(3S)-7-bromo-5,8-dimethoxy-3-methyl-3,4-dihydro-1H-isochromene | 1132702-02-3

• 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: (3S)-7-bromo-5,8-dimethoxy-3-methyl-3,4-dihydro-1H-isochromene
• CAS: 1132702-02-3
• 化学式: C₁₂H₁₅BrO₃
• 分子量: 287.153
• InChiKey: PMMQJUWZVVEYQK-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-7-bromo-5,8-dimethoxy-3-methyl-3,4-dihydro-1H-isochromene 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.42h， 以77%的产率得到(S)-(+)-7-bromo-3-methyl-3,4-dihydro-1H-2-benzopyran-5,8-dione
  参考文献：
  名称：

  Organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone

  摘要：

  A short and efficient organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone is achieved in a nine-step with 98.7% enantiomeric excess, by employing L-proline-catalyzed asymmetric of alpha-aminooxylation of aldehyde and Oxa-Pictet-Spengler cyclization as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.060
• 作为产物：
  描述：

  (S)-3-(4-bromo-2,5-dimethoxyphenyl)-2-propanol 、 氯甲基甲基醚 在 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以80%的产率得到(3S)-7-bromo-5,8-dimethoxy-3-methyl-3,4-dihydro-1H-isochromene
  参考文献：
  名称：

  Organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone

  摘要：

  A short and efficient organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone is achieved in a nine-step with 98.7% enantiomeric excess, by employing L-proline-catalyzed asymmetric of alpha-aminooxylation of aldehyde and Oxa-Pictet-Spengler cyclization as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.060

文献信息

• Organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone
  作者：Rajiv T. Sawant、Suresh B. Waghmode

  DOI：10.1016/j.tet.2008.12.060

  日期：2009.2

  A short and efficient organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone is achieved in a nine-step with 98.7% enantiomeric excess, by employing L-proline-catalyzed asymmetric of alpha-aminooxylation of aldehyde and Oxa-Pictet-Spengler cyclization as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.