cis-6-(2-(4-hydroxyphenyl)-ethyl)-2-(4-hydroxyphenyl)-4-oxo-tetrahydropyran

• 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: cis-6-(2-(4-hydroxyphenyl)-ethyl)-2-(4-hydroxyphenyl)-4-oxo-tetrahydropyran
• 英文别名: (2S,6S)-2-[2-(4-hydroxyphenyl)ethyl]-6-(4-methoxyphenyl)oxan-4-one
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: RSGORVHQTBUQFE-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-6-(2-(4-hydroxyphenyl)-ethyl)-2-(4-hydroxyphenyl)-4-oxo-tetrahydropyran 在 三氟化硼乙醚 、 氢气 、 镍 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.33h， 生成 Centrolobin
  参考文献：
  名称：

  Exploiting the Maitland–Japp reaction: a synthesis of (±)-centrolobine

  摘要：

  Application of our one-pot, three-component variation of the Maitland-Japp reaction has led to the formation of a tetrahydropyran-4-one. which was converted in three steps to the antiparasitic and antibiotic natural product (+/-) centrolobine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.011
• 作为产物：
  描述：

  5-hydroxy-3-oxo-7-(4-tert-butyldimethylsilyloxyphenyl) heptanoic acid methyl ester 在 lithium hydroxide 、 双氧水 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 cis-6-(2-(4-hydroxyphenyl)-ethyl)-2-(4-hydroxyphenyl)-4-oxo-tetrahydropyran
  参考文献：
  名称：

  Exploiting the Maitland–Japp reaction: a synthesis of (±)-centrolobine

  摘要：

  Application of our one-pot, three-component variation of the Maitland-Japp reaction has led to the formation of a tetrahydropyran-4-one. which was converted in three steps to the antiparasitic and antibiotic natural product (+/-) centrolobine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.011

文献信息

• An Environmentally Benign Synthesis of <i>cis</i>-2,6-Disubstituted Tetrahydropyrans via Indium-Mediated Tandem Allylation/Prins Cyclization Reaction
  作者：Minh Pham、Amir Allatabakhsh、Thomas G. Minehan

  DOI：10.1021/jo7016857

  日期：2008.1.1

  cis-2,6-disubstituted tetrahydropyrans in good yields. Evidence suggests that InI, formed upon aldehyde (R1CHO) allylation in aqueous media, acts as a promoter for the silyl-Prins reaction with the second equivalent of added aldehyde (R2CHO). The preparation of cyclohexenyl-fused pyrans via this one-pot, three-component coupling process is presented, as is a short formal synthesis of (±)-centrolobine

  在铟金属的存在下，3-碘-2-[（（三甲基甲硅烷基）甲基]丙烯（1）与顺序添加的醛反应，以良好的产率提供顺式-2,6-二取代的四氢吡喃。有证据表明，在水性介质中醛（R 1 CHO）烯丙基化后形成的InI充当了甲硅烷基-Prins反应的促进剂，与第二当量添加的醛（R 2 CHO）发生了反应。提出了通过这种一锅，三组分偶联方法制备环己烯基稠合的吡喃的方法，这是（±）-中心洛宾的简短形式合成。
• An expedient synthesis of (±)-centrolobine
  作者：Paul A. Clarke、William H.C. Martin

  DOI：10.1016/j.tetlet.2004.10.035

  日期：2004.11

  An expedient synthesis of the antibiotic natural product centrolobine is reported, the key step being the one pot, multicomponent construction of a tetrahydropyran-4-one via a 'revisited' Maitland-Japp reaction. (C) 2004 Elsevier Ltd. All rights reserved.