2-phenyl-6-((E)-styryl)tetrahydro-2H-pyran-4-ol

• 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: 2-phenyl-6-((E)-styryl)tetrahydro-2H-pyran-4-ol
• 英文别名: (E)-2-phenyl-6-styryl-tetrahydro-2H-pyran-4-ol；(2S,4R,6R)-2-phenyl-6-[(E)-2-phenylethenyl]oxan-4-ol
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: ONCPJVQNLOOYNM-ITEWYEAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-6-((E)-styryl)tetrahydro-2H-pyran-4-ol 在 palladium dichloride 偶氮二甲酸二异丙酯 、 氧气 、 potassium carbonate 、 三苯基膦 、 copper(l) chloride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 75.25h， 生成 1-phenyl-2-[(2R,4R,6S)-tetrahydro-4-hydroxy-6-phenyl-2H-pyran-2-yl]ethanone
  参考文献：
  名称：

  Total Synthesis of Diospongin A via an Enzymatic Kinetic Resolution of (±)-Tetrahydropyranol Derived from Prins Cyclization

  摘要：

  本文描述了一种简洁高效的二螺旋藻素 A 全合成方法；该方法以 Prins 环化和酶动力学解析为关键步骤。这是首次报道在脂肪酶介导下，通过普林斯环化衍生的(±)-四氢吡喃醇的酯交换反应合成二ospongin A。

  DOI：

  10.1055/s-2007-984886
• 作为产物：
  描述：

  1-苯基-3-丁烯-1-醇 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-phenyl-6-((E)-styryl)tetrahydro-2H-pyran-4-ol
  参考文献：
  名称：

  Total Synthesis of Diospongin A via an Enzymatic Kinetic Resolution of (±)-Tetrahydropyranol Derived from Prins Cyclization

  摘要：

  本文描述了一种简洁高效的二螺旋藻素 A 全合成方法；该方法以 Prins 环化和酶动力学解析为关键步骤。这是首次报道在脂肪酶介导下，通过普林斯环化衍生的(±)-四氢吡喃醇的酯交换反应合成二ospongin A。

  DOI：

  10.1055/s-2007-984886

文献信息

• Stereoselective synthesis of (−)-diospongins A and B and their stereoisomers at C-5
  作者：Nobuyuki Kawai、Sudhir Mahadeo Hande、Jun'ichi Uenishi

  DOI：10.1016/j.tet.2007.06.081

  日期：2007.9

  Antiosteoporotic diarylheptanoids (−)-diospongins A (1) and B (2) were synthesized stereoselectively. The key steps in the synthesis include a stereospecific PdII-catalyzed cyclization of chiral 1,5,7-trihydroxy-2-heptenes, 6a and 6b, to form cis and trans tetrahydropyran rings and a regioselective Wacker oxidation of β-(tetrahydro-2H-pyran-2-yl)styrenes, 5a and 5b. Their C-5 epimers 3 and 4 were also

  立体选择性地合成了抗骨质疏松症的二芳基庚烷类化合物（-）-双鞘脂A（1）和B（2）。合成的关键步骤包括手性1,5,7-三羟基-2-庚烯6a和6b的立体定向Pd II催化环化反应，形成顺式和反式四氢吡喃环，以及β-（四氢- 2 H-吡喃-2-基）苯乙烯5a和5b。还合成了它们的C-5差向异构体3和4。
• Montmorillonite clay catalyzed in situ Prins-type cyclisation reaction
  作者：J.S Yadav、B.V Subba Reddy、G Mahesh Kumar、Ch.V.S.R Murthy

  DOI：10.1016/s0040-4039(00)01891-8

  日期：2001.1

  Homoallylic alcohols smoothly undergo cross-coupling reactions with aldehydes on the surface of montmorillonite clay to generate 4-hydroxy-2,6-disubstituted tetrahydropyrans in high yields with high diastereoselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Iron-Catalyzed Synthesis of C2 Aryl- and <i>N</i>-Heteroaryl-Substituted Tetrahydropyrans
  作者：Cyril Bosset、Patrick Angibaud、Ian Stanfield、Lieven Meerpoel、Didier Berthelot、Amandine Guérinot、Janine Cossy

  DOI：10.1021/acs.joc.5b02371

  日期：2015.12.18

  An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.
• Total Synthesis of Diospongin A via an Enzymatic Kinetic Resolution of (±)-Tetrahydropyranol Derived from Prins Cyclization
  作者：J. Yadav、B. Padmavani、B. V. Reddy、Ch. Venugopal、A. Rao

  DOI：10.1055/s-2007-984886

  日期：——

  A concise and efficient total synthesis of diospongin A is described; it utilizes Prins cyclization and enzymatic kinetic re­solution as key steps. This is the first report on the synthesis of ­diospongin A by means of lipase-mediated transesterification of (±)-tetrahydropyranol derived from Prins cyclization.

  本文描述了一种简洁高效的二螺旋藻素 A 全合成方法；该方法以 Prins 环化和酶动力学解析为关键步骤。这是首次报道在脂肪酶介导下，通过普林斯环化衍生的(±)-四氢吡喃醇的酯交换反应合成二ospongin A。