rac-1-(5-hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano-[2,3-f ]chromen-6-yl)-2-methylbutan-1-one

• 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: rac-1-(5-hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano-[2,3-f ]chromen-6-yl)-2-methylbutan-1-one
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: CLJYXDMTPMCAQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 2-甲基-1-(2,4,6-三羟基苯基)丁烷-1-酮 在 ethylenediamine Tetraacetic Acid 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以85%的产率得到rac-1-(5-hydroxy-2,2,8,8-tetramethyl-2H,8H-pyrano-[2,3-f ]chromen-6-yl)-2-methylbutan-1-one
  参考文献：
  名称：

  Tricyclic Acylphloroglucinols from Hypericum lanceolatum and Regioselective Synthesis of Selancins A and B

  摘要：

  The chemical investigation of the chloroform extract of Hypericum lanceolatum guided by H-1 NMR, ESIMS, and TLC profiles led to the isolation of 11 new tricyclic acylphloroglucinol derivatives, named selancins A-I (1-9) and hyperselancins A and B (10 and 11), along with the known compound 3-O-geranylemodin (12), which is described for a Hypericum species for the first time. Compounds 8 and 9 are the first examples of natural products with a 6-aryl-2,2-dimethylchroman-4-one core fused with a dimethylpyran unit. The new compounds 1-9 are rare acylphloroglucinol derivatives with two fused dimethylpyran units. Compounds 10 and 11 are derivatives of polycyclic polyprenylated acylphloroglucinols related to hyperforin, the active component of St. John's wort. Their structures were elucidated by UV, IR, extensive 1D and 2D NMR experiments, HRESIMS, and comparison with the literature data. The absolute configurations of 5, 8, 10, and 11 were determined by comparing experimental and calculated electronic circular dichroism spectra. Compounds 1 and 2 were synthesized regioselectively in two steps. The cytotoxicity of the crude extract (88% growth inhibition at 50 mu g/mL) and of compounds 1-6, 8, 9, and 12 (no significant growth inhibition up to a concentration of 10 mM) against colon (HT-29) and prostate (PC-3) cancer cell lines was determined. No anthelmintic activity was observed for the crude extract.

  DOI：

  10.1021/acs.jnatprod.5b00673

文献信息

• Tricyclic Acylphloroglucinols from <i>Hypericum lanceolatum</i> and Regioselective Synthesis of Selancins A and B
  作者：Serge A. T. Fobofou、Katrin Franke、Andrea Porzel、Wolfgang Brandt、Ludger A. Wessjohann

  DOI：10.1021/acs.jnatprod.5b00673

  日期：2016.4.22

  The chemical investigation of the chloroform extract of Hypericum lanceolatum guided by H-1 NMR, ESIMS, and TLC profiles led to the isolation of 11 new tricyclic acylphloroglucinol derivatives, named selancins A-I (1-9) and hyperselancins A and B (10 and 11), along with the known compound 3-O-geranylemodin (12), which is described for a Hypericum species for the first time. Compounds 8 and 9 are the first examples of natural products with a 6-aryl-2,2-dimethylchroman-4-one core fused with a dimethylpyran unit. The new compounds 1-9 are rare acylphloroglucinol derivatives with two fused dimethylpyran units. Compounds 10 and 11 are derivatives of polycyclic polyprenylated acylphloroglucinols related to hyperforin, the active component of St. John's wort. Their structures were elucidated by UV, IR, extensive 1D and 2D NMR experiments, HRESIMS, and comparison with the literature data. The absolute configurations of 5, 8, 10, and 11 were determined by comparing experimental and calculated electronic circular dichroism spectra. Compounds 1 and 2 were synthesized regioselectively in two steps. The cytotoxicity of the crude extract (88% growth inhibition at 50 mu g/mL) and of compounds 1-6, 8, 9, and 12 (no significant growth inhibition up to a concentration of 10 mM) against colon (HT-29) and prostate (PC-3) cancer cell lines was determined. No anthelmintic activity was observed for the crude extract.