7-乙氧基-4,8-二甲基-2H-苯并吡喃-2-酮 | 312288-25-8

• 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
• 中文名称: 7-乙氧基-4,8-二甲基-2H-苯并吡喃-2-酮
• 英文名称: 7-ethoxy-4,8-dimethyl-2H-chromen-2-one
• 英文别名: 7-ethoxy-4,8-dimethylchromen-2-one
• CAS: 312288-25-8
• 化学式: C₁₃H₁₄O₃
• mdl: MFCD01107160
• 分子量: 218.252
• InChiKey: OUVIJCNGGNDYHX-UHFFFAOYSA-N

物化性质

• 沸点：
  357.3±42.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-乙氧基-4,8-二甲基-2H-苯并吡喃-2-酮 、 二氟甲烷亚磺酸钠 在 溶剂红 43 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以53%的产率得到3-difluoromethyl-7-ethoxy-4,8-dimethyl-2H-chromen-2-one
  参考文献：
  名称：

  Visible-Light- and Oxygen-Promoted Direct Csp²-H Radical Difluoromethylation of Coumarins and Antifungal Activities

  摘要：

  An efficient general method using a clean and transition-metal-free photochemical strategy for the direct Csp(2)-H radical difluoromethylation of coumarins with HCF2SO2Na was developed. The visible-light-promoted strategy proceeds with 5 mol % Eosin Y under mild reaction conditions and showed excellent functional group compatibility. The control experiments illustrated that O(2)(center dot- )participated in this process and plays an important role in the reactions. Moreover, the representative products exhibited excellent antifungal activities in vitro. It was noted that the EC50 value of compound 3a was determined to be as low as 1.5463 mu g/mL against Rhizoctorzia solani, which was better than Boscalid (EC50 = 2.9767 mu g/mL).

  DOI：

  10.1021/acs.orglett.8b02965
• 作为产物：
  描述：

  一氧化碳 、 3-ethoxy-2-methyl-6-(prop-1-en-2-yl)phenol 在 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 copper(II) acetate monohydrate 、 silver carbonate 作用下， 以 邻二甲苯 为溶剂， 反应 17.0h， 以55%的产率得到7-乙氧基-4,8-二甲基-2H-苯并吡喃-2-酮
  参考文献：
  名称：

  Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives

  摘要：

  Cp*Co(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C-H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.

  DOI：

  10.1021/acs.orglett.5b02728

文献信息

• INHIBITORS OF PLASMODIUM FALCIPARUM EQUILIBRATIVE NUCLEOSIDE TRANSPORTER TYPE I AS ANTI-PARASITIC COMPOUNDS
  申请人：TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20160122362A1

  公开（公告）日：2016-05-05

  Inhibitors of Plasmodium falciparum equilibrative nucleoside transporter type 1 are identified and methods of use as anti-parasitic compounds are provided.
• US5216176A
  申请人：——

  公开号：US5216176A

  公开（公告）日：1993-06-01
• US9695193B2
  申请人：——

  公开号：US9695193B2

  公开（公告）日：2017-07-04
• [EN] 7-ALKOXYCOUMARINS, DIHYDROPSORALENS, AND BENZODIPYRANONES AS PHOTO-ACTIVATED THERAPEUTIC AGENTS AND INHIBITORS OF EPIDERMAL GROWTH FACTOR
  申请人：——

  公开号：WO1990008529A2

  公开（公告）日：1990-08-09

  [EN] A photochemotherapeutic compound of formula (I), wherein (i) n is zero, W is a (C1-16) alkyl, alkenyl, or alkynyl linear or branched chain hydrocarbon, having no more than four O, N, or S atoms in or attached to the chain; or (ii) n is 1, W is CR2, and R, R', and R'' are independently H or CH3; or (iii) n is 2, W is CR2, and R, R', and R'' are independently H or CH3; and A, B, C, and D are independently selected from hydrogen, alkyl, aryl, halogen, amino, aminoalkyl, nitro, alkoxy, aryloxy, hydroxy, carboxy, haloalkyl, or haloalkoxy.
  [FR] L'invention concerne un composé photochimiothérapeutique de formule (I), dans laquelle soit (i) représente zéro, W représente un hydrocarbure à chaîne linéaire ou ramifiée d'alcoyle (C1-16), alkényle ou alkynyle, ne comportant pas plus de quatre atomes de O, N ou S dans la chaîne ou fixés à la chaîne; ou (ii) n représente 1, W représente CR2, et R, R', et R'' représentent indépendamment H ou CH3; ou (iii) n représente 2, W représente CR2, et R, R', et R'' représentent indépendamment H ou CH3; et A, B, C et D sont choisis indépendamment parmi, hydrogène, alcoyle, aryle, halogène, amino, aminoalcoyle, nitro, alkoxy, aryloxy, hydroxy, carboxy, haloacoyle ou haloalkoxy.
• [EN] INHIBITORS OF PLASMODIUM FALCIPARUM EQUILIBRATIVE NUCLEOSIDE TRANSPORTER TYPE 1 AS ANTI-PARASITIC COMPOUNDS<br/>[FR] INHIBITEURS DU TRANSPORTEUR DE NUCLÉOSIDES ÉQUILIBRANT DE TYPE 1 DE PLASMODIUM FALCIPARUM EN TANT QUE COMPOSÉS ANTI-PARASITAIRES
  申请人：UNIV COLUMBIA

  公开号：WO2014210319A2

  公开（公告）日：2014-12-31

  Inhibitors of Plasmodium falciparum equilibrative nucleoside transporter type 1 are identified and methods of use as anti-parasitic compounds are provided.