Benzenepropanol,a-[[(1S)-1-(4-chlorophenyl)-3-butenyl]oxy]-4-(phenylmethoxy)-, acetate | 477284-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzenepropanol,a-[[(1S)-1-(4-chlorophenyl)-3-butenyl]oxy]-4-(phenylmethoxy)-, acetate
• 英文别名: Acetic acid 3-(4-benzyloxy-phenyl)-1-[(S)-1-(4-chloro-phenyl)-but-3-enyloxy]-propyl ester
• CAS: 477284-13-2
• 化学式: C₂₈H₂₉ClO₄
• 分子量: 464.989
• InChiKey: RAEKGTVGXGCHEW-MBMZGMDYSA-N

物化性质

• 沸点：
  573.6±50.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Benzenepropanol,a-[[(1S)-1-(4-chlorophenyl)-3-butenyl]oxy]-4-(phenylmethoxy)-, acetate 在 溴化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到(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
• 作为产物：
  描述：

  4-氯苯甲醛 在 4-二甲氨基吡啶 吡啶 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 S-1,1'-联-2-萘酚 、 二异丁基氢化铝 、 N,N'-二环己基碳二亚胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 Benzenepropanol,a-[[(1S)-1-(4-chlorophenyl)-3-butenyl]oxy]-4-(phenylmethoxy)-, acetate
  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 and Structure Revision of Calyxin Natural Products
  作者：Xia Tian、James J. Jaber、Scott D. Rychnovsky

  DOI：10.1021/jo060094g

  日期：2006.4.1

  Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.