3-Benzofuranol, 2,3-dihydro-2-nitro-, trans- | 104412-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-Benzofuranol, 2,3-dihydro-2-nitro-, trans-
• 英文别名: c-3-hydroxy-r-2-nitro-2,3-dihydrobenzofuran；t-3-hydroxy-r-2-nitro-2,3-dihydrobenzofuran
• CAS: 104412-83-1；104412-91-1
• 化学式: C₈H₇NO₄
• 分子量: 181.148
• InChiKey: WCBXEXXAHLOLTH-YUMQZZPRSA-N

物化性质

• 沸点：
  360.9±42.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  溴代硝基甲烷 、 水杨醛 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 c-3-hydroxy-r-2-nitro-2,3-dihydrobenzofuran 、 3-Benzofuranol, 2,3-dihydro-2-nitro-, trans-
  参考文献：
  名称：

  An Improved Synthesis of 2-Nitrobenzo[b]furans

  摘要：

  通过在低温下将邻羟基苯甲醛1与溴硝基甲烷2反应，以避免在碱性缩合介质中脱水，从而提高2-硝基苯并[b]呋喃4的产率。随后，通过在乙酸酐中加热，该醛醇中间体3可定量脱水。

  DOI：

  10.1055/s-1985-31435

文献信息

• Photochemical Nitration by Tetranitromethane. Part XL. Regiochemistry of Trinitromethyl Attachment in the Photolysis of Benzofuran with Tetranitromethane.
  作者：Craig P. Butts、Lennart Eberson、Remedios Gonzáles-Luque、Chris M. Hartshorn、Michael P. Hartshorn、Manuela Merchán、Ward T. Robinson、Björn O. Roos、Claire Vallance、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0984

  日期：——

  The photolysis of the charge-transfer (CT) complex of benzofuran (3) and tetranitromethane in dichloromethane by light exciting only the CT complex (lambda>435 nm) gives the epimeric pairs of adducts, 3-nitro-2-trinitromethyl-2,3-dihydrobenzofurans 10 and 11, 2-nitro-3-trinitromethyl-2,3-dihydrobenzofurans 12 and 13, 3-hydroxy-2-trinitromethyl-2,3-dihydrobenzofurans 15 and 16, 7-nitro-4-trinitromethyl-4,7-dihydrobenzofurans 17 and 18, nitronic ester 14, dinitro dimers 19 and (21), 6-nitro- and 4-nitro-benzofurans 9 and 22, and 4-trinitromethylbenzofuran 21. In acetonitrile solution similar photolysis gives the same group of products and in addition the epimeric pairs, 2,3-dinitro-2,3-dihydrobenzofurans 4 and 5, 3-hydroxy-2-nitro-2,3-dihydrobenzofurans 6 and 7, and 3-nitrobenzofuran (8). Adducts 10, 11, 15 and 16 are formed by attack of trinitromethanide ion at C2 in the benzofuran radical cation 3(.+), adducts 12, 13 and 14 by similar attack al C3, and adducts 17 and 18, and 4-trinitromethylbenzofuran (21) by attack at C4.In 1,1,1,3,3,3-hexafluoropropan-2-ol the analogous photolysis of the CT complex of benzofuran (3) and tetranitromethane gives substantially the dinitro dimers 19 and 20, with small amounts of 3-nitro- (8), 6-nitro-(9), and 4-nitro-benzofuran (22).Reaction of benzofuran (3) with nitrogen dioxide in dichloromethane in the dark gives mainly the 2,3-dinitro adducts 4 and 5, and the 3-hydroxy-2-nitro adducts 6 and 7.High-level quantum chemical calculations (CASSCF/CASPT2), in combination with the valence bond configuration mixing (VBCM) model of the transition state of the radical cation-nucleophile reaction, were performed in order to obtain reactivity indices expressing the reactivity of the various sites of 3(.+) toward a nucleophile for comparison with the experimental results.X-ray crystal structures are reported for compounds 5, 8, 14 and 21.