(2S,4R,6S)-2-[2-(4-Benzyloxy-phenyl)-ethyl]-4-bromo-6-(4-chloro-phenyl)-tetrahydro-pyran | 477284-04-1

• 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)-2-[2-(4-Benzyloxy-phenyl)-ethyl]-4-bromo-6-(4-chloro-phenyl)-tetrahydro-pyran
• 英文别名: (2S,4R,6S)-4-bromo-2-(4-chlorophenyl)-6-[2-(4-phenylmethoxyphenyl)ethyl]oxane
• CAS: 477284-04-1
• 化学式: C₂₆H₂₆BrClO₂
• 分子量: 485.848
• InChiKey: VLBVWPWOHOAHBS-RZFJZAQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4R,6S)-2-[2-(4-Benzyloxy-phenyl)-ethyl]-4-bromo-6-(4-chloro-phenyl)-tetrahydro-pyran 在 tris(dibenzylideneacetone)dipalladium (0) 、 偶氮二异丁腈 氢气 、 三正丁基氢锡 、 potassium carbonate 、 三氟乙酸 、 2-(二叔丁基膦)联苯 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 44.5h， 生成 Centrolobin
  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
• 作为产物：
  描述：

  (S)-1-(4-chlorophenyl)but-3-en-1-yl 3-(4-(benzyloxy)phenyl)propanoate 在 吡啶 、 4-二甲氨基吡啶 、 溴化锡 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,4R,6S)-2-[2-(4-Benzyloxy-phenyl)-ethyl]-4-bromo-6-(4-chloro-phenyl)-tetrahydro-pyran
  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

• 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.