4-Acetyl-2-methoxy-3-methylenetetrahydrofuran ethylene ketal | 150808-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Acetyl-2-methoxy-3-methylenetetrahydrofuran ethylene ketal
• 英文别名: 2-(5-Methoxy-4-methylideneoxolan-3-yl)-2-methyl-1,3-dioxolane
• CAS: 150808-67-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: GFNKQEQJVYBHRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Acetyl-2-methoxy-3-methylenetetrahydrofuran ethylene ketal 在 palladium on activated charcoal 硫酸 、 氢气 、 silica gel 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.25h， 生成 球二孢菌素
  参考文献：
  名称：

  Allenyl ethers as precursors of .alpha.-methylene-.gamma.-butyrolactones and botryodiplodin derivatives

  摘要：

  Beta-Bromopropargyl ethers 2a-h, 11, and 12 or allyl propargyl ethers 8d-h are easily isomerized with potassium tert-butoxide (KO-t-Bu) into the corresponding allenyl derivatives 3a-h, 13, 14, and 9d-h. These compounds afford alpha-methylene-gamma-butyrolactones 7a-h, 25, and 26 by application of the sequence halogenation/dehydrohalogenation/homolytic carbocyclization. Starting from methyl vinyl ketone 1i, similar transformations lead to botryodiplodin (27) or ethoxybotryodiplodin (28).

  DOI：

  10.1021/jo00073a033
• 作为产物：
  描述：

  3-Bromo-4-(1,2-propadienyloxy)butan-2-one ethylene ketal 在 18-冠醚-6 sodium hydroxide 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 (4-methylpent-4-enyl)bis(dimethylglyoximato)(pyridine)cobalt(III) 、 potassium tert-butylate 作用下， 以 乙醇 、 丙酮 、 苯 为溶剂， 反应 6.5h， 生成 4-Acetyl-2-methoxy-3-methylenetetrahydrofuran ethylene ketal
  参考文献：
  名称：

  Allenyl ethers as precursors of .alpha.-methylene-.gamma.-butyrolactones and botryodiplodin derivatives

  摘要：

  Beta-Bromopropargyl ethers 2a-h, 11, and 12 or allyl propargyl ethers 8d-h are easily isomerized with potassium tert-butoxide (KO-t-Bu) into the corresponding allenyl derivatives 3a-h, 13, 14, and 9d-h. These compounds afford alpha-methylene-gamma-butyrolactones 7a-h, 25, and 26 by application of the sequence halogenation/dehydrohalogenation/homolytic carbocyclization. Starting from methyl vinyl ketone 1i, similar transformations lead to botryodiplodin (27) or ethoxybotryodiplodin (28).

  DOI：

  10.1021/jo00073a033

文献信息

• Allenyl ethers as precursors of .alpha.-methylene-.gamma.-butyrolactones and botryodiplodin derivatives
  作者：Jean Pierre Dulcere、Mohamed Naceur Mihoubi、Jean Rodriguez

  DOI：10.1021/jo00073a033

  日期：1993.10

  Beta-Bromopropargyl ethers 2a-h, 11, and 12 or allyl propargyl ethers 8d-h are easily isomerized with potassium tert-butoxide (KO-t-Bu) into the corresponding allenyl derivatives 3a-h, 13, 14, and 9d-h. These compounds afford alpha-methylene-gamma-butyrolactones 7a-h, 25, and 26 by application of the sequence halogenation/dehydrohalogenation/homolytic carbocyclization. Starting from methyl vinyl ketone 1i, similar transformations lead to botryodiplodin (27) or ethoxybotryodiplodin (28).