(+/-)-(5S,6R)-6-chloro-5-hydroxy-1,7-diphenylheptan-3-one

• 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: (+/-)-(5S,6R)-6-chloro-5-hydroxy-1,7-diphenylheptan-3-one
• 英文别名: 6-chloro-5-hydroxy-1,7-diphenylheptan-3-one；(5R,6S)-6-chloro-5-hydroxy-1,7-diphenylheptan-3-one
• 化学式: C₁₉H₂₁ClO₂
• 分子量: 316.828
• InChiKey: QFJLJQARZCIEAG-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(5S,6R)-6-chloro-5-hydroxy-1,7-diphenylheptan-3-one 、 甲胺 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 以53%的产率得到(+/-)-(2S,3S,5R)-2-benzyl-1-methyl-5-phenethylpyrrolidin-3-ol
  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
• 作为产物：
  描述：

  苄基丙酮 、 2-chloro-3-phenyl-propionaldehyde 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以75%的产率得到(+/-)-(5S,6R)-6-chloro-5-hydroxy-1,7-diphenylheptan-3-one
  参考文献：
  名称：

  Lithium Aldol Reactions of α-Chloroaldehydes Provide Versatile Building Blocks for Natural Product Synthesis

  摘要：

  α-氯醛的锂醇缩合反应提供了1,2-反式构型的β-酮氯醇。该反应的范围得到了展示，并介绍了其在合成haterumalide NA的C4-C15片段中的应用.

  DOI：

  10.1055/s-0030-1260032

文献信息

• Lithium Aldol Reactions of α-Chloroaldehydes Provide Versatile Building Blocks for Natural Product Synthesis
  作者：Robert Britton、Shira Halperin、Baldip Kang

  DOI：10.1055/s-0030-1260032

  日期：2011.6

  The lithium aldol reaction of α-chloroaldehydes provides 1,2-anti-configured β-ketochlorohydrins. The scope of this reaction is demonstrated as well as its application to the synthesis of the C4-C15 segment of haterumalide NA.

  α-氯醛的锂醇缩合反应提供了1,2-反式构型的β-酮氯醇。该反应的范围得到了展示，并介绍了其在合成haterumalide NA的C4-C15片段中的应用.
• 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.