5,7-dimethyl-4-(3,4-dimethoxyphenyl)-3,4-dihydrobenzopyran-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 5,7-dimethyl-4-(3,4-dimethoxyphenyl)-3,4-dihydrobenzopyran-2-one
• 英文别名: 4-(3,4-Dimethoxyphenyl)-5,7-dimethyl-3,4-dihydrochromen-2-one；4-(3,4-dimethoxyphenyl)-5,7-dimethyl-3,4-dihydrochromen-2-one
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: KLQFBVRHPGRVKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl (E)-3,4-dimethoxycinnamate 、 3,5-二甲基苯酚 在 三氟乙酸 作用下， 反应 24.0h， 以100%的产率得到5,7-dimethyl-4-(3,4-dimethoxyphenyl)-3,4-dihydrobenzopyran-2-one
  参考文献：
  名称：

  从苯酚和肉桂酸衍生物方便地合成二氢香豆素

  摘要：

  描述了合成二氢香豆素衍生物的简便方法。尽管发现在Pd（OAc）2存在下，苯酚与丙烯酸酯在三氟乙酸中反应生成香豆素的产物的收率很低，但在没有Pd（OAc）的情况下，二氢香豆素衍生物的收率高到高。 ）2当在该反应中使用带有给电子基团的肉桂酸乙酯时。

  DOI：

  10.1016/j.tet.2005.07.062

文献信息

• Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
  作者：Mayuri M. Naik、Durga P. Kamat、Santosh G. Tilve、Vijayendra P. Kamat

  DOI：10.1016/j.tet.2014.05.093

  日期：2014.8

  Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I-2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I-2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 degrees C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of Substituted (±)-3,4-Dihydrocoumarins Using H-Y Zeolite
  作者：Manojkumar R. Shukla、Prashant N. Patil、Prakash P. Wadgaonkar、Prafulla N. Josh、Manikrao M. Salunkhe

  DOI：10.1080/00397910008087290

  日期：2000.1

  Synthesis of substituted (+/-)-3,4 Dihydrocoumarins were prepared with the reaction between substituted cinnamic acid and phenol catalysed by eco-friendly solid-acid catalyst H-Y zeolite involving esterification followed by ring closure.
• Shukla; Padiya; Patil, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 372 - 375
  作者：Shukla、Padiya、Patil、Salunkhe

  DOI：——

  日期：——
• A convenient synthesis of dihydrocoumarins from phenols and cinnamic acid derivatives
  作者：Shinya Aoki、Chie Amamoto、Juzo Oyamada、Tsugio Kitamura

  DOI：10.1016/j.tet.2005.07.062

  日期：2005.9

  A facile procedure for synthesis of dihydrocoumarin derivatives was described. Although the yield of the products in the reaction of phenols with acrylates in trifluoroacetic acid in the presence of Pd(OAc)2 giving coumarins was found to be very low, dihydrocoumarin derivatives were obtained in good to high yields in the absence of Pd(OAc)2 when ethyl cinnamates bearing electron-donating groups were

  描述了合成二氢香豆素衍生物的简便方法。尽管发现在Pd（OAc）2存在下，苯酚与丙烯酸酯在三氟乙酸中反应生成香豆素的产物的收率很低，但在没有Pd（OAc）的情况下，二氢香豆素衍生物的收率高到高。 ）2当在该反应中使用带有给电子基团的肉桂酸乙酯时。