2-hydroxy-4-methoxy-3'-nitrobenzophenone | 126077-53-0

• 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: 2-hydroxy-4-methoxy-3'-nitrobenzophenone
• 英文别名: (2-Hydroxy-4-methoxyphenyl)(3-nitrophenyl)methanone；(2-hydroxy-4-methoxyphenyl)-(3-nitrophenyl)methanone
• CAS: 126077-53-0
• 化学式: C₁₄H₁₁NO₅
• 分子量: 273.245
• InChiKey: WYQAXZJRENCXQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-dimethoxy-3'-nitro-benzophenone 在 盐酸 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 以5.95 g的产率得到2-hydroxy-4-methoxy-3'-nitrobenzophenone
  参考文献：
  名称：

  Facile synthesis, spectroscopic characterization and X-ray analysis of 4-alkoxylated 2-hydroxybenzophenones

  摘要：

  Two 2-hydroxy-4-alkoxy-3'-nitrobenzophenones were synthesized in a facile way. Their structures were characterized with the aid of mass spectra and H-1 NMR spectra analysis, as well as X-ray diffraction analysis. The H-1 NMR spectra showed an intramolecular hydrogen bond formation in their structures. Compound 1 crystallizes in the monoclinic P2 (1) space group with the crystal cell parameters a = 3.9318(4) angstrom, b = 7.1042(9) angstrom, c = 22.0400(19) angstrom, alpha = 90.00 degrees, beta = 92.3140(10)degrees, gamma = 90.00 degrees, V = 615.13(11) angstrom(3) and Z = 2. Compound 2 crystallizes in the monoclinic space group P2 (1)/n with the crystal cell parameters a = 3.9765(5) angstrom, b = 11.8286(15) angstrom, c = 28.867(3) angstrom, alpha = 90.00 degrees beta = 92.8710(10)degrees, gamma = 90.00 degrees, V = 1356.1(3) angstrom(3) and Z = 4. Results showed that the benzophenone skeletons are non-planar, with a large torsion to minimize their repulsive force. The substituted nitro or alkoxy groups are essentially coplanar with respect to the benzene rings to which it connected, whereas the carbonyl group in benzophenone skeleton is coplanar with the benzene ring which is substituted by alkoxy group. Classic and non-classic intra- and intermolecular hydrogen bonds, together with the pi-pi stacking interactions stabilize their molecular conformations. The minor variations in the alkoxy group substituent cause great difference in their intermolecular hydrogen bond formation and stacking mode. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.11.033

文献信息

• US4902787A
  申请人：——

  公开号：US4902787A

  公开（公告）日：1990-02-20
• Facile synthesis, spectroscopic characterization and X-ray analysis of 4-alkoxylated 2-hydroxybenzophenones
  作者：Lihua Lu、Liang He

  DOI：10.1016/j.molstruc.2011.11.033

  日期：2012.2

  Two 2-hydroxy-4-alkoxy-3'-nitrobenzophenones were synthesized in a facile way. Their structures were characterized with the aid of mass spectra and H-1 NMR spectra analysis, as well as X-ray diffraction analysis. The H-1 NMR spectra showed an intramolecular hydrogen bond formation in their structures. Compound 1 crystallizes in the monoclinic P2 (1) space group with the crystal cell parameters a = 3.9318(4) angstrom, b = 7.1042(9) angstrom, c = 22.0400(19) angstrom, alpha = 90.00 degrees, beta = 92.3140(10)degrees, gamma = 90.00 degrees, V = 615.13(11) angstrom(3) and Z = 2. Compound 2 crystallizes in the monoclinic space group P2 (1)/n with the crystal cell parameters a = 3.9765(5) angstrom, b = 11.8286(15) angstrom, c = 28.867(3) angstrom, alpha = 90.00 degrees beta = 92.8710(10)degrees, gamma = 90.00 degrees, V = 1356.1(3) angstrom(3) and Z = 4. Results showed that the benzophenone skeletons are non-planar, with a large torsion to minimize their repulsive force. The substituted nitro or alkoxy groups are essentially coplanar with respect to the benzene rings to which it connected, whereas the carbonyl group in benzophenone skeleton is coplanar with the benzene ring which is substituted by alkoxy group. Classic and non-classic intra- and intermolecular hydrogen bonds, together with the pi-pi stacking interactions stabilize their molecular conformations. The minor variations in the alkoxy group substituent cause great difference in their intermolecular hydrogen bond formation and stacking mode. (C) 2011 Elsevier B.V. All rights reserved.