p-chlorocinnamaldehyde diethylacetal | 106485-15-8

• 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: p-chlorocinnamaldehyde diethylacetal
• 英文别名: p-Chlorzimtaldehyd-diethylacetal；1-chloro-4-(3,3-diethoxyprop-1-enyl)benzene
• CAS: 106485-15-8；36382-36-2
• 化学式: C₁₃H₁₇ClO₂
• 分子量: 240.73
• InChiKey: YMGBSMSHQYCJKG-UHFFFAOYSA-N

物化性质

• 沸点：
  328.7±42.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  p-chlorocinnamaldehyde diethylacetal 在 盐酸 、 potassium chloride 、 四丁基醋酸铵 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 0.17h， 生成 4-chlorocinnamaldehyde
  参考文献：
  名称：

  Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium

  摘要：

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.

  DOI：

  10.1021/jo202482h
• 作为产物：
  描述：

  对氯碘苯 、 丙烯醛缩二乙醇 在 C₇₀H₄₀Cl₂F₆₈N₂O₆Pd₂ 、 potassium chloride 、 四丁基醋酸铵 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.02h， 生成 p-chlorocinnamaldehyde diethylacetal
  参考文献：
  名称：

  Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium

  摘要：

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.

  DOI：

  10.1021/jo202482h

文献信息

• Hydroformylation of cinnamic acid derivatives catalysed by rhodium complexes
  作者：C. Botteghi、S. Paganelli

  DOI：10.1016/0022-328x(93)83039-x

  日期：1993.6

  The hydroformylation of methyl cinnamate catalysed by various rhodium complexes affords the aldehyde 1a with good chemo- and regio-selectivity, while in the case of methyl p-chlorocinnamate the predominant reaction is the substrate hydrogenation. Higher yields of the desired aldehydes 1a and 1b are obtained by hydroformylation of the cinnamaldehyde and p-chlorocinnamaldehyde diethylacetal, respectively

  通过各种铑络合物催化的肉桂酸甲酯的羰基化，得到醛1A具有良好的化疗和区域选择性，而在甲基的情况下，p -chlorocinnamate主要反应是衬底氢化。在相同的反应条件下，通过肉桂醛和对氯肉桂醛二乙缩醛的加氢甲酰化反应，可以得到更高产率的所需醛1a和1b。这些醛产物是有价值的药物前体。
• Ungesättigte Oxime, 27. Mitt. 5-Phenyl-2.4-pentadienale und ihre Oxime
  作者：Bernard Unterhalt、Sulaiman Eljabour、Hildegard Milsmann

  DOI：10.1002/ardp.19863191213

  日期：——

  4‐pentadienale 3a–f werden aus den 3‐Phenyl‐propenal‐diethylacetalen la–f und Ethylvinylether dargestellt und ihre Oxime 4a–f in die (E)‐ und (Z)‐Isomere getrennt. Beim Einsatz der α‐verzweigten 5‐Phenyl‐2,4‐pentadienale 5a–d, die durch Aldolkondensation gewonnen werden, sind die einheitlichen (E)‐Oxime 6a–d zu erhalten.

  5-苯基-2,4-戊二烯醛3a-f由3-苯基-丙烯醛-二乙缩醛la-f和乙基乙烯基醚制备，它们的肟4a-f被分离成(E)和(Z)异构体。当使用α-支链5-苯基-2,4-戊二烯醛5a-d时，它们是通过羟醛缩合得到的，可以得到均匀的(E)-肟6a-d。