1-furan-2-yl-pent-2-ene-1,4-dione | 52786-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-furan-2-yl-pent-2-ene-1,4-dione
• 英文别名: 1-(2-Furyl)-2-penten-1,4-dion
• CAS: 52786-26-2
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: YJMRJDHDFXDMJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.28
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-furan-2-yl-pent-2-ene-1,4-dione 、 丙二酸二甲酯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 dimethyl 2-(1-(furan-2-yl)-1,4-dioxopentan-3-yl)malonate
  参考文献：
  名称：

  CaCl₂, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction

  摘要：

  A mild protocol for the asymmetric Michael addition of dimethyl malonate to various alpha,beta-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl2, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl2 Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.

  DOI：

  10.1021/acs.joc.5b00769

文献信息

• Asymmetric Organocatalytic Aza-Michael Reactions of Isatin Derivatives
  作者：Tõnis Kanger、Sergei Žari、Andrus Metsala、Marina Kudrjashova、Sandra Kaabel、Ivar Järving

  DOI：10.1055/s-0034-1379956

  日期：——

  used as an aza-Michael donor in organocatalytic asymmetric reactions with symmetric and nonsymmetric unsaturated 1,4-diketones. After hydrolysis (in situ), the N-substituted isatins were obtained in high yields (up to >95%) with high enantioselectivity (up to 95%). Isatin was activated by derivatization to a Schiff base with aniline and used as an aza-Michael donor in organocatalytic asymmetric reactions

  摘要 Isatin通过与苯胺衍生为Schiff碱而被活化，并在与对称和非对称不饱和1,4-二酮的有机催化不对称反应中用作aza-Michael供体。水解后（原位），可以高收率（最高> 95％）和高对映选择性（最高95％）获得N-取代的靛红。 Isatin通过与苯胺衍生为Schiff碱而被活化，并在与对称和非对称不饱和1,4-二酮的有机催化不对称反应中用作aza-Michael供体。水解后（原位），可以高收率（最高> 95％）和高对映选择性（最高95％）获得N-取代的靛红。
• CaCl₂, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction
  作者：Kristin Lippur、Sandra Kaabel、Ivar Järving、Kari Rissanen、Tõnis Kanger

  DOI：10.1021/acs.joc.5b00769

  日期：2015.6.19

  A mild protocol for the asymmetric Michael addition of dimethyl malonate to various alpha,beta-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl2, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl2 Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.