Ethyl 2-cyano-3-(2,6-difluorophenyl)prop-2-enoate | 790227-40-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Ethyl 2-cyano-3-(2,6-difluorophenyl)prop-2-enoate
• CAS: 790227-40-6
• 化学式: C₁₂H₉F₂NO₂
• mdl: MFCD06227780
• 分子量: 237.206
• InChiKey: RJAFFRWNZYGWBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-cyano-3-(2,6-difluorophenyl)prop-2-enoate 、 硫脲 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 、
  参考文献：
  名称：

  Some Observations on the Base-Catalyzed Cyclocondensation of 2,6-Dihalobenzaldehydes, Ethyl Cyanoacetate, and Thiourea

  摘要：

  The reaction of 2,6-difluorobenzaldehyde, 2-chloro-6-fluorobenzaldehyde, or 2,6-dichlorobenzaldehyde and ethyl cyanoacetate and thiourea, in the presence of potassium carbonate, yielded a mixture of the cis- and trans-5,6-dihydro-2-thiouracil derivatives 4a-c. Compounds 4a-c, which were found to be resistant to atmospheric oxidation even at high temperatures, were successfully dehydrogenated to 5a-c via prolonged heating with chloranil in toluene. Meanwhile, oxidation of the dihydro derivative 4b by heating in dimethylsufphoxide for 10min yielded the corresponding 2-thiouracil 5b in 73% yield, in addition to the disulfide derivative 7 as a minor product.

  DOI：

  10.1080/00397910903098730
• 作为产物：
  描述：

  2,6-二氟苯甲醛 、 氰乙酸乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 Ethyl 2-cyano-3-(2,6-difluorophenyl)prop-2-enoate
  参考文献：
  名称：

  Some Observations on the Base-Catalyzed Cyclocondensation of 2,6-Dihalobenzaldehydes, Ethyl Cyanoacetate, and Thiourea

  摘要：

  The reaction of 2,6-difluorobenzaldehyde, 2-chloro-6-fluorobenzaldehyde, or 2,6-dichlorobenzaldehyde and ethyl cyanoacetate and thiourea, in the presence of potassium carbonate, yielded a mixture of the cis- and trans-5,6-dihydro-2-thiouracil derivatives 4a-c. Compounds 4a-c, which were found to be resistant to atmospheric oxidation even at high temperatures, were successfully dehydrogenated to 5a-c via prolonged heating with chloranil in toluene. Meanwhile, oxidation of the dihydro derivative 4b by heating in dimethylsufphoxide for 10min yielded the corresponding 2-thiouracil 5b in 73% yield, in addition to the disulfide derivative 7 as a minor product.

  DOI：

  10.1080/00397910903098730

文献信息

• Polyoxometalate-Intercalated Layered Double Hydroxides as Efficient and Recyclable Bifunctional Catalysts for Cascade Reactions
  作者：Kai Liu、Yanqi Xu、Zhixiao Yao、Haralampos N. Miras、Yu-Fei Song

  DOI：10.1002/cctc.201501365

  日期：2016.3.7

  heterogeneous catalysts. However, the application of POM–LDHs as bifunctional catalysts for cascade reaction has seldom been studied compared to the noble‐metal‐based catalysts. Herein, a series of POM–LDHs catalysts of Tris–LDH–X4(PW9)2 (X=Mn, Fe, Co, Ni, Cu, and Zn; Tris=Tris(hydroxymethtyl)aminomethane) have been prepared. The efficacy of Tris–LDH–Zn4(PW9)2 as efficient bifunctional catalyst has been

  多金属氧酸盐（POM）插层的双氢氧化物（LDHs）已被广泛用作非均相催化剂。但是，与基于贵金属的催化剂相比，很少研究将POM-LDHs作为双功能催化剂用于级联反应。在此，制备了一系列的Tris–LDH–X 4（PW 9）2（X = Mn，Fe，Co，Ni，Cu和Zn； Tris = Tris（羟甲基）氨基甲烷）POM-LDHs催化剂。Tris–LDH–Zn 4（PW 9）2的功效由于已经证明有效的双功能催化剂用于级联反应，该级联反应包括将苄醇氧化为苯甲醛，然后与氰乙酸乙酯进行Knoevenagel缩合以生成亚苄基氰乙酸乙酯。POM的氧化还原/酸性位点和LDHs的碱性位点的组合导致在温和无碱条件下具有优异活性（99％）和选择性（≥99％）的复合催化剂。这项工作为高效双功能催化剂的制备提供了一种新的设计策略，以促进一锅级联反应。