2-(1-hydroxyeth-1-yl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one | 760998-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(1-hydroxyeth-1-yl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one
• 英文别名: 2-(1-Hydroxyethyl)-6-methoxy-3,5-dimethylpyran-4-one
• CAS: 760998-25-2
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: COBZJYJFGGPVOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-hydroxyeth-1-yl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [1-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]phosphonic acid diethyl ester
  参考文献：
  名称：

  An efficient synthesis of cyercene A

  摘要：

  An efficient approach to the total synthesis of the marine derived polypropionate cyercene A is described. A key feature of the synthesis is the development of methodology for the diastereoselective Wadsworth-Emmons type condensation of a functionalised gamma-pyrone unit. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.125
• 作为产物：
  描述：

  4-甲基庚烷-3,5-二酮 在 lithium carbonate 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 61.17h， 生成 2-(1-hydroxyeth-1-yl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one
  参考文献：
  名称：

  Total synthesis of cyercene A and the biomimetic synthesis of (±)-9,10-deoxytridachione and (±)-ocellapyrone A

  摘要：

  This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.03.057

文献信息

• Biomimetic Synthesis of Pyrone-Derived Natural Products: Exploring Chemical Pathways from a Unique Polyketide Precursor
  作者：Serena J. Eade、Magnus W. Walter、Colin Byrne、Barbara Odell、Raphaël Rodriguez、Jack E. Baldwin、Robert M. Adlington、John E. Moses

  DOI：10.1021/jo800220w

  日期：2008.7.1

  of diverse natural products with complex core structures such as 9,10-deoxytridachione, photodeoxytridachione and ocellapyrone A are derived in nature from a linear and conformationally strained all-(E) tetraene−pyrone precursor. We therefore synthesized such a precursor and investigated its biomimetic transformation under a variety of reaction conditions, both to the above natural products as well as

  我们的仿生假说提出，具有复杂核心结构的多种天然产物家族，例如9,10-脱氧三达酮，光脱氧三达酮和ocellapyrone A本质上是从线性和构象应变的全（E）四烯-吡喃酮前体衍生而来的。因此，我们合成了这种前体，并研究了其在多种反应条件下的仿生转化，转化为上述天然产物以及我们认为是“尚待发现”的天然产物的各种异构体。我们还在本文中报道了天然产物iso-9,10-脱氧三丁酮的首次合成。