1-((E)-1-Ethoxy-3-phenyl-allyl)-1H-[1,2,4]triazole | 136290-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-((E)-1-Ethoxy-3-phenyl-allyl)-1H-[1,2,4]triazole
• 英文别名: 1-[(E)-1-ethoxy-3-phenylprop-2-enyl]-1,2,4-triazole
• CAS: 136290-37-4
• 化学式: C₁₃H₁₅N₃O
• 分子量: 229.282
• InChiKey: QMMSNFDZRHOALP-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((E)-1-Ethoxy-3-phenyl-allyl)-1H-[1,2,4]triazole 在 盐酸 、 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 8.08h， 生成 4,5-diphenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Benzotriazole- and 1,2,4-Triazole-Stabilized Allylic Anions:  Applications in Syntheses of Functionalized α,β-Unsaturated Ketones, γ-Lactones, γ-Lactams, and β-Substituted Esters

  摘要：

  Deprotonated 1-(benzotriazol-1-yl)-1-ethoxy-2-hexene (7) reacted with alkyl halides, aldehydes, ketones, imines, and alpha-beta-unsaturated esters to give exclusively the alpha-alkylated products 8a-c, 10a,b, 12, 14, 16, and 18a,b, respectively. Without isolation, these products were hydrolyzed under mild conditions to generate the corresponding simple or functionalized alpha,beta-unsaturated ketones 9a-c, 11a,b, 13, 15, 17, and 19a,b. Similar reactions with the phenyl-substituted analog 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene (21) also gave the analogous alpha-products, but they were accompanied by small amount of the gamma-products in most cases. By contrast, deprotonation of the corresponding triazole derivative 29 with butyllithium followed by reactions with alkyl halides, aldehydes, ketones, or imines yielded exclusively gamma-alkylated adducts 32, 34, 36, 38, 40, and 42. Intermediates 32, 34, 36, 38, 40, and 42 were readily converted into beta-substituted esters 33a-c, gamma-lactones 35a,b, 39, 41, and 43, and gamma-lactams 37a-c on hydrolysis.

  DOI：

  10.1021/jo961396t
• 作为产物：
  描述：

  (E)-(3,3-二乙氧基-1-丙烯基)苯 、 1H-1,2,4-三唑 以57%的产率得到
  参考文献：
  名称：

  OHTA, SHUNSAKU;MARUYAMA, AKIHIKO;KAWASAKI, IKUO;HATAKEYAMA, SHOKO;ICHIKAW+, HETEROCYCLES, 31,(1990) N1, C. 2029-2036

  摘要：

  DOI：

文献信息

• OHTA, SHUNSAKU;MARUYAMA, AKIHIKO;KAWASAKI, IKUO;HATAKEYAMA, SHOKO;ICHIKAW+, HETEROCYCLES, 31,(1990) N1, C. 2029-2036
  作者：OHTA, SHUNSAKU、MARUYAMA, AKIHIKO、KAWASAKI, IKUO、HATAKEYAMA, SHOKO、ICHIKAW+

  DOI：——

  日期：——
• Benzotriazole- and 1,2,4-Triazole-Stabilized Allylic Anions:  Applications in Syntheses of Functionalized α,β-Unsaturated Ketones, γ-Lactones, γ-Lactams, and β-Substituted Esters
  作者：Alan R. Katritzky、Daming Feng、Hengyuan Lang

  DOI：10.1021/jo961396t

  日期：1997.2.1

  Deprotonated 1-(benzotriazol-1-yl)-1-ethoxy-2-hexene (7) reacted with alkyl halides, aldehydes, ketones, imines, and alpha-beta-unsaturated esters to give exclusively the alpha-alkylated products 8a-c, 10a,b, 12, 14, 16, and 18a,b, respectively. Without isolation, these products were hydrolyzed under mild conditions to generate the corresponding simple or functionalized alpha,beta-unsaturated ketones 9a-c, 11a,b, 13, 15, 17, and 19a,b. Similar reactions with the phenyl-substituted analog 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene (21) also gave the analogous alpha-products, but they were accompanied by small amount of the gamma-products in most cases. By contrast, deprotonation of the corresponding triazole derivative 29 with butyllithium followed by reactions with alkyl halides, aldehydes, ketones, or imines yielded exclusively gamma-alkylated adducts 32, 34, 36, 38, 40, and 42. Intermediates 32, 34, 36, 38, 40, and 42 were readily converted into beta-substituted esters 33a-c, gamma-lactones 35a,b, 39, 41, and 43, and gamma-lactams 37a-c on hydrolysis.