4-[tert-butyl(dimethyl)silyl]oxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-ol | 676124-29-1

• 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: 4-[tert-butyl(dimethyl)silyl]oxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-ol
• CAS: 676124-29-1
• 化学式: C₁₇H₂₈O₅Si
• 分子量: 340.492
• InChiKey: SWNBZDQPAMGMBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  419.3±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[tert-butyl(dimethyl)silyl]oxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-ol 在 potassium tert-butylate 作用下， 以 乙腈 为溶剂， 反应 0.7h， 生成 ethyl 2-[(3R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-yl]acetate
  参考文献：
  名称：

  Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones

  摘要：

  The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig-oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 mug/mL, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.015
• 作为产物：
  描述：

  ethyl (2-acetoxymethyl-3,4-dimethoxyphenyl)glyoxylate 在 咪唑 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.17h， 生成 4-[tert-butyl(dimethyl)silyl]oxy-7,8-dimethoxy-3,4-dihydro-1H-isochromen-3-ol
  参考文献：
  名称：

  Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones

  摘要：

  The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig-oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 mug/mL, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.015

文献信息

• Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones
  作者：Darı́o A. Bianchi、Emma G. Sutich、Teodoro S. Kaufman

  DOI：10.1016/j.bmcl.2003.11.015

  日期：2004.2

  The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig-oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 mug/mL, respectively. (C) 2003 Elsevier Ltd. All rights reserved.