4-methoxy-3-benzoylcoumarin | 535921-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxy-3-benzoylcoumarin
• 英文别名: 3-benzoyl-4-methoxycoumarin；3-Benzoyl-4-methoxychromen-2-one
• CAS: 535921-01-8
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: XRGKMBRLLCYFDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-benzoylcoumarin 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-(benzylamino)-3-(hydroxy(phenyl)methyl)coumarin
  参考文献：
  名称：

  Conformation and photochemical properties of 3-benzoyl-4-benzylamino-7-dimethylaminocoumarin

  摘要：

  3-Benzoyl-4-benzylamino-7-dimethylaminocoumarin was synthesized and its conformation in solid state and solution was determined. While the X-ray crystal analysis showed an aromatic pi-pi stacking interaction in the solid state, the proton NMR studies suggested the presence of an intramolecular hydrogen bonding in solution. Adjacent functional group modifications through N-methylation, reduction of carbonyl group, or replacing the coumarin moiety to dimedone, all resulted in disrupting the pi-pi stacking conformation. Upon UV irradiation, the 7-methylamino group can be oxidized by molecular oxygen to the corresponding formamide in the absence of any external photosensitizers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.016
• 作为产物：
  描述：

  2H-1-苯并吡喃-2-酮,4-(苯甲酰氧基)- 在 potassium cyanide 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 4-methoxy-3-benzoylcoumarin
  参考文献：
  名称：

  从4-羟基香豆素高效合成三取代[1]苯并吡喃并[4,3 - b ]吡咯-4（1 H）-one衍生物

  摘要：

  从4-羟基香豆素合成了各种三取代的[1]苯并吡喃并[4,3 - b ]吡咯-4（1 H）-one衍生物，其六步产率为30–40％。合成的关键步骤是烯胺5的碱促进的分子内环化，然后脱水以生成稠合的吡咯环。

  DOI：

  10.1016/s0040-4039(03)00012-1

文献信息

• Efficient synthesis of trisubstituted [1]benzopyrano[4,3-b]pyrrol-4(1H)-one derivatives from 4-hydroxycoumarin
  作者：Yuan-Xiu Liao、Pei-Yu Kuo、Ding-Yah Yang

  DOI：10.1016/s0040-4039(03)00012-1

  日期：2003.2

  Various trisubstituted [1]benzopyrano[4,3-b]pyrrol-4(1H)-one derivatives have been synthesized from 4-hydroxycoumarin with a 30–40% yield over six steps. The key step of the synthesis is a base-promoted intramolecular cyclization of enamines 5, followed by dehydration to generate the fused pyrrole ring.

  从4-羟基香豆素合成了各种三取代的[1]苯并吡喃并[4,3 - b ]吡咯-4（1 H）-one衍生物，其六步产率为30–40％。合成的关键步骤是烯胺5的碱促进的分子内环化，然后脱水以生成稠合的吡咯环。
• Conformation and photochemical properties of 3-benzoyl-4-benzylamino-7-dimethylaminocoumarin
  作者：Chi-Hui Lin、Rong-Ren Chuang、Pei-Yu Kuo、Ding-Yah Yang

  DOI：10.1016/j.tetlet.2013.03.016

  日期：2013.5

  3-Benzoyl-4-benzylamino-7-dimethylaminocoumarin was synthesized and its conformation in solid state and solution was determined. While the X-ray crystal analysis showed an aromatic pi-pi stacking interaction in the solid state, the proton NMR studies suggested the presence of an intramolecular hydrogen bonding in solution. Adjacent functional group modifications through N-methylation, reduction of carbonyl group, or replacing the coumarin moiety to dimedone, all resulted in disrupting the pi-pi stacking conformation. Upon UV irradiation, the 7-methylamino group can be oxidized by molecular oxygen to the corresponding formamide in the absence of any external photosensitizers. (C) 2013 Elsevier Ltd. All rights reserved.