1-(3-methoxyphenyl)dodecan-1-one | 63442-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-methoxyphenyl)dodecan-1-one
• 英文别名: m-Methoxy-laurylbenzol；1-(3-Methoxyphenyl)dodecan-1-one
• CAS: 63442-83-1
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: YEJVXCMFWMHDEE-UHFFFAOYSA-N

物化性质

• 沸点：
  390.9±15.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  3-甲氧基苯硼酸 、 S-(4-bromobutyl) dodecanethioate 在 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以50%的产率得到1-(3-methoxyphenyl)dodecan-1-one
  参考文献：
  名称：

  Thiol Ester−Boronic Acid Cross-Coupling. Catalysis Using Alkylative Activation of the Palladium Thiolate Intermediate

  摘要：

  [GRAPHICS]Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-nbutyl thiol esters were most effective in this cross-coupling.

  DOI：

  10.1021/ol000231a

文献信息

• A general method for the direct transformation of common tertiary amides into ketones and amines by addition of Grignard reagents
  作者：Pei-Qiang Huang、Yu Wang、Kai-Jiong Xiao、Ying-Hong Huang

  DOI：10.1016/j.tet.2015.04.074

  日期：2015.6

  organometallic reagents has attracted the attention of organic chemists for a long time. However limited methods are reliable for common amides and have found synthetic applications. Here we report a method featuring in situ activation of tertiary amides with triflic anhydride (Tf2O) followed by addition of Grignard reagents. The method displays a good generality in scope for both amides and Grignard reagents

  通过添加有机金属试剂将酰胺直接转化为酮已引起有机化学家的长期关注。然而，有限的方法对于常见的酰胺是可靠的并且已经发现了合成应用。在这里我们报告了一种方法，其特征是用三氟甲磺酸酐（Tf 2 O）原位活化叔酰胺，然后加入格氏试剂。该方法在酰胺和格利雅试剂上都显示出良好的通用性，可以看作是使用酰胺作为稳定和选择性的酰化剂对格利雅试剂进行的酰化反应。而且，该脱氨基烷基化反应提供了一种温和的方法，用于酰胺的N-脱酰作用以得到游离的胺。
• Thiol Ester−Boronic Acid Cross-Coupling. Catalysis Using Alkylative Activation of the Palladium Thiolate Intermediate
  作者：Cecile Savarin、Jiri Srogl、Lanny S. Liebeskind

  DOI：10.1021/ol000231a

  日期：2000.10.1

  [GRAPHICS]Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-nbutyl thiol esters were most effective in this cross-coupling.