(E)-2-(hydroxyimino)-3-(4-(trifluoromethyl)phenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one | 1291102-46-9

• 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)-2-(hydroxyimino)-3-(4-(trifluoromethyl)phenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one
• 英文别名: (2E)-2-hydroxyimino-3-[4-(trifluoromethyl)phenyl]-3,5,6,7-tetrahydro-1-benzofuran-4-one
• CAS: 1291102-46-9
• 化学式: C₁₅H₁₂F₃NO₃
• 分子量: 311.26
• InChiKey: ZQEOEUBGXIGYCL-XMHGGMMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 在 Porcine Pancreas Lipase 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 24.25h， 生成 (E)-2-(hydroxyimino)-3-(4-(trifluoromethyl)phenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one 、 (Z)-2-(hydroxyimino)-3-(4-(trifluoromethyl)phenyl)-2,3,6,7-tetrahydrobenzofuran-4(5H)-one
  参考文献：
  名称：

  A novel enzymatic tandem process: utilization of biocatalytic promiscuity for high stereoselective synthesis of 5-hydroxyimino-4,5-dihydrofurans

  摘要：

  A lipase-catalyzed protocol for the synthesis of 5-hydroxyimino-4,5-dihydrofurans via tandem coupling between beta-nitrostyrenes and 1,3-dicarbonyl compounds was developed in a 'one-pot' strategy. A series of beta-nitrostyrenes were employed to expand the scope of this new biocatalytic promiscuity with high stereoselectivity (Z/E up to 99:1) and moderate to good yields. The reaction activity of 1,3-cyclo-hexanedione was found to be better than linear 2,4-pentanedione, while ethyl acetoacetate and diethylmalonate were not suitable for this reaction under the same conditions. Single-crystal X-ray diffraction analysis indicated that the reaction was stereoselective and Z-stereomer was found to be the major product. A reaction mechanism was supposed to elucidate the biocatalytic process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.060