| 1003274-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• CAS: 1003274-32-5
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: LGOPWVJVVKHRQM-YWPYICTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  在 二苯甲醇 、 三甲基铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以61%的产率得到
  参考文献：
  名称：

  A Two-Directional Approach to a (−)-Dictyostatin C11−C23 Segment:  Development of a Highly Diastereoselective, Kinetically-Controlled Meerwein−Ponndorf−Verley Reduction

  摘要：

  A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.

  DOI：

  10.1021/ja077336u
• 作为产物：
  描述：

  在 吡啶 、 氢氟酸 作用下， 以 甲醇 为溶剂， 以1.51 g的产率得到
  参考文献：
  名称：

  A Two-Directional Approach to a (−)-Dictyostatin C11−C23 Segment:  Development of a Highly Diastereoselective, Kinetically-Controlled Meerwein−Ponndorf−Verley Reduction

  摘要：

  A three-step synthesis of a precursor to the C11-C23 segment of (-)-dictyostatin is described. The sequence features a sonication-assisted, enantioselective double hetero Diels-Alder (HDA) reaction catalyzed by Jacobsen's Cr(III) Schiff base catalyst, followed by a novel, highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of the hydropyranone subunits under kinetic control to yield the bis(axial alcohol) 4. Generalized studies of both the HDA and MPV methodologies are also described.

  DOI：

  10.1021/ja077336u

文献信息

• Diastereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyran-4-ones via Prins Cyclizations of Enecarbamates: A Formal Synthesis of (+)-Ratjadone A
  作者：Kimberly N. Cossey、Raymond L. Funk

  DOI：10.1021/ja046940r

  日期：2004.10.1

  precursors by alkylation of metalated (E)-enecarbamates with epoxides. The stereochemistry of the resultant trisubstituted (E)-enecarbamates is then transferred with high fidelity to afford the frequently observed and biologically significant all-cis-2,3,6-trisubstituted tetrahydropyran substructures of naturally occurring compounds. Other substituted tetrahydropyrans, including 2,3,5,6-tetrasubstituted

  烯氨基甲酸酯被证明是 Prins 环化的极好终止基团。这种方法的一个值得注意的特点是通过金属化 (E)-烯氨基甲酸酯与环氧化物的烷基化，可以轻松、立体选择性地构建环化前体。然后以高保真度转移所得三取代 (E)-烯氨基甲酸酯的立体化学，以提供经常观察到且具有生物学意义的天然化合物的全顺-2,3,6-三取代四氢吡喃亚结构。其他取代的四氢吡喃，包括 2,3,5,6-四取代、顺-2,3-二取代和顺-2,6-二取代，也可使用。这种方法促进了核输出抑制剂 (+)-ratjadone A 的异常简洁的正式全合成。