3-en-1-ol
  参考文献：
  名称：

  Carbonyl Allylation in the Absence of Preformed Allyl Metal Reagents:  Reverse Prenylation via Iridium-Catalyzed Hydrogenative Coupling of Dimethylallene

  摘要：

  Iridium-catalyzed hydrogenation of dimethylallene in the presence of aromatic, heteroaromatic, and aliphatic carbonyl electrophiles 1a-12a delivers products of reverse prenylation 1b-12b. Reductive coupling of dimethyl allene to aldehyde 8a under an atmosphere of deuterium provides deuterio -8b. As revealed by H-2 NMR analysis, deuterium incorporation is observed at the vinylic position (80% H-2). Unlike established methods for carbonyl allylation, the present protocol circumvents the use of stoichiometrically preformed organometallic reagents.

  DOI：

  10.1021/ja075971u

文献信息

• Carbonyl Allylation in the Absence of Preformed Allyl Metal Reagents:  Reverse Prenylation via Iridium-Catalyzed Hydrogenative Coupling of Dimethylallene
  作者：Eduardas Skucas、John F. Bower、Michael J. Krische

  DOI：10.1021/ja075971u

  日期：2007.10.1

  Iridium-catalyzed hydrogenation of dimethylallene in the presence of aromatic, heteroaromatic, and aliphatic carbonyl electrophiles 1a-12a delivers products of reverse prenylation 1b-12b. Reductive coupling of dimethyl allene to aldehyde 8a under an atmosphere of deuterium provides deuterio -8b. As revealed by H-2 NMR analysis, deuterium incorporation is observed at the vinylic position (80% H-2). Unlike established methods for carbonyl allylation, the present protocol circumvents the use of stoichiometrically preformed organometallic reagents.