9-<3-(Benzotriazol-1-yl)-3-ethoxyallyl>-9-hydroxyfluorene

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-<3-(Benzotriazol-1-yl)-3-ethoxyallyl>-9-hydroxyfluorene
• 英文别名: 9-[(E)-3-(benzotriazol-1-yl)-3-ethoxyprop-2-enyl]fluoren-9-ol
• 化学式: C₂₄H₂₁N₃O₂
• 分子量: 383.45
• InChiKey: WNFHFLYMJJGOLP-HZHRSRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-<3-(Benzotriazol-1-yl)-3-ethoxyallyl>-9-hydroxyfluorene 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(fluoren-9-ylidene)propionic acid
  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：

  9-芴酮 、 1-(1-乙氧基-2-丙烯-1-基)-1H-苯并三唑 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到9-<3-(Benzotriazol-1-yl)-3-ethoxyallyl>-9-hydroxyfluorene
  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