1-(ethoxy(p-tolyl)methyl)-1H-benzotriazole | 172265-11-1

• 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-(ethoxy(p-tolyl)methyl)-1H-benzotriazole
• 英文别名: 1-[Ethoxy-(4-methylphenyl)methyl]benzotriazole
• CAS: 172265-11-1
• 化学式: C₁₆H₁₇N₃O
• 分子量: 267.33
• InChiKey: SHSDFFVLVFWDAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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-(ethoxy(p-tolyl)methyl)-1H-benzotriazole 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 0.03h， 生成 2-phenyl-2-(phenylamino)-1-(p-tolyl)ethanone
  参考文献：
  名称：

  Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones

  摘要：

  Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding alpha-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield. The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation. Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), alpha-hydroxyalkyl (12 and 13), alpha-aminoalkyl (14) and acyl(15) substituents.

  DOI：

  10.1021/jo00128a039
• 作为产物：
  描述：

  T406石油添加剂 、 对甲基苯甲醛 、 原甲酸三乙酯 在 硫酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.58h， 以72%的产率得到1-(ethoxy(p-tolyl)methyl)-1H-benzotriazole
  参考文献：
  名称：

  含酰基三氟硼酸钾（KAT）的聚合物的合成以及聚合后的连接和缀合。

  摘要：

  我们报道了用于原子转移自由基聚合（ATRP）和可逆加成-断裂链转移（RAFT）的三氟硼酸亚胺盐（TIMs）的单体合成，聚合后定量地转化为酰基三氟硼酸钾（KATs）。所得的含KAT聚合物适用于快速酰胺形成连接，用于后聚合修饰和聚合物共轭。即使在环境温度下的稀（微摩尔）水溶液条件下，聚合物的结合也能迅速发生，从而能够合成各种线性和星形嵌段共聚物。此外，我们将聚合后修饰应用于光笼环状抗生素（大蒜素S）与含KAT共聚物侧链的共价连接。

  DOI：

  10.1002/anie.202006273

文献信息

• Synthesis of Acyltrifluoroborates
  作者：Aaron M. Dumas、Jeffrey W. Bode

  DOI：10.1021/ol300668m

  日期：2012.4.20

  Acylboranes are among the most elusive boron-containing organic functional groups, a fact that has impeded development of new reactions employing them as substrates. A new synthesis of acyltrifluoroborates from benzotriazole (Bt)-based N,O-acetals has been developed. Two other routes provide acyltrifluoroborates containing alcohols, aldehydes, and carbamates. The ketone-like reactivity of the acyltrifluoroborate functional group is demonstrated, and the first X-ray structure of an acyltrifluoroborate is reported.
• Preparation of 1,2- and 1,4-diols via selective cleavage of C-benzotriazole bonds in reductive lithiations of N-(α-alkoxy-benzyl- and -allyl-)benzotriazoles
  作者：Alan R. katritzky、Weiliang Bao、Ming Qi、Clara N. Fali、Indra Prakash

  DOI：10.1016/s0040-4039(98)01390-2

  日期：1998.9

  Selective cleavage of C-benzotriazole bonds in the presence of C-O bonds is reported for the reductive lithiation of N-(alpha-alkoxybenzyl)benzotriazoles and N-(alpha-alkoxyallyl)benzotriazoles in a one-step or two-step process. Trapping of the intermediates with carbonyl compounds gave unsymmetrically protected 1,2 or 1,4-diols in moderate yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones
  作者：Alan R. Katritzky、Hengyuan Lang、Zuoquan Wang、Zhongxing Zhang、Huimin Song

  DOI：10.1021/jo00128a039

  日期：1995.11

  Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding alpha-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield. The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation. Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), alpha-hydroxyalkyl (12 and 13), alpha-aminoalkyl (14) and acyl(15) substituents.
• Synthesis of Polymers Containing Potassium Acyltrifluoroborates (KATs) and Post‐polymerization Ligation and Conjugation
  作者：Dominik Schauenburg、Mohammad Divandari、Kevin Neumann、Christoph A. Spiegel、Thomas Hackett、Yi‐Chung Dzeng、Nicholas D. Spencer、Jeffrey W. Bode

  DOI：10.1002/anie.202006273

  日期：2020.8.17

  the synthesis of monomers for atom‐transfer radical polymerization (ATRP) and a reversible addition‐fragmentation chain transfer (RAFT) agent bearing trifluoroborate iminiums (TIMs), which are quantitatively converted into potassium acyltrifluoroborates (KATs) after polymerization. The resulting KAT‐containing polymers are suitable for rapid amide‐forming ligations for both post‐polymerization modification

  我们报道了用于原子转移自由基聚合（ATRP）和可逆加成-断裂链转移（RAFT）的三氟硼酸亚胺盐（TIMs）的单体合成，聚合后定量地转化为酰基三氟硼酸钾（KATs）。所得的含KAT聚合物适用于快速酰胺形成连接，用于后聚合修饰和聚合物共轭。即使在环境温度下的稀（微摩尔）水溶液条件下，聚合物的结合也能迅速发生，从而能够合成各种线性和星形嵌段共聚物。此外，我们将聚合后修饰应用于光笼环状抗生素（大蒜素S）与含KAT共聚物侧链的共价连接。