(3R)-7-hydroxy-10-methoxy-3-methyl-9-propan-2-yloxy-3,4-dihydrobenzo[g]isochromen-1-one | 1305340-26-4

• 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: (3R)-7-hydroxy-10-methoxy-3-methyl-9-propan-2-yloxy-3,4-dihydrobenzo[g]isochromen-1-one
• CAS: 1305340-26-4
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: IBNJYQXJZUNXHO-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  (3R)-7-hydroxy-10-methoxy-3-methyl-9-propan-2-yloxy-3,4-dihydrobenzo[g]isochromen-1-one 在 C₃₈H₃₆N₂O₉V₂ 、 氧气 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 31.0h， 生成
  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：

  在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.75h， 以74%的产率得到(3R)-7-hydroxy-10-methoxy-3-methyl-9-propan-2-yloxy-3,4-dihydrobenzo[g]isochromen-1-one
  参考文献：
  名称：

  (-)-Viriditoxin 的合成：靶向细菌细胞分裂蛋白 FtsZ 的 6,6'-Binaphthopyran-2-one

  摘要：

  远程控制：钒催化剂是合成抗菌天然产物绿色毒素的关键。非手性催化剂表现出适度水平的由内酯立体中心诱导的远程非对映控制，手性催化剂可用于增强或逆转这种固有的选择性。

  DOI：

  10.1002/anie.201007298

文献信息

• Synthesis of (−)-Viriditoxin: A 6,6′-Binaphthopyran-2-one that Targets the Bacterial Cell Division Protein FtsZ
  作者：Young Sam Park、Charles I. Grove、Marcos González-López、Sameer Urgaonkar、James C. Fettinger、Jared T. Shaw

  DOI：10.1002/anie.201007298

  日期：2011.4.11

  Remote control: Vanadium catalysts provide the key to synthesizing the bacteria‐fighting natural product viriditoxin. An achiral catalyst shows modest levels of remote diastereocontrol induced by the lactone stereogenic center and chiral catalysts can be used to enhance or reverse this inherent selectivity.

  远程控制：钒催化剂是合成抗菌天然产物绿色毒素的关键。非手性催化剂表现出适度水平的由内酯立体中心诱导的远程非对映控制，手性催化剂可用于增强或逆转这种固有的选择性。
• 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.