4-Methoxy-I(3)-methylbenzenebutanal | 127047-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Methoxy-I(3)-methylbenzenebutanal
• 英文别名: 4-(4-methoxyphenyl)pentanal
• CAS: 127047-18-1
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: LULKTSZCYZNQMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  顺-3-戊烯-1-醇 、 4-甲氧基苯硼酸 在 Pd(CH₃CN)2(OTs)2 、 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-Methoxy-I(3)-methylbenzenebutanal
  参考文献：
  名称：

  Enantioselective Redox-Relay Oxidative Heck Arylations of Acyclic Alkenyl Alcohols using Boronic Acids

  摘要：

  A general, highly selective asymmetric redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acid derivatives is reported. This reaction delivers remotely functionalized arylated carbonyl products from acyclic alkenol substrates, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. A preliminary mechanistic investigation suggests that the regioselectivity of the initial migratory insertion is highly dependent on the electronic nature of the boronic acid and more subtle electronic effects of the alkenyl alcohol.

  DOI：

  10.1021/ja402916z

文献信息

• Synthesis of aryl-substituted aldehydes and ketones via palladium-catalyzed coupling of aryl halides and non-allylic unsaturated alcohols
  作者：Richard C. Larock、Wai-Yee Leung、Sandra Stolz-Dunn

  DOI：10.1016/s0040-4039(00)70636-8

  日期：——

  The palladium-catalyzed coupling of aryl halides and non-allylic unsaturated alcohols affords excellent yields of aryl-substituted aldehydes and ketones.

  芳基卤化物和非烯丙基不饱和醇的钯催化偶联提供了芳基取代的醛和酮的优异收率。
• LAROCK, RICHARD C.;LAUND, WAI-YEE;STOLZ-DUNN, SANDRA, TETRAHEDRON LETT., 30,(1989) N8, C. 6629-6632
  作者：LAROCK, RICHARD C.、LAUND, WAI-YEE、STOLZ-DUNN, SANDRA

  DOI：——

  日期：——
• Enantioselective Redox-Relay Oxidative Heck Arylations of Acyclic Alkenyl Alcohols using Boronic Acids
  作者：Tian-Sheng Mei、Erik W. Werner、Alexander J. Burckle、Matthew S. Sigman

  DOI：10.1021/ja402916z

  日期：2013.5.8

  A general, highly selective asymmetric redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acid derivatives is reported. This reaction delivers remotely functionalized arylated carbonyl products from acyclic alkenol substrates, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. A preliminary mechanistic investigation suggests that the regioselectivity of the initial migratory insertion is highly dependent on the electronic nature of the boronic acid and more subtle electronic effects of the alkenyl alcohol.