2-methoxyphenyl methyl ketene | 463299-71-0

• 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: 2-methoxyphenyl methyl ketene
• 英文别名: o-methoxyphenyl methyl ketene；o-anisyl methyl ketene
• CAS: 463299-71-0
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: DXEZFYLYHPUNTF-UHFFFAOYSA-N

物化性质

• 沸点：
  226.0±9.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxyphenyl methyl ketene 在 lithium aluminium tetrahydride 、 chiral (-)-ferrocene catalyst 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  乙烯酮与醛的催化不对称偶联，生成烯醇酯。

  摘要：

  DOI：

  10.1002/anie.200501434
• 作为产物：
  描述：

  2-(2-methoxyphenyl)propionyl chloride 在 二甲基十二/十四烷基叔胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以42%的产率得到2-methoxyphenyl methyl ketene
  参考文献：
  名称：

  Enantioselective Addition of Amines to Ketenes Catalyzed by a Planar-Chiral Derivative of PPY:  Possible Intervention of Chiral Brønsted-Acid Catalysis

  摘要：

  The first method for the catalytic enantioselective addition of amines (specifically, pyrroles) to ketenes has been developed, and it has been demonstrated that the resulting acylpyrroles can be transformed into a broad spectrum of useful derivatives. On the basis of mechanistic studies, it is suggested that the planar-chiral catalyst plays an unanticipated role in this process as a chiral Brønsted acid.

  DOI：

  10.1021/ja027466x

文献信息

• Catalytic Asymmetric Synthesis of Esters from Ketenes
  作者：Sheryl L. Wiskur、Gregory C. Fu

  DOI：10.1021/ja0506152

  日期：2005.5.1

  By building on elementary principles of Brønsted acid-base chemistry, a nucleophile-catalyzed method for the asymmetric synthesis of esters from ketenes has been transformed into a much more versatile and effective Brønsted acid-catalyzed process. The product aryl esters can be converted into useful derivatives, such as enantioenriched alcohols and carboxylic acids.

  通过建立在布朗斯台德酸碱化学基本原理的基础上，从烯酮不对称合成酯的亲核试剂催化方法已转变为更通用和有效的布朗斯台德酸催化工艺。产物芳基酯可以转化为有用的衍生物，例如对映体富集的醇和羧酸。
• Dochnahl, Maximilian; Fu, Gregory C., Angewandte Chemie - International Edition, 2009, vol. 48, p. 2391 - 2393
  作者：Dochnahl, Maximilian、Fu, Gregory C.

  DOI：——

  日期：——
• Enantioselective Synthesis of Protected Amines by the Catalytic Asymmetric Addition of Hydrazoic Acid to Ketenes
  作者：Xing Dai、Takashi Nakai、Jan A. C. Romero、Gregory C. Fu

  DOI：10.1002/anie.200700697

  日期：2007.6.4
• Catalytic Asymmetric Couplings of Ketenes with Aldehydes To Generate Enol Esters
  作者：Carsten Schaefer、Gregory C. Fu

  DOI：10.1002/anie.200501434

  日期：2005.7.18
• Enantioselective Addition of Amines to Ketenes Catalyzed by a Planar-Chiral Derivative of PPY:  Possible Intervention of Chiral Brønsted-Acid Catalysis
  作者：Brian L. Hodous、Gregory C. Fu

  DOI：10.1021/ja027466x

  日期：2002.8.1

  The first method for the catalytic enantioselective addition of amines (specifically, pyrroles) to ketenes has been developed, and it has been demonstrated that the resulting acylpyrroles can be transformed into a broad spectrum of useful derivatives. On the basis of mechanistic studies, it is suggested that the planar-chiral catalyst plays an unanticipated role in this process as a chiral Brønsted acid.