(2S)-2-(but-3-en-1-yl)-6-hydroxy-2H-pyran-3(6H)-one | 1028777-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S)-2-(but-3-en-1-yl)-6-hydroxy-2H-pyran-3(6H)-one
• 英文别名: (2R,6S)-6-but-3-enyl-2-hydroxy-2H-pyran-5-one
• CAS: 1028777-35-6
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: UKIDJYWKJZKXGP-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-(but-3-en-1-yl)-6-hydroxy-2H-pyran-3(6H)-one 、 苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以50%的产率得到[(2S,6S)-6-but-3-enyl-5-oxo-2H-pyran-2-yl] benzoate
  参考文献：
  名称：

  A synthesis of the C1–C15 domain of the halichondrins

  摘要：

  A concise route to the C1-C15 domain of the halichondrins is described. The key reaction is the conversion of a furfuryl alcohol to a pyranone. The stereocenter of this pyranone serves as the starting point for the other eight stereocenters. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.018
• 作为产物：
  描述：

  (-)-5-hydroxy-5-(2-furyl)-1-pentene 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(2S)-2-(but-3-en-1-yl)-6-hydroxy-2H-pyran-3(6H)-one
  参考文献：
  名称：

  A synthesis of the C1–C15 domain of the halichondrins

  摘要：

  A concise route to the C1-C15 domain of the halichondrins is described. The key reaction is the conversion of a furfuryl alcohol to a pyranone. The stereocenter of this pyranone serves as the starting point for the other eight stereocenters. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.018

文献信息

• A new strategy for accessing (S)-1-(furan-2-yl)pent-4-en-1-ol: a key precursor of Ipomoeassin family of compounds and C1–C15 domain of halichondrins
  作者：Subba Rao Jammula、Venkateswara Rao Anna、Sudhakar Tatina、Thalishetti Krishna、B. Yogi Sreenivas、Manojit Pal

  DOI：10.1016/j.tetlet.2016.07.059

  日期：2016.8

  A highly efficient synthesis of (S)-1-(furan-2-yl)pent-4-en-1-ol, known to be an initial precursor of Ipomoeassin family of compounds and C1–C15 domain of halichondrins has been achieved via a sequence involving the use of Weinreb amide formation followed by Weinreb ketone synthesis and finally CBS (Corey–Bakshi–Shibata) reduction. Detailed study on improvement of each step is described. The title

  通过（S）-1-（呋喃-2-基）戊-4-烯-1-醇的高效合成，已知该化合物是Ipomoeassin家族化合物的第一先驱体，以及卤虫酮的C1-C15结构域该序列涉及使用Weinreb酰胺形成，然后进行Weinreb酮合成，最后还原CBS（Corey–Bakshi–Shibata）。描述了改进每个步骤的详细研究。标题化合物被转化为潜在的细胞毒性剂，用于进一步的药理研究。
• A synthesis of the C1–C15 domain of the halichondrins
  作者：Katrina L. Jackson、James A. Henderson、Jonathan C. Morris、Hajime Motoyoshi、Andrew J. Phillips

  DOI：10.1016/j.tetlet.2008.03.018

  日期：2008.4

  A concise route to the C1-C15 domain of the halichondrins is described. The key reaction is the conversion of a furfuryl alcohol to a pyranone. The stereocenter of this pyranone serves as the starting point for the other eight stereocenters. (c) 2008 Elsevier Ltd. All rights reserved.