(2R,3R)-2-chloro-3-hydroxy-1-phenyltetradecan-5-one | 1245039-48-8

• 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: (2R,3R)-2-chloro-3-hydroxy-1-phenyltetradecan-5-one
• CAS: 1245039-48-8
• 化学式: C₂₀H₃₁ClO₂
• 分子量: 338.918
• InChiKey: CFNPEXSGCVZXPC-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-十一酮 、 (R)-2-chlorohydrocinnamaldehyde 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， 反应 0.75h， 以63%的产率得到(2R,3S)-2-chloro-3-hydroxy-1-phenyltetradecan-5-one
  参考文献：
  名称：

  A Concise and Stereoselective Synthesis of Hydroxypyrrolidines: Rapid Synthesis of (+)-Preussin

  摘要：

  A convergent and stereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidines has been developed that involves reductive annulation of beta-Iminochlorohydrins, which are readily available from beta-ketochlorohydrins, and provides rapid access to a variety of 2,5-syn-pyrrolidines. Application of this process to the concise (three-step) synthesis of the fungal metabolite (+)-preussin and analogues of this substance is reported.

  DOI：

  10.1021/ol101631e

文献信息

• A Concise and Stereoselective Synthesis of Hydroxypyrrolidines: Rapid Synthesis of (+)-Preussin
  作者：Jason A. Draper、Robert Britton

  DOI：10.1021/ol101631e

  日期：2010.9.17

  A convergent and stereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidines has been developed that involves reductive annulation of beta-Iminochlorohydrins, which are readily available from beta-ketochlorohydrins, and provides rapid access to a variety of 2,5-syn-pyrrolidines. Application of this process to the concise (three-step) synthesis of the fungal metabolite (+)-preussin and analogues of this substance is reported.