methyl (S)-1-(2,5-dimethoxyphenyl)-1H-benzo[f]chromene-3-carboxylate | 1131450-71-9

• 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: methyl (S)-1-(2,5-dimethoxyphenyl)-1H-benzo[f]chromene-3-carboxylate
• CAS: 1131450-71-9
• 化学式: C₂₃H₂₀O₅
• 分子量: 376.409
• InChiKey: UNFKTHOYZJQMCO-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl 4-(2,5-dimethoxyphenyl)-2-oxobut-3-enoate 、 2-萘酚 在 1-[3,5-双(三氟甲基)苯基]-3-[(1R,2R)-(-)-2-(二甲氨基)环己基]硫脲 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl (R)-1-(2,5-dimethoxyphenyl)-1H-benzo[f]chromene-3-carboxylate 、 methyl (S)-1-(2,5-dimethoxyphenyl)-1H-benzo[f]chromene-3-carboxylate
  参考文献：
  名称：

  Organocatalyzed Friedel–Craft-type reaction of 2-naphthol with β,γ-unsaturated α-keto ester to form novel optically active naphthopyran derivatives

  摘要：

  A novel bifunctional thiourea-tertiary-amine-catalyzed enantioselective Friedel-Craft-type addition reaction of 2-naphthol with beta,gamma-unsaturated alpha-keto ester was developed. Subsequent dehydration of the reaction adducts with a catalytic amount of concentrated H2SO4 in a one-pot fashion readily afforded a series of new optically active naphthopyran derivatives with moderate to good yields (up to 91%) and enantioselectivities (up to 90%). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.025

文献信息

• Organocatalyzed Friedel–Craft-type reaction of 2-naphthol with β,γ-unsaturated α-keto ester to form novel optically active naphthopyran derivatives
  作者：Xiao-Sheng Wang、Chang-Wu Zheng、Sheng-Li Zhao、Zhuo Chai、Gang Zhao、Gao-Sheng Yang

  DOI：10.1016/j.tetasy.2008.11.025

  日期：2008.12

  A novel bifunctional thiourea-tertiary-amine-catalyzed enantioselective Friedel-Craft-type addition reaction of 2-naphthol with beta,gamma-unsaturated alpha-keto ester was developed. Subsequent dehydration of the reaction adducts with a catalytic amount of concentrated H2SO4 in a one-pot fashion readily afforded a series of new optically active naphthopyran derivatives with moderate to good yields (up to 91%) and enantioselectivities (up to 90%). (C) 2008 Elsevier Ltd. All rights reserved.