(E)-3-[3-Hydroxy-2,2-dimethyl-8-(3-methyl-but-2-enyl)-chroman-6-yl]-acrylic acid methyl ester | 210979-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3-[3-Hydroxy-2,2-dimethyl-8-(3-methyl-but-2-enyl)-chroman-6-yl]-acrylic acid methyl ester
• CAS: 210979-37-6
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: OYHKFCIDCMXABV-VQHVLOKHSA-N

物化性质

• 沸点：
  475.936±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.104±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (E)-3-[3-Hydroxy-2,2-dimethyl-8-(3-methyl-but-2-enyl)-chroman-6-yl]-acrylic acid methyl ester 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以4.3 mg的产率得到(E)-3-[2,2-Dimethyl-8-(3-methyl-but-2-enyl)-3-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-chroman-6-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  Chemical Constituents of Brazilian Propolis and Their Cytotoxic Activities

  摘要：

  The EtOAc-soluble fraction of the MeOH extract of propolis afforded a new prenylated chromane derivative, 3-hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid (1), along with 22 known compounds, 2-23. Of the known compounds, 4, 7, 12-19, and 22 were isolated for the first time from propolis, and the absolute configuration of 23 was established as (2S,3R). Investigation suggested that Baccharis spp. are a significant source of tropical Brazilian propolis, in addition to Clusia minor, Clusia major, and Araucaria heterophylla. All the compounds were tested for their cytotoxicity toward human HT-1080 fibrosarcoma and murine colon 26-L5 carcinoma cells. Among these compounds, 9 and 19-21 showed potent cytotoxicity, having ED50 values equal to or less than 10 mu g/mL.

  DOI：

  10.1021/np980028c
• 作为产物：
  描述：

  重氮甲烷 、 (E)-3-(2,2-dimethyl-3,4-dihydro-3-hydroxy-8-prenyl-2H-1-benzopyran-6-yl)-2-propenoic acid 以 甲醇 为溶剂， 反应 12.0h， 以11.2 mg的产率得到(E)-3-[3-Hydroxy-2,2-dimethyl-8-(3-methyl-but-2-enyl)-chroman-6-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  Chemical Constituents of Brazilian Propolis and Their Cytotoxic Activities

  摘要：

  The EtOAc-soluble fraction of the MeOH extract of propolis afforded a new prenylated chromane derivative, 3-hydroxy-2,2-dimethyl-8-prenylchromane-6-propenoic acid (1), along with 22 known compounds, 2-23. Of the known compounds, 4, 7, 12-19, and 22 were isolated for the first time from propolis, and the absolute configuration of 23 was established as (2S,3R). Investigation suggested that Baccharis spp. are a significant source of tropical Brazilian propolis, in addition to Clusia minor, Clusia major, and Araucaria heterophylla. All the compounds were tested for their cytotoxicity toward human HT-1080 fibrosarcoma and murine colon 26-L5 carcinoma cells. Among these compounds, 9 and 19-21 showed potent cytotoxicity, having ED50 values equal to or less than 10 mu g/mL.

  DOI：

  10.1021/np980028c