2,4-dimethoxy-3'-nitro-benzophenone | 194290-68-1

• 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: 2,4-dimethoxy-3'-nitro-benzophenone
• 英文别名: 2,4-Dimethoxy-3'-nitro-benzophenon；(2,4-Dimethoxyphenyl)(3-nitrophenyl)methanone；(2,4-dimethoxyphenyl)-(3-nitrophenyl)methanone
• CAS: 194290-68-1
• 化学式: C₁₅H₁₃NO₅
• 分子量: 287.272
• InChiKey: FHMLVCBCYWMVHF-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  485.7±45.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  间硝基苯甲酰氯 、 间苯二甲醚 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 2,4-dimethoxy-3'-nitro-benzophenone
  参考文献：
  名称：

  Utility of Complementary Molecular Reactivity and Molecular Recognition (CMR/R) Technology and Polymer-Supported Reagents in the Solution-Phase Synthesis of Heterocyclic Carboxamides

  摘要：

  The use of our recently reported chemical library purification strategy in the development of a herbicidal lead, N-(3-benzoylphenyl)-3-(1,1-dimethylethyl)-1-methyl-1H-pyrazole-5-carboxamide (3), is described. The approach applying fundamental properties of complementary molecular reactivity and molecular recognition (CMR/R) as the basis for a general purification strategy was utilized. Polymeric reagents were used in the synthesis to generate reactive species involved in product formation, and complementary molecular reactivity/molecular recognition polymer 8 (CMR/R polymer 8) was used in the solution-phase syntheses of building blocks, primary libraries, and lead refinement libraries. An extension of the CMR/R methodology was applied, utilizing a sequestration enabling reagent (SER), transforming a reactant into an electrophilic species sequestrable by CMR/R polymer 8. This library purification strategy enabled rapid lead generation and lead refinement to afford herbicide 27o. The CMR/R solid-phase purification technique enabled a simple, general, and powerful protocol, eliminating the usual tedious and time-consuming methods required for solution-phase product purification. The result was the synthesis of hundreds of compounds, prepared in a relatively short time, leading to a compound with a 4-fold improvement in herbicidal activity over the initial lead.

  DOI：

  10.1021/jo970571i

文献信息

• Cyclobutene derivatives
  申请人：Sankyo Company Limited

  公开号：EP1070703A1

  公开（公告）日：2001-01-24

  Compounds of formula (I): in which: R1 and R2 each represents a variety of organic groups; R3 and R4 each represents hydrogen or a variety of organic groups; A represents a group of formula (A-1):    [in which: R5 represents hydrogen, hydroxy or alkyl, R6 represents hydroxy, alkoxy, alkylthio or an amine residue, X and Y each represents oxygen or sulphur, and Z represents a direct single bond between the nitrogen atom shown and the benzene ring shown in formula (I), or an alkylene group], G represents a single bond, alkylene or substituted alkylene; the broken line represents a single or double bond; when the broken line represents a double bond, D represents a carbon atom; and E represents an =N-O- group; when the broken line represents a single bond, D represents a CH group or a nitrogen atom, and E represents an oxygen atom, a sulphur atom, an -NH- group or a -CO- group}; and pharmaceutically acceptable salts, esters or other derivatives thereof have the ability to inhibit an ileal bile transporter and so may be used to treat or prevent hypercholesterolaemia.

  式(I)化合物： 其中R1 和 R2 各自代表各种有机基团；R3 和 R4 各自代表氢或各种有机基团；A 代表式（A-1）的基团： 其中R5代表氢、羟基或烷基，R6代表羟基、烷氧基、烷硫基或胺残基，X和Y各自代表氧或硫，Z代表式（I）所示的氮原子和苯环之间的直接单键或亚烷基]、 G 代表单键、亚烷基或取代亚烷基；断线代表单键或双键；当断线代表双键时，D 代表碳原子；E 代表 =N-O- 基团；当断线代表单键时，D代表CH基团或氮原子，E代表氧原子、硫原子、-NH-基团或-CO-基团}；其药学上可接受的盐、酯或其他衍生物具有抑制回肠胆汁转运体的能力，因此可用于治疗或预防高胆固醇血症。
• Utility of Complementary Molecular Reactivity and Molecular Recognition (CMR/R) Technology and Polymer-Supported Reagents in the Solution-Phase Synthesis of Heterocyclic Carboxamides
  作者：John J. Parlow、Deborah A. Mischke、Scott S. Woodard

  DOI：10.1021/jo970571i

  日期：1997.8.1

  The use of our recently reported chemical library purification strategy in the development of a herbicidal lead, N-(3-benzoylphenyl)-3-(1,1-dimethylethyl)-1-methyl-1H-pyrazole-5-carboxamide (3), is described. The approach applying fundamental properties of complementary molecular reactivity and molecular recognition (CMR/R) as the basis for a general purification strategy was utilized. Polymeric reagents were used in the synthesis to generate reactive species involved in product formation, and complementary molecular reactivity/molecular recognition polymer 8 (CMR/R polymer 8) was used in the solution-phase syntheses of building blocks, primary libraries, and lead refinement libraries. An extension of the CMR/R methodology was applied, utilizing a sequestration enabling reagent (SER), transforming a reactant into an electrophilic species sequestrable by CMR/R polymer 8. This library purification strategy enabled rapid lead generation and lead refinement to afford herbicide 27o. The CMR/R solid-phase purification technique enabled a simple, general, and powerful protocol, eliminating the usual tedious and time-consuming methods required for solution-phase product purification. The result was the synthesis of hundreds of compounds, prepared in a relatively short time, leading to a compound with a 4-fold improvement in herbicidal activity over the initial lead.
• Yamashita, Bulletin of the Chemical Society of Japan, 1928, vol. 3, p. 182
  作者：Yamashita

  DOI：——

  日期：——
• US6329405B1
  申请人：——

  公开号：US6329405B1

  公开（公告）日：2001-12-11
• 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.