[1-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]phosphonic acid diethyl ester | 760998-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: [1-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]phosphonic acid diethyl ester
• 英文别名: 3,5-dimethyl-6-(1-diethylphosphonoethyl)-2-methoxy-4-pyrone；2-(1-Diethoxyphosphorylethyl)-6-methoxy-3,5-dimethylpyran-4-one
• CAS: 760998-23-0
• 化学式: C₁₄H₂₃O₆P
• 分子量: 318.307
• InChiKey: UUTWGPARTGSIHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1-(6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]phosphonic acid diethyl ester 在 四(三苯基膦)钯 氢氧化钾 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成
  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
• 作为产物：
  描述：

  4-甲基庚烷-3,5-二酮 在 lithium carbonate 、 sodium hydride 、 三乙胺 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 91.17h， 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：

  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

• A Scaffold-Tree-Merging Strategy for Prospective Bioactivity Annotation of γ-Pyrones
  作者：Stefan Wetzel、Wolfram Wilk、Samy Chammaa、Bianca Sperl、Anke G. Roth、Aybike Yektaoglu、Steffen Renner、Thorsten Berg、Christoph Arenz、Athanassios Giannis、Tudor I. Oprea、Daniel Rauh、Markus Kaiser、Herbert Waldmann

  DOI：10.1002/anie.200906555

  日期：2010.5.10

  target setting: The merging of natural product and non‐natural product based hierarchical scaffold trees annotated with bioactivity (see schematic illustration) together with brachiation along structural lines of biological relevance provides a novel strategy for the prospective identification of protein targets for compound collections inspired by natural product structures.

  战术目标设定：将天然产物和基于非天然产物的具有生物活性的分级支架树（参见示意图）与沿生物相关性结构分支的分支合并在一起，为前瞻性鉴定化合物靶标的蛋白质靶标提供了一种新颖的策略通过自然产品结构。
• Photochemical Relationships in Sacoglossan Polypropionates
  作者：Daniel R. Zuidema、Paul B. Jones

  DOI：10.1021/np049607+

  日期：2005.4.1

  photoisomerization with sunlight. Hydroperoxide, isolated form Placida dendritica, was synthesized both by singlet oxygenation of cyercene A using Rose Bengal and through the irradiation of cyercene A alone in aerobic solution. The observation that hydroperoxide could be made by singlet oxygenation of cyercene A and that this occurs when cyercene A alone is irradiated supported the hypothesis that gamma-pyrones

  合成了并茂A，并通过在阳光下的光致异构化将其转化为环戊烯A和异环庚烯A。氢过氧化物，是从Placida dendritica中分离出来的，它是通过使用玫瑰红（Bose Bengal）对cA进行单线氧化和通过在有氧溶液中单独照射cA来合成的。氢的过氧化物可以通过by A的单线态氧合而产生，并且仅在照射yer C时会发生这种现象，这支持了γ-吡喃酮可以充当三重态敏化剂的假设。这是通过使用并列烯A和模型γ-吡喃酮来敏化正丁基硫醚的光氧化作用而证实的。讨论了这些观察结果对Sacoglossan聚丙烯酸酯的生物合成意义。
• Biomimetic synthesis of (±)-9,10-deoxytridachione
  作者：John E. Moses、Robert M. Adlington、Raphaël Rodriguez、Serena J. Eade、Jack E. Baldwin

  DOI：10.1039/b418988d

  日期：——

  A tandem Suzuki-coupling/electrocyclisation reaction sequence was employed for the biomimetic synthesis of (+/-)-9,10-deoxytridachione.

  串联的铃木-偶联/电环化反应序列用于（+/-）-9,10-脱氧三丁酮的仿生合成。
• An efficient synthesis of cyercene A
  作者：John E. Moses、Jack E. Baldwin、Robert M. Adlington

  DOI：10.1016/j.tetlet.2004.06.125

  日期：2004.8

  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.
• Total synthesis of cyercene A and the biomimetic synthesis of (±)-9,10-deoxytridachione and (±)-ocellapyrone A
  作者：Raphaël Rodriguez、Robert M. Adlington、Serena J. Eade、Magnus W. Walter、Jack E. Baldwin、John E. Moses

  DOI：10.1016/j.tet.2007.03.057

  日期：2007.5

  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.