(3S)-7-hydroxy-10-methoxy-9-propan-2-yloxy-3-propyl-3,4-dihydrobenzo[g]isochromen-1-one | 1394135-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (3S)-7-hydroxy-10-methoxy-9-propan-2-yloxy-3-propyl-3,4-dihydrobenzo[g]isochromen-1-one
• CAS: 1394135-76-2
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: PKQLQAIJZRVCEM-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-7-hydroxy-10-methoxy-9-propan-2-yloxy-3-propyl-3,4-dihydrobenzo[g]isochromen-1-one 在 C₃₈H₃₆N₂O₉V₂ 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以64%的产率得到
  参考文献：
  名称：

  Synthesis of 6,6′-Binaphthopyran-2-one Natural Products: Pigmentosin A, Talaroderxines A and B

  摘要：

  Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.

  DOI：

  10.1021/ol301743t
• 作为产物：
  描述：

  [(4S)-hept-1-en-4-yl] prop-2-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 正丁基锂 、 水 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 19.33h， 生成 (3S)-7-hydroxy-10-methoxy-9-propan-2-yloxy-3-propyl-3,4-dihydrobenzo[g]isochromen-1-one
  参考文献：
  名称：

  Synthesis of 6,6′-Binaphthopyran-2-one Natural Products: Pigmentosin A, Talaroderxines A and B

  摘要：

  Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.

  DOI：

  10.1021/ol301743t

文献信息

• Synthesis of 6,6′-Binaphthopyran-2-one Natural Products: Pigmentosin A, Talaroderxines A and B
  作者：Charles I. Grove、Michael J. Di Maso、Firoz A. Jaipuri、Michelle B. Kim、Jared T. Shaw

  DOI：10.1021/ol301743t

  日期：2012.9.7

  Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.