(5S,6R)-5-benzyloxy-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one | 955361-49-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 卡瓦内酯
• 英文名称: (5S,6R)-5-benzyloxy-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one
• 英文别名: (5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone；(2R,3S)-4-methoxy-2-(2-phenylethyl)-3-phenylmethoxy-2,3-dihydropyran-6-one
• CAS: 955361-49-6
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: MPEGCCDGOZRAQZ-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6R)-5-benzyloxy-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one 在 四氯化钛 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以89%的产率得到(+)-dihydrokawain-5-ol
  参考文献：
  名称：

  An efficient aldol-based approach for the synthesis of dihydrokawain-5-ol

  摘要：

  An efficient and simple aldol-based convergent approach toward the total synthesis of (+)- and (-)-dihydrokawain-5-ol is described. The key features of this synthetic strategy include Evans' aldol reaction and an ethyl acetate addition reaction for the formation of the six-membered ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.006
• 作为产物：
  描述：

  (2R,3R)-2-benzyloxy-3-(4-methoxybenzyloxy)-5-phenylpentan-1-ol 在 氯化锆(IV) 、 potassium carbonate 、 戴斯-马丁氧化剂 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 (5S,6R)-5-benzyloxy-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Enantioselective total synthesis of both the stereoisomers of dihydrokawain-5-ol

  摘要：

  The enantioselective synthesis of both the stereoisomers of dihydrokawain-5-ol is described. The key features of the synthetic strategy include (a) Sharpless asymmetric dihydroxylation, (b) Wittig olefination, and (c) formation of beta-keto ester to access the highly enantiomerically pure kavalactones. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2007.07.032

文献信息

• An efficient aldol-based approach for the synthesis of dihydrokawain-5-ol
  作者：Ahmed Kamal、Papagari Venkat Reddy、S. Prabhakar

  DOI：10.1016/j.tetasy.2009.08.006

  日期：2009.8

  An efficient and simple aldol-based convergent approach toward the total synthesis of (+)- and (-)-dihydrokawain-5-ol is described. The key features of this synthetic strategy include Evans' aldol reaction and an ethyl acetate addition reaction for the formation of the six-membered ring. (C) 2009 Elsevier Ltd. All rights reserved.
• Enantioselective total synthesis of both the stereoisomers of dihydrokawain-5-ol
  作者：Ahmed Kamal、Tadiparthi Krishnaji、P. Venkat Reddy

  DOI：10.1016/j.tetasy.2007.07.032

  日期：2007.8

  The enantioselective synthesis of both the stereoisomers of dihydrokawain-5-ol is described. The key features of the synthetic strategy include (a) Sharpless asymmetric dihydroxylation, (b) Wittig olefination, and (c) formation of beta-keto ester to access the highly enantiomerically pure kavalactones. (C) 2007 Published by Elsevier Ltd.