(3S)-3-[(2S,5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]butan-2-one | 1448011-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: (3S)-3-[(2S,5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]butan-2-one
• 英文别名: trans-nordavanone；(3S)-3-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]butan-2-one
• CAS: 1448011-60-6
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: RNEVZQGFNUZDJC-DVVUODLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl (2S)-2-[(2S,5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]propanoate 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (3S)-3-[(2S,5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]butan-2-one
  参考文献：
  名称：

  Synthesis of cis- and trans-Davanoids: Artemone, Hydroxydavanone, Isodavanone, and Nordavanone

  摘要：

  A concise and versatile synthesis of both cis and trans diastereomers of the natural products artemone, hydroxydavanone, isodavanone, and nordavanone has been accomplished. The preparation of trans-davanone is also described. Each synthesis is six to eight steps from geranyl acetate, with differentiation between cis and trans products occurring through a diastereoselective cyclization prior to derivatization. Many of these compounds are minor components of davana oil and have now been synthesized for the first time.

  DOI：

  10.1055/s-0033-1338429

文献信息

• One-Pot Tandem Aldol-Cycloetherification Protocol in the Enantioselective Synthesis of Davanoids
  作者：Vipin Kumar Singh、Jothi Lakshmi Nallasivam、Tushar Kanti Chakraborty

  DOI：10.1021/acs.joc.2c02865

  日期：2023.3.3

  Total synthesis of cis and trans diastereomers of prenylated davanoids like davanone, nordavanone, and davana acid ethyl ester was achieved in an enantioselective strategy. Various other davanoids could also be synthesized using standard procedures from the Weinreb amides derived from davana acids. Enantioselectivity in our synthesis was achieved employing a Crimmins’ non-Evans syn aldol reaction that

  顺反式全合成以对映选择性策略实现了异戊二烯化达瓦酮的非对映异构体，如达瓦酮、去甲达瓦酮和达瓦那酸乙酯。也可以使用源自大麻酸的 Weinreb 酰胺的标准程序合成各种其他大麻素类化合物。我们合成中的对映选择性是通过 Crimmins 的非 Evans syn 醛醇反应实现的，该反应固定了 C3-羟基的立体化学，而 C2-甲基在合成的后期差向异构化。路易斯酸介导的环醚化反应用于建立这些分子的四氢呋喃核心。有趣的是，Crimmins 的非 Evans syn aldol 协议的轻微改变导致 aldol 加合物完全转化为 davanoids 的核心四氢呋喃环，因此基本上将合成中的两个重要步骤相吻合。由此产生的一锅串联羟醛环醚化策略使对映选择性合成成为可能反式大麻酸乙酯和 2- epi -davanone/nordavanone 仅需三步即可获得出色的总收率。该方法的模块化将能够以立体化学纯形式合成
• Synthesis of cis- and trans-Davanoids: Artemone, Hydroxydavanone, Isodavanone, and Nordavanone
  作者：David Vosburg、Kanny Wan、Corwyn Evans-Klock、Brian Fielder

  DOI：10.1055/s-0033-1338429

  日期：——

  A concise and versatile synthesis of both cis and trans diastereomers of the natural products artemone, hydroxydavanone, isodavanone, and nordavanone has been accomplished. The preparation of trans-davanone is also described. Each synthesis is six to eight steps from geranyl acetate, with differentiation between cis and trans products occurring through a diastereoselective cyclization prior to derivatization. Many of these compounds are minor components of davana oil and have now been synthesized for the first time.