(Z)-2-(hydroxyimino)-3-phenyl-2,3,6,7-tetrahydro benzofuran-4(5H)-one | 92774-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (Z)-2-(hydroxyimino)-3-phenyl-2,3,6,7-tetrahydro benzofuran-4(5H)-one
• 英文别名: (Z)-2-(hydroxyimino)-3-phenyl-2,3,6,7-tetrahydrobenzofuran-4(5H)-one；(2Z)-2-hydroxyimino-3-phenyl-3,5,6,7-tetrahydro-1-benzofuran-4-one
• CAS: 92774-92-0
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: VHQDEJKTZUTIGP-PFONDFGASA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  437.3±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  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 (Z)-2-(hydroxyimino)-3-phenyl-2,3,6,7-tetrahydro benzofuran-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

文献信息

• A mild and convenient one-pot two-step synthesis of hydroxy- iminodihydrobenzofurans mediated by silica gel under microwave activation conditions
  作者：Deepak Kumar Barange、B. Rama Raju、Veerababurao Kavala、Chun-Wei Kuo、Yu-Chen Tu、Ching-Fa Yao

  DOI：10.1016/j.tet.2010.03.051

  日期：2010.5

  A convenient one-pot two-step procedure for the synthesis of hydroxyiminodihydrobenzofurans assisted by microwave irradiation in presence of silica gel is described herein. Cyclic 1,3-dicarbonyl compounds reacted smoothly with various nitroolefins to furnish hydroxyiminodihydrobenzofuran derivatives as the mixture of E and Z isomers. Clean reaction conditions, no work-up procedure, easy isolation and

  本文描述了在硅胶存在下通过微波辐射辅助的羟基一亚氨基二氢苯并呋喃的便利的一锅两步法。环状1，3-二羰基化合物与各种硝基烯烃平稳反应，得到羟基亚氨基二氢苯并呋喃衍生物，为E和Z异构体的混合物。清洁的反应条件，无后处理程序，易于分离且产物收率高是该方法的主要特点。
• HRNCIAR, P.;CULAK, I., COLLECT. CZECH. CHEM. COMMUN., 1984, 49, N 6, 1421-1431
  作者：HRNCIAR, P.、CULAK, I.

  DOI：——

  日期：——
• 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.