4-hydroxy-6-non-1-enyl-tetrahydro-pyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-hydroxy-6-non-1-enyl-tetrahydro-pyran-2-one
• 英文别名: (4S,6S)-4-hydroxy-6-[(E)-non-1-enyl]oxan-2-one
• 化学式: C₁₄H₂₄O₃
• 分子量: 240.343
• InChiKey: CVYZIUWPNHGVMP-AYSSICMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  4-hydroxy-6-non-1-enyl-tetrahydro-pyran-2-one 在 4-二甲氨基吡啶 、 三乙胺 、 magnesium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 8-ethoxy-9-heptyl-13-hydroxy-tricyclo[6.5.1.0^2,6]tetradec-10-ene-3,14-dione
  参考文献：
  名称：

  Rapid Assembly of the Bicyclo[5.3.1]undecenone Core of Penostatin F:  A Successive Diels−Alder/Claisen Reaction Strategy with an Efficient Stereochemical Relay

  摘要：

  The first synthesis of the tricyclic core of Penostatin F (1) using a stereocontrolled Diels-Alder reaction and a Claisen rearrangement in succession has been achieved in nine steps from commercially available methyl acetoacetate and (E)-2-decenal. Penostatin F is a metabolite isolated from a fungal strain of Penicillium sp., OUPS-79, separated from the marine alga Enteromorphia intestinalis and exhibits significant cytotoxicity against cultured P388 Leukemia cells (ED50 = 1.4 mumol/mL).

  DOI：

  10.1021/ol049680r
• 作为产物：
  描述：

  反式-2-癸烯醛 在 tetramethylammonium borohydride 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 96.66h， 生成 4-hydroxy-6-non-1-enyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Rapid Assembly of the Bicyclo[5.3.1]undecenone Core of Penostatin F:  A Successive Diels−Alder/Claisen Reaction Strategy with an Efficient Stereochemical Relay

  摘要：

  The first synthesis of the tricyclic core of Penostatin F (1) using a stereocontrolled Diels-Alder reaction and a Claisen rearrangement in succession has been achieved in nine steps from commercially available methyl acetoacetate and (E)-2-decenal. Penostatin F is a metabolite isolated from a fungal strain of Penicillium sp., OUPS-79, separated from the marine alga Enteromorphia intestinalis and exhibits significant cytotoxicity against cultured P388 Leukemia cells (ED50 = 1.4 mumol/mL).

  DOI：

  10.1021/ol049680r

文献信息

• Rapid Assembly of the Bicyclo[5.3.1]undecenone Core of Penostatin F:  A Successive Diels−Alder/Claisen Reaction Strategy with an Efficient Stereochemical Relay
  作者：Louis Barriault、Patrick J. A. Ang、Roch M. A. Lavigne

  DOI：10.1021/ol049680r

  日期：2004.4.1

  The first synthesis of the tricyclic core of Penostatin F (1) using a stereocontrolled Diels-Alder reaction and a Claisen rearrangement in succession has been achieved in nine steps from commercially available methyl acetoacetate and (E)-2-decenal. Penostatin F is a metabolite isolated from a fungal strain of Penicillium sp., OUPS-79, separated from the marine alga Enteromorphia intestinalis and exhibits significant cytotoxicity against cultured P388 Leukemia cells (ED50 = 1.4 mumol/mL).