3,4-Epoxy-3-ethoxy-4-methyloct-1-ene | 161607-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 3,4-Epoxy-3-ethoxy-4-methyloct-1-ene
• 英文别名: 2-Butyl-3-ethenyl-3-ethoxy-2-methyloxirane
• CAS: 161607-27-8
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: XPSMOZMDTPJSAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-Epoxy-3-ethoxy-4-methyloct-1-ene 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-Hydroxy-1-methoxy-4-methyl-3-octanone
  参考文献：
  名称：

  A Novel Heterocycle-Stabilized Allylic Anion Route to Cyclopropanes, 1-Ethoxy-1-vinylethylene Oxides, 1-Hydroxyalkyl 2-Methoxyethyl Ketones, 1-Hydroxyalkyl Vinyl Ketones, .beta.-Ethoxy-.beta.-vinylalkyl Alcohols, .gamma.-Lactones, and .beta.,.gamma.-Unsaturated Carboxylic Acids

  摘要：

  Treatment of N-(alpha-ethoxyallyl)benzotriazole (8) with butyllithium followed by alpha,beta-unsaturated esters at -78 degrees C formed the 1,1-adducts 11 which underwent internal displacement of the benzotriazolyl group at 20 degrees C to give cyclopropanecarboxylic esters 14 and 15. In the presence of ZnBr2, addition of anion 13 to cyclic and methyl ketones gave 1-ethoxy-1-vinylethylene oxides 25 in good yields. Epoxides 25 were subsequently converted to 1-hydroxyalkyl 2-methoxyethyl ketones 24, 1-hydroxyalkyl vinyl ketones 26, and beta-ethoxy-beta-vinylalkyl alcohols 27. Treatment of anion 13 with aromatic ketones or sterically hindered aliphatic ketones produced gamma-alkylated adducts 31 which were hydrolyzed to beta,gamma-unsaturated carboxylic acids 32 (R(1), R(2) = aromatic) or gamma-lactones 33 (R(1), R(2) = aliphatic).

  DOI：

  10.1021/jo00128a036
• 作为产物：
  描述：

  2-己酮 在 正丁基锂 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 18.17h， 生成 3,4-Epoxy-3-ethoxy-4-methyloct-1-ene
  参考文献：
  名称：

  A Novel Heterocycle-Stabilized Allylic Anion Route to Cyclopropanes, 1-Ethoxy-1-vinylethylene Oxides, 1-Hydroxyalkyl 2-Methoxyethyl Ketones, 1-Hydroxyalkyl Vinyl Ketones, .beta.-Ethoxy-.beta.-vinylalkyl Alcohols, .gamma.-Lactones, and .beta.,.gamma.-Unsaturated Carboxylic Acids

  摘要：

  Treatment of N-(alpha-ethoxyallyl)benzotriazole (8) with butyllithium followed by alpha,beta-unsaturated esters at -78 degrees C formed the 1,1-adducts 11 which underwent internal displacement of the benzotriazolyl group at 20 degrees C to give cyclopropanecarboxylic esters 14 and 15. In the presence of ZnBr2, addition of anion 13 to cyclic and methyl ketones gave 1-ethoxy-1-vinylethylene oxides 25 in good yields. Epoxides 25 were subsequently converted to 1-hydroxyalkyl 2-methoxyethyl ketones 24, 1-hydroxyalkyl vinyl ketones 26, and beta-ethoxy-beta-vinylalkyl alcohols 27. Treatment of anion 13 with aromatic ketones or sterically hindered aliphatic ketones produced gamma-alkylated adducts 31 which were hydrolyzed to beta,gamma-unsaturated carboxylic acids 32 (R(1), R(2) = aromatic) or gamma-lactones 33 (R(1), R(2) = aliphatic).

  DOI：

  10.1021/jo00128a036

文献信息

• A Novel Heterocycle-Stabilized Homoenolate Anion and Its Applications in the Syntheses of .beta.-Propenoylcarboxylic Esters, Cyclopropanecarboxylic Esters, 1-Vinyl-1-ethoxy Epoxides, and .gamma.-Lactones
  作者：Alan R. Katritzky、Jinlong Jiang

  DOI：10.1021/jo00106a003

  日期：1995.1
• A Novel Heterocycle-Stabilized Allylic Anion Route to Cyclopropanes, 1-Ethoxy-1-vinylethylene Oxides, 1-Hydroxyalkyl 2-Methoxyethyl Ketones, 1-Hydroxyalkyl Vinyl Ketones, .beta.-Ethoxy-.beta.-vinylalkyl Alcohols, .gamma.-Lactones, and .beta.,.gamma.-Unsaturated Carboxylic Acids
  作者：Alan R. Katritzky、Jinlong Jiang

  DOI：10.1021/jo00128a036

  日期：1995.11

  Treatment of N-(alpha-ethoxyallyl)benzotriazole (8) with butyllithium followed by alpha,beta-unsaturated esters at -78 degrees C formed the 1,1-adducts 11 which underwent internal displacement of the benzotriazolyl group at 20 degrees C to give cyclopropanecarboxylic esters 14 and 15. In the presence of ZnBr2, addition of anion 13 to cyclic and methyl ketones gave 1-ethoxy-1-vinylethylene oxides 25 in good yields. Epoxides 25 were subsequently converted to 1-hydroxyalkyl 2-methoxyethyl ketones 24, 1-hydroxyalkyl vinyl ketones 26, and beta-ethoxy-beta-vinylalkyl alcohols 27. Treatment of anion 13 with aromatic ketones or sterically hindered aliphatic ketones produced gamma-alkylated adducts 31 which were hydrolyzed to beta,gamma-unsaturated carboxylic acids 32 (R(1), R(2) = aromatic) or gamma-lactones 33 (R(1), R(2) = aliphatic).