1-<(Benzotriazol-1-yl)ethoxymethyl>naphthalene | 172265-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-<(Benzotriazol-1-yl)ethoxymethyl>naphthalene
• 英文别名: 1-[Ethoxy(naphthalen-1-yl)methyl]benzotriazole
• CAS: 172265-12-2
• 化学式: C₁₉H₁₇N₃O
• 分子量: 303.363
• InChiKey: KFRJPIXQDMVHJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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-<(Benzotriazol-1-yl)ethoxymethyl>naphthalene 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-hydroxy-2-methyl-1-(1-naphthyl)propan-1-one
  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 、 1-萘甲醛 、 原甲酸三乙酯 在 硫酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以71%的产率得到1-<(Benzotriazol-1-yl)ethoxymethyl>naphthalene
  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

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.
• 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.