Ethyl 1-(benzotriazol-1-yl)-1-propenyl ether | 158321-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: Ethyl 1-(benzotriazol-1-yl)-1-propenyl ether
• 英文别名: 1H-1,2,3-benzotriazole, 1-[(1E)-1-ethoxy-1-propenyl]-；1-[(E)-1-ethoxyprop-1-enyl]benzotriazole
• CAS: 158321-87-0
• 化学式: C₁₁H₁₃N₃O
• 分子量: 203.244
• InChiKey: FFINPDBVAZLCGK-QDEBKDIKSA-N

物化性质

• 沸点：
  328.7±35.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  Ethyl 1-(benzotriazol-1-yl)-1-propenyl ether 、 3-甲基苯甲醛 在 正丁基锂 作用下， 生成 cis-1-<7-<(3-methylphenyl)hydroxymethyl>benzotriazol-1-yl>-1-ethoxypropene
  参考文献：
  名称：

  Katritzky, Alan R.; Ignatchenko, Alexey V.; Lang, Hengyuan, Heterocycles, 1995, vol. 41, # 1, p. 131 - 146

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氯苯并三氮唑 在 正丁基锂 、 potassium tert-butylate 作用下， 反应 5.0h， 生成 Ethyl 1-(benzotriazol-1-yl)-1-propenyl ether
  参考文献：
  名称：

  Benzotriazole-assisted β-lithiation of vinyl ethers

  摘要：

  Benzotriazole-assisted beta-deprotonation of (alpha-benzotriazolylvinyl) ethers occurs stereoselectively at the cis position as shown by quenching with a variety of electrophiles. Semiempirical calculations of the lithiated enol ethers by PM3 and MNDO methods disclosed a higher stabilization for the cis-isomers over the corresponding trans-isomers.

  DOI：

  10.1016/s0040-4020(01)90453-3

文献信息

• Novel Routes to Enol Ethers, Unsymmetrical Ketones, .alpha.-Bromoalkyl Ketones, 1,4-Diketones, 2-Ethoxy-2-cyclopentenones, and .alpha.-Keto Enamines
  作者：Alan R. Katritzky、Guifen Zhang、Jinlong Jiang

  DOI：10.1021/jo00128a037

  日期：1995.11

  Highly regioselective S(N)2' reactions of adducts 6 (readily prepared by reactions of halides with the allyl anion 12 of 11) with Grignard reagents gave enol ethers 13, which were converted (in one-pot reactions from 11) into ketones 14 and alpha-bromoalkyl ketones 15 in good yields. The monoprotected 1,4-diketone derivative 16 (prepared by Michael addition of the allyl anion 12 with methyl vinyl ketone) was converted both into 1,4-diketones 18 and into protected gamma-hydroxyalkyl ketone 20 by selective Grignard reactions, which could be directed either to the carbonyl, or the protected propenoyl, or to both functionalities. The allyl anion 12 with alpha-substituted acetic esters gave alpha-acylated adducts 24, which underwent in situ unfavored endo-trig cyclization upon treatment with NaH and secondary amines, to give 2-ethoxy-2-cyclopentenones 27 and 28 and alpha-keto enamines 25 in good yield. The mechanism for the cyclization is discussed.
• Katritzky Alan R., Ignatchenko Alexey V., Lan Xiangfu, Lang Hengyuan, Ste+, Tetrahedron, 50 (1994) N 20, S 6005-6016
  作者：Katritzky Alan R., Ignatchenko Alexey V., Lan Xiangfu, Lang Hengyuan, Ste+

  DOI：——

  日期：——
• Benzotriazole-assisted β-lithiation of vinyl ethers
  作者：Alan R. Katritzky、Alexey V. Ignatchenko、Xiangfu Lan、Hengyuan Lang、Christian V. Stevens、Andreas Opitz、Rainer Koch、Ernst Anders

  DOI：10.1016/s0040-4020(01)90453-3

  日期：1994.1

  Benzotriazole-assisted beta-deprotonation of (alpha-benzotriazolylvinyl) ethers occurs stereoselectively at the cis position as shown by quenching with a variety of electrophiles. Semiempirical calculations of the lithiated enol ethers by PM3 and MNDO methods disclosed a higher stabilization for the cis-isomers over the corresponding trans-isomers.
• Katritzky, Alan R.; Ignatchenko, Alexey V.; Lang, Hengyuan, Heterocycles, 1995, vol. 41, # 1, p. 131 - 146
  作者：Katritzky, Alan R.、Ignatchenko, Alexey V.、Lang, Hengyuan

  DOI：——

  日期：——

表征谱图