(E)-3-(2,6-dimethoxyphenyl)allyl methyl carbonate | 1440140-30-6

• 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: (E)-3-(2,6-dimethoxyphenyl)allyl methyl carbonate
• CAS: 1440140-30-6
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: BLJQQBNRDIVAEV-AATRIKPKSA-N

物化性质

• 沸点：
  366.5±42.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,6-dimethoxyphenyl)allyl methyl carbonate 、 (Z)-methyl 3,3,3-trifluoro-2-(oxazolidin-2-ylidene)propanoate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以70%的产率得到(E)-methyl 2-(4,5-dihydrooxazol-2-yl)-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pent-4-enoate
  参考文献：
  名称：

  Palladium-catalyzed allylation of trifluoromethylated ketene aminoacetals

  摘要：

  A new development in the palladium-catalyzed allylation reaction of trifluoromethylated ketene aminoacetals was reported. These nucleophilic reagents were prepared by adding aminoalcohols to methyl 3,3,3-trifluoro-2-trifluoromethylpropanoate. The asymmetric version of the allylation reaction was investigated using chiral oxazolidine-based starting materials or chiral palladium catalysts. Asymmetric allylic alkylation was carried out with up to 74% ee using a chiral catalyst. However, no improvement was observed using double stereodifferentiation. These results provided a novel access for trifluoromethylated all-carbon quaternary carbon centers. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.10.002

文献信息

• Pd-Catalyzed Allylic Alkylation of CF3-Containing Esters with Three Electron-Withdrawing Groups
  作者：Yong Guo、Lun Li、Donghui Huang、Qing-Yun Chen

  DOI：10.1055/s-0032-1318313

  日期：——

  Tsuji-Trost reaction (Pd-catalyzed allylic alkylation) of CF3-containing esters with three electron-withdrawing groups is reported. The reactions with methyl bis(trifluoromethyl) acetate and dimethyl ( trifluoromethyl) malonate were carried out with low-loading catalysts of Pd(0) and XPhos at ambient temperature in THF, giving the products in high yields. This method efficiently overcomes the beta-defluorination, which is hard to control in the chemical transformation of alpha-trifluoromethyl carbanions, and provides versatile fluorinated compounds with quaternary carbon centers, which are highly demanded in drug discovery.