(Z)-1-(2'-(hydroxyimino)-5'-methyl-2',3'-dihydro-[2,3'-bifuran]-4'-yl)ethanone | 1291102-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (Z)-1-(2'-(hydroxyimino)-5'-methyl-2',3'-dihydro-[2,3'-bifuran]-4'-yl)ethanone
• 英文别名: 1-[(2Z)-3-(furan-2-yl)-2-hydroxyimino-5-methyl-3H-furan-4-yl]ethanone
• CAS: 1291102-44-7
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: AIADTPLYMMBGDO-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  糠醛 在 Porcine Pancreas Lipase 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 48.25h， 生成 (Z)-1-(2'-(hydroxyimino)-5'-methyl-2',3'-dihydro-[2,3'-bifuran]-4'-yl)ethanone
  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

文献信息

• A novel enzymatic tandem process: utilization of biocatalytic promiscuity for high stereoselective synthesis of 5-hydroxyimino-4,5-dihydrofurans
  作者：Ming-Yu Wu、Kun Li、Ting He、Xing-Wen Feng、Na Wang、Xiao-Yan Wang、Xiao-Qi Yu

  DOI：10.1016/j.tet.2011.01.060

  日期：2011.4

  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.