(2S,4R,6S)-4-acetoxy-2-(3',4'-diacetoxyphenyl)-6-pentyltetrahydropyran | 473845-05-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2S,4R,6S)-4-acetoxy-2-(3',4'-diacetoxyphenyl)-6-pentyltetrahydropyran
• 英文别名: [(2S,4R,6S)-2-(3,4-diacetyloxyphenyl)-6-pentyloxan-4-yl] acetate
• CAS: 473845-05-5
• 化学式: C₂₂H₃₀O₇
• 分子量: 406.476
• InChiKey: XIDSIAZZUHSQOZ-ZVDOUQERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4R,6S)-4-acetoxy-2-(3',4'-diacetoxyphenyl)-6-pentyltetrahydropyran 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以68%的产率得到(2S,4R,6S)-2-(3',4'-hydroxyphenyl)-4-hydroxy-6-pentyltetrahydropyran
  参考文献：
  名称：

  Prins Cyclizations:  Labeling Studies and Application to Natural Product Synthesis

  摘要：

  [GRAPHICS]The first syntheses of two natural products, catechols 1 and 2, isolated from Plectranthus sylvestris (labiatae), are reported. Oxygen-18 labeling studies support the proposed intermediacy of a stabilized benzylic cation in the acid-promoted cyclization of an aldehyde and benzylic homoallylic alcohol possessing an electron-rich aromatic ring, In contrast, with an electron-deficient aromatic ring the pathway via a benzylic cation is only minor.

  DOI：

  10.1021/ol020127o
• 作为产物：
  描述：

  3,4-二乙酰氧基苯甲醛 在 三甲基硅乙酸酯 、 三氟化硼乙醚 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 6.17h， 生成 (2S,4R,6S)-4-acetoxy-2-(3',4'-diacetoxyphenyl)-6-pentyltetrahydropyran
  参考文献：
  名称：

  Prins Cyclizations:  Labeling Studies and Application to Natural Product Synthesis

  摘要：

  [GRAPHICS]The first syntheses of two natural products, catechols 1 and 2, isolated from Plectranthus sylvestris (labiatae), are reported. Oxygen-18 labeling studies support the proposed intermediacy of a stabilized benzylic cation in the acid-promoted cyclization of an aldehyde and benzylic homoallylic alcohol possessing an electron-rich aromatic ring, In contrast, with an electron-deficient aromatic ring the pathway via a benzylic cation is only minor.

  DOI：

  10.1021/ol020127o

文献信息

• Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans
  作者：Conor S. Barry、Nick Bushby、John R. Harding、Rachael A. Hughes、Gregory D. Parker、Richard Roe、Christine L. Willis

  DOI：10.1039/b504562b

  日期：——

  Trapping intermediates on the Prins cyclisation pathway with carbon-based nucleophiles has given further insight into factors affecting the acid-mediated reactions of homoallylic alcohols with aldehydes, enabling the design of efficient syntheses of 4-hydroxy-2,6-disubstituted tetrahydropyrans.

  用碳基亲核试剂在Prins环化途径上捕集中间体，可以进一步深入了解影响酸介导的均丙醇与醛反应的因素，从而可以设计出有效合成4-羟基-2,6-二取代四氢吡喃的化合物。