2-ethyl-4-methoxy-3,5-dimethyl-2H-pyran-2-one | 130858-62-7

• 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-ethyl-4-methoxy-3,5-dimethyl-2H-pyran-2-one
• 英文别名: 6-ethyl-4-methoxy-3,5-dimethyl-2H-pyran-2-one；6-Ethyl-4-methoxy-3,5-dimethylpyran-2-one
• CAS: 130858-62-7
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: NNVHQEZTJFOKQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-4-methoxy-3,5-dimethyl-2H-pyran-2-one 在 吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 praseodymium(III) chloride 、 草酰氯 、 对甲苯磺酸 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 酒石酸 、 三乙胺 、 cesium fluoride 、 三氟乙酸酐 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 6.0h， 生成 6-((4R,5S)-5-Acetyl-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-4-methoxy-3,5-dimethyl-pyran-2-one
  参考文献：
  名称：

  Total synthesis of (+)-verrucosidin

  摘要：

  DOI：

  10.1021/ja00180a057
• 作为产物：
  描述：

  4-甲基庚烷-3,5-二酮 在 lithium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 60.5h， 生成 2-ethyl-4-methoxy-3,5-dimethyl-2H-pyran-2-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

• Enantioselective Synthesis of the .ALPHA.-Pyrone Subunit of Verrucosidin.
  作者：Susumi HATAYAMA、Noriko OCHI、Seiichi TAKANO

  DOI：10.1248/cpb.41.1358

  日期：——

  4-Methoxyl-6-[(1S)-1-(trimethylsilyloxy)-1-methyl-2-oxobutyl]-3, 5-dimethyl-2H-pyran-2-one (4), a key α-pyrone subunit for the synthesis of verrucosidin (1), has been prepared from 6-ethyl-4-hydroxy-3, 5-dimethyl-2H-pyran-2-one (5) in an enantiomerically pure form.

  4-甲氧基-6-[(1S)-1-(三甲基硅氧基)-1-甲基-2-氧代丁基]-3, 5-二甲基-2H-吡喃-2-酮（4）是合成藜芦苷（1）的关键α-吡喃酮亚基，该化合物是由对映体纯度为 6-乙基-4-羟基-3, 5-二甲基-2H-吡喃-2-酮（5）制备而成。
• WHANG, KONGHYUN;COOKE, R. J.;OKAY, GUROL;CHA, JIN K., J. AMER. CHEM. SOC., 112,(1990) N4, C. 8985-8987
  作者：WHANG, KONGHYUN、COOKE, R. J.、OKAY, GUROL、CHA, JIN K.

  DOI：——

  日期：——
• 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.
• Total synthesis of (+)-verrucosidin
  作者：Konghyun Whang、R. J. Cooke、Gurol Okay、Jin K. Cha

  DOI：10.1021/ja00180a057

  日期：1990.11