1-[(E)-but-2-enyl]benzotriazole | 213665-41-9

• 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: 1-[(E)-but-2-enyl]benzotriazole
• CAS: 213665-41-9
• 化学式: C₁₀H₁₁N₃
• 分子量: 173.217
• InChiKey: NAYIRQVZHADYFX-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-二苯基丙酮 、 1-[(E)-but-2-enyl]benzotriazole 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-3-(benzotriazol-1-yl)-2-methyl-1,1-diphenylhex-4-en-2-ol
  参考文献：
  名称：

  Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

  摘要：

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

  DOI：

  10.1021/jo980616v
• 作为产物：
  描述：

  1-(三甲基硅基)苯并三氮唑 、 (E)-巴豆氯 以91%的产率得到
  参考文献：
  名称：

  GASPARINI J. P.; GASSEND R.; MAIRE J. C., J. ORGANOMETAL. CHEM., 1980, 188, NO 2, 141-150

  摘要：

  DOI：

文献信息

• The Mitsunobu Reaction: An Alternative Synthesis of 1-(Primary Alkyl)benzotriazoles
  作者：Alan R. Katritzky、Daniela C. Oniciu、Ion Ghiviriga

  DOI：10.1080/00397919708006100

  日期：1997.5

  by treating the corresponding alcohol with triphenylphosphine, N-bromosuccinimide and benzotriazole. Under these conditions, the alcohols gave exclusively the corresponding 1-alkyl-benzotriazoles. Allyl and propargyl alcohols also reacted regiospecifically in a typical Sn2 manner, and no products derived from prototropic rearrangement were found.

  摘要 1-（伯烷基）苯并三唑可以通过用三苯基膦、N-溴代琥珀酰亚胺和苯并三唑处理相应的醇以方便的收率获得。在这些条件下，醇只产生相应的 1-烷基-苯并三唑。烯丙醇和炔丙醇也以典型的 Sn2 方式进行区域特异性反应，并且没有发现源自质子重排的产物。
• Palladium-Catalyzed Reaction of <i>N-</i>Allylbenzotriazoles with Amines:  A Novel Method for the Preparation of Allylamines
  作者：Alan R. Katritzky、Jiangchao Yao、Ming Qi

  DOI：10.1021/jo980200h

  日期：1998.7.1
• Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation
  作者：Alan R. Katritzky、Dai Cheng、Scott A. Henderson、Jianqing Li

  DOI：10.1021/jo980616v

  日期：1998.9.1

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.
• GASPARINI J. P.; GASSEND R.; MAIRE J. C., J. ORGANOMETAL. CHEM., 1980, 188, NO 2, 141-150
  作者：GASPARINI J. P.、 GASSEND R.、 MAIRE J. C.

  DOI：——

  日期：——