(2S,4R,6S)-6-[2-[4-(benzyloxy)phenyl]ethyl]-4-bromo-2-[4-(methoxy)phenyl]tetrahydropyran | 477284-03-0

• 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)-6-[2-[4-(benzyloxy)phenyl]ethyl]-4-bromo-2-[4-(methoxy)phenyl]tetrahydropyran
• 英文别名: (2S,4R,6S)-2-(4-(benzyloxy)phenethyl)-4-bromo-tetrahydro-6-(4-methoxyphenyl)-2H-pyran；(2S,4R,6S)-4-bromo-2-(4-methoxyphenyl)-6-[2-(4-phenylmethoxyphenyl)ethyl]oxane
• CAS: 477284-03-0
• 化学式: C₂₇H₂₉BrO₃
• 分子量: 481.429
• InChiKey: RPSDVKIUCOEHBJ-NPAAKHOSSA-N

物化性质

• 沸点：
  591.4±50.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R,6S)-6-[2-[4-(benzyloxy)phenyl]ethyl]-4-bromo-2-[4-(methoxy)phenyl]tetrahydropyran 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 苯 为溶剂， 反应 16.0h， 以98%的产率得到(2S,6R)-2-(4-(benzyloxy)phenethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Prins Cyclizations in Silyl Additives with Suppression of Epimerization:  Versatile Tool in the Synthesis of the Tetrahydropyran Backbone of Natural Products

  摘要：

  A catalytic Prins cyclization reaction has been developed. The involvement of trimethylsilyl halides offers a versatile route to the formation of cis4-halo-2,6-disubstituted tetrahydropyran rings. The problem of epimerization in Prins cyclization has also been addressed in the total synthesis of (-)-centrolobine using this methodology.

  DOI：

  10.1021/ol051951q
• 作为产物：
  描述：

  3-[4-(苄氧基)苯基]丙酸 在 4-二甲氨基吡啶 吡啶 、 4-二甲氨基吡啶 、 溴化锡 、 二异丁基氢化铝 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 28.3h， 生成 (2S,4R,6S)-6-[2-[4-(benzyloxy)phenyl]ethyl]-4-bromo-2-[4-(methoxy)phenyl]tetrahydropyran
  参考文献：
  名称：

  Synthesis of (−)-Centrolobine by Prins Cyclizations that Avoid Racemization

  摘要：

  [GRAPHICS]The segment-coupling Prins cyclization avoids two of the problems common to other Prins cyclization protocols: side-chain exchange and partial racemization by reversible 2-oxonia Cope rearrangement. Model studies demonstrate the stereochemical fidelity of Prins cyclizations using alpha-acetoxy ethers compared with direct aldehyde-alcohol Prins reactions. Furthermore, we propose a mechanism for the racemization observed in some intermolecular Prins cyclizations. Two straightforward syntheses of optically pure (-)-centrolobine highlight the utility of Prins cyclizations.

  DOI：

  10.1021/ol026751i

文献信息

• Prins Cyclizations in Silyl Additives with Suppression of Epimerization:  Versatile Tool in the Synthesis of the Tetrahydropyran Backbone of Natural Products
  作者：Kok-Ping Chan、Teck-Peng Loh

  DOI：10.1021/ol051951q

  日期：2005.9.1

  A catalytic Prins cyclization reaction has been developed. The involvement of trimethylsilyl halides offers a versatile route to the formation of cis4-halo-2,6-disubstituted tetrahydropyran rings. The problem of epimerization in Prins cyclization has also been addressed in the total synthesis of (-)-centrolobine using this methodology.
• Synthesis of (−)-Centrolobine by Prins Cyclizations that Avoid Racemization
  作者：Shinji Marumoto、James J. Jaber、Justin P. Vitale、Scott D. Rychnovsky

  DOI：10.1021/ol026751i

  日期：2002.10.1

  [GRAPHICS]The segment-coupling Prins cyclization avoids two of the problems common to other Prins cyclization protocols: side-chain exchange and partial racemization by reversible 2-oxonia Cope rearrangement. Model studies demonstrate the stereochemical fidelity of Prins cyclizations using alpha-acetoxy ethers compared with direct aldehyde-alcohol Prins reactions. Furthermore, we propose a mechanism for the racemization observed in some intermolecular Prins cyclizations. Two straightforward syntheses of optically pure (-)-centrolobine highlight the utility of Prins cyclizations.