2-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetaldehyde | 462094-43-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetaldehyde
• 英文别名: 2-(3,4-Dimethyl-2-oxochromen-7-yl)oxyacetaldehyde
• CAS: 462094-43-5
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: MLCKLRLJXHJMAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  2-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetaldehyde 在 甲基磺酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 3,4-Dimethylgeiparvarin
  参考文献：
  名称：

  Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. synthesis and SAR studies

  摘要：

  Natural geiparvarin 1 and a number of its analogues were prepared and tested as inhibitors of both monoamine oxidase isoforms, MAO-B and MAO-A. The desmethyl congener 6 of geiparvarin, proved potent and selective MAO-B inhibitor (PIC50 = 7.55 vs 4.62). X-ray crystallography and molecular modelling studies helped the understanding of the observed structure-activity relationships. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00798-9
• 作为产物：
  描述：

  二甲基伞形酮 在 Pd-BaSO₄ sodium hydroxide 、 氯化亚砜 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 水 、 丙酮 、 甲苯 为溶剂， 反应 13.0h， 生成 2-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]acetaldehyde
  参考文献：
  名称：

  2-氧代乙氧基香豆素的新便捷途径：天然产物合成中的关键中间体

  摘要：

  提出了一种从羟基香豆素开始合成香豆素氧基醛的新方法。这些化合物是制备天然产物（如geiparvarin和补骨脂素）中有用的中间体，现在可以通过简单的后处理程序以高收率获得。此外，所报道的途径已经应用于二羟基香豆素。

  DOI：

  10.1016/s0040-4020(02)00442-8

文献信息

• A convenient synthesis of psoralens
  作者：Stefano Chimichi、Marco Boccalini、Barbara Cosimelli、Giampietro Viola、Daniela Vedaldi、Francesco Dall'Acqua

  DOI：10.1016/s0040-4020(02)00441-6

  日期：2002.6

  An efficient synthesis (yields >70%) of linear 7H-furo[3,2-g]chromen-7-one derivatives (psoralens or furocoumarins) has been carried out starting from ring-substituted 2-(coumarin-7-yl)oxyaldehydes; moreover, the phototoxicity of these compounds has been tested on a cultured cell line of murine fibroblast.

  从环取代的2-（香豆素-7-基）开始，已经进行了线性7 H-呋喃[3,2 - g ] chromen-7-one衍生物（补骨脂素或呋喃香豆素）的有效合成（收率> 70％）。）乙醛; 此外，已经在鼠成纤维细胞的培养细胞系上测试了这些化合物的光毒性。
• A new convenient route to 2-oxoethoxycoumarins: key intermediates in the synthesis of natural products
  作者：Stefano Chimichi、Marco Boccalini、Barbara Cosimelli

  DOI：10.1016/s0040-4020(02)00442-8

  日期：2002.6

  A new synthetic route to coumarinyloxyaldehydes starting from hydroxycoumarins is presented; these compounds, useful intermediates in the preparation of natural products such as geiparvarin and psoralens, are now available in excellent yields with a simple workup procedure. Moreover the reported route has been applied to dihydroxycoumarins.

  提出了一种从羟基香豆素开始合成香豆素氧基醛的新方法。这些化合物是制备天然产物（如geiparvarin和补骨脂素）中有用的中间体，现在可以通过简单的后处理程序以高收率获得。此外，所报道的途径已经应用于二羟基香豆素。
• Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. synthesis and SAR studies
  作者：Angelo Carotti、Antonio Carrieri、Stefano Chimichi、Marco Boccalini、Barbara Cosimelli、Carmela Gnerre、Andrea Carotti、Pierre-Alain Carrupt、Bernard Testa

  DOI：10.1016/s0960-894x(02)00798-9

  日期：2002.12

  Natural geiparvarin 1 and a number of its analogues were prepared and tested as inhibitors of both monoamine oxidase isoforms, MAO-B and MAO-A. The desmethyl congener 6 of geiparvarin, proved potent and selective MAO-B inhibitor (PIC50 = 7.55 vs 4.62). X-ray crystallography and molecular modelling studies helped the understanding of the observed structure-activity relationships. (C) 2002 Elsevier Science Ltd. All rights reserved.