3-(benzotriazol-1-yl)-2-(tert-butyl)-3-phenyl-2-propenol | 627088-05-5

• 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: 3-(benzotriazol-1-yl)-2-(tert-butyl)-3-phenyl-2-propenol
• 英文别名: 2-[benzotriazol-1-yl(phenyl)methylidene]-3,3-dimethylbutan-1-ol
• CAS: 627088-05-5
• 化学式: C₁₉H₂₁N₃O
• 分子量: 307.395
• InChiKey: LXLACSGMPHERRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  50.94
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(benzotriazol-1-yl)-2-(tert-butyl)-3-phenyl-2-propenol 在 镍 草酰氯 、 氢气 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 [1-(2-aminophenyl)-4-tert-butyl-5-phenyl-1H-pyrazol-3-yl]phenylamine
  参考文献：
  名称：

  A novel synthesis of 4,5-diaryl-6-arylamino-2,3-benzo-1,3a,6a-triazapentalenes

  摘要：

  Treatment of N-alkyl- and N-aryl-imines of 2,3-diaryl- and 2-alkyl-3-aryl-3-(benzotriazol-1-yl)propenals with trifluoroacetic anhydride in THF at room temperature gave 5-alkyl-4-aryl-6-[N-alkyl (and aryl)-N-trifluoroacetyl]amino-2,3-benzo-1,3a,6a-triazapentalenes in moderate to good yields. On heating triazapentalenes having R-2 = aryl in MeOH at reflux, detrifluoroacetylation of triazapentalene occurred to give title compounds in good yields. However, the same treatment of triazapentalenes having R-2=alkyl did not give the corresponding detrifluoroacetylation product. The title compounds and 5-alkyl-4-aryl-6-(N-alkyl-N-trifluoroacetyl)amino-2,3-benzo-1,3a,6a-triazapentalenes were found to be good precursors for the synthesis of 1-(o-aminophenyl)-3-arylamino-4-alkyl (and aryl)-5-arylpyrazoles and 1-(o-aminophenyl)-3-(N-alkyl-N-trifluoroacetyl)amino-4-alkyl (and aryl)-5-arylpyrazoles, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.012
• 作为产物：
  描述：

  1-苄基-1H-苯并三唑 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 3-(benzotriazol-1-yl)-2-(tert-butyl)-3-phenyl-2-propenol
  参考文献：
  名称：

  A novel synthesis of 4,5-diaryl-6-arylamino-2,3-benzo-1,3a,6a-triazapentalenes

  摘要：

  Treatment of N-alkyl- and N-aryl-imines of 2,3-diaryl- and 2-alkyl-3-aryl-3-(benzotriazol-1-yl)propenals with trifluoroacetic anhydride in THF at room temperature gave 5-alkyl-4-aryl-6-[N-alkyl (and aryl)-N-trifluoroacetyl]amino-2,3-benzo-1,3a,6a-triazapentalenes in moderate to good yields. On heating triazapentalenes having R-2 = aryl in MeOH at reflux, detrifluoroacetylation of triazapentalene occurred to give title compounds in good yields. However, the same treatment of triazapentalenes having R-2=alkyl did not give the corresponding detrifluoroacetylation product. The title compounds and 5-alkyl-4-aryl-6-(N-alkyl-N-trifluoroacetyl)amino-2,3-benzo-1,3a,6a-triazapentalenes were found to be good precursors for the synthesis of 1-(o-aminophenyl)-3-arylamino-4-alkyl (and aryl)-5-arylpyrazoles and 1-(o-aminophenyl)-3-(N-alkyl-N-trifluoroacetyl)amino-4-alkyl (and aryl)-5-arylpyrazoles, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.012

文献信息

• A Novel Method for the Synthesis of 2,3-Benzo-1,3a,6a-triazapentalenes through Pummerer-Type Reactions of γ-(Benzotriazol-1-yl)allylic Sulfoxides
  作者：Taehoon Kim、Kyongtae Kim、Yung Ja Park

  DOI：10.1002/1099-0690(20022)2002:3<493::aid-ejoc493>3.0.co;2-b

  日期：2002.2

  Treatment of 1-(arylmethyl)benzotriazoles 1 with nBuLi in THF at −78 °C, followed by addition of 1-aryl-2-chloroethanones, gave diastereomeric mixtures of 1-[(aryl)(benzotriazol-1-yl)methyl]oxiranes 2. Treatment of 2 with nBuLi in THF at −78 °C, followed by acidification, afforded a mixture of (E)- and (Z)-allylic alcohols 3, which were converted into 1,2-disubstituted 2-(alkyl- or aryl)-1-(benzotr

  在-78°C 的 THF 中用 nBuLi 处理 1-（芳基甲基）苯并三唑 1，然后加入 1-芳基-2-氯乙酮，得到 1-[（芳基）（苯并三唑-1-基）甲基] 的非对映异构混合物环氧乙烷 2. 在-78 °C 的 THF 中用 nBuLi 处理 2，然后酸化，得到 (E)- 和 (Z)-烯丙醇 3 的混合物，将其转化为 1,2-二取代的 2-(烷基- 或芳基)-1-(苯并三唑-1-基)-3-硫烷基丙烯 5 通过相应的烯丙基氯化物 4. 在室温下在 CH2Cl2 中通过 mCPBA 氧化硫化物 5，然后在室温下用三氟乙酸酐 (TFAA) 处理，以良好的产率得到标题化合物。发现在氢气和回流下在 EtOH 中用 Raney-Ni 处理标题化合物以极好的收率得到 2-(吡唑-1-基)苯胺衍生物。