[2-Methyl-4-(3-methylfuran-2-yl)butan-2-yl] acetate | 154876-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: [2-Methyl-4-(3-methylfuran-2-yl)butan-2-yl] acetate
• CAS: 154876-04-7
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: GRHWWSZCKRODGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-Methyl-4-(3-methylfuran-2-yl)butan-2-yl] acetate 在 lithium hydroxide 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 42.0h， 生成 3-甲基-2-(3-甲基-2-丁烯基)呋喃
  参考文献：
  名称：

  A Practical Synthesis of Rosefuran. Furans from Acetylenes and Allyl Alcohols

  摘要：

  A new atom-economical synthetic strategy for the synthesis of furans emerges from beta,gamma-unsaturated ketones which are readily available from acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans are available in two steps from allyl alcohols and acetylenes with only water as the byproduct. A straightforward synthesis of the prized fragrance of oil of rose, rosefuran, from propargyl bromide, acetone, and 1-buten-3-ol in 23% overall yield illustrates the utility of this new strategy.

  DOI：

  10.1021/jo00084a026
• 作为产物：
  描述：

  7-乙酰氧基-3,7-二甲基-1-辛烯-4-酮 在 N-甲基吗啉 、 四氧化锇 、 对甲苯磺酸 作用下， 生成 [2-Methyl-4-(3-methylfuran-2-yl)butan-2-yl] acetate
  参考文献：
  名称：

  A Practical Synthesis of Rosefuran. Furans from Acetylenes and Allyl Alcohols

  摘要：

  A new atom-economical synthetic strategy for the synthesis of furans emerges from beta,gamma-unsaturated ketones which are readily available from acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans are available in two steps from allyl alcohols and acetylenes with only water as the byproduct. A straightforward synthesis of the prized fragrance of oil of rose, rosefuran, from propargyl bromide, acetone, and 1-buten-3-ol in 23% overall yield illustrates the utility of this new strategy.

  DOI：

  10.1021/jo00084a026

文献信息

• A Practical Synthesis of Rosefuran. Furans from Acetylenes and Allyl Alcohols
  作者：Barry M. Trost、John A. Flygare

  DOI：10.1021/jo00084a026

  日期：1994.3

  A new atom-economical synthetic strategy for the synthesis of furans emerges from beta,gamma-unsaturated ketones which are readily available from acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans are available in two steps from allyl alcohols and acetylenes with only water as the byproduct. A straightforward synthesis of the prized fragrance of oil of rose, rosefuran, from propargyl bromide, acetone, and 1-buten-3-ol in 23% overall yield illustrates the utility of this new strategy.