1-[(4-Chlorophenyl)-ethoxymethyl]benzotriazole

• 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-[(4-Chlorophenyl)-ethoxymethyl]benzotriazole
• 化学式: C₁₅H₁₄ClN₃O
• 分子量: 287.749
• InChiKey: XNHBWJXIHNMNLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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-[(4-Chlorophenyl)-ethoxymethyl]benzotriazole 在 正丁基锂 、 硼酸三甲酯 、 potassium hydrogen bifluoride 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.12h， 以41%的产率得到4-氯苯甲酰基三氟硼酸钾
  参考文献：
  名称：

  Synthesis of Acyltrifluoroborates

  摘要：

  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.

  DOI：

  10.1021/ol300668m
• 作为产物：
  描述：

  T406石油添加剂 、 乙醇 、 4-氯苯甲醛 在 硫酸 、 原甲酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 14.25h， 生成 、 1-[(4-Chlorophenyl)-ethoxymethyl]benzotriazole
  参考文献：
  名称：

  Synthesis of Acyltrifluoroborates

  摘要：

  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.

  DOI：

  10.1021/ol300668m

文献信息

• Novel and Efficient Insertions of Carbons Carrying O-, S-, and N-Linked Substituents:  Synthesis of α-Alkoxyalkyl, α-(Alkylthio)alkyl, and α-(Carbazol-9-yl)alkyl Ketones
  作者：Alan R. Katritzky、Linghong Xie、Larisa Serdyuk

  DOI：10.1021/jo960840p

  日期：1996.1.1

  A wide variety of benzotriazolyl-stabilized anions 2, obtained by the lithiation of 1-(alpha-alkoxyalkyl)-, 1-[alpha-(alkylthio)alkyl]-, and 1-[alpha-(carbazol-9-yl)alkyl]benzotriazoles 1, on reaction with aliphatic and aromatic aldehydes and ketones, followed by rearrangement induced by heating in the presence of zinc bromide, furnish one-carbon-homologated alpha-alkoxyalkyl, alpha-(alkylthio)alkyl

  通过1-（α-烷氧基烷基）-，1- [α-（烷硫基）烷基]-和1- [α-（咔唑-9-基）烷基的锂化获得的各种苯并三唑基稳定的阴离子2 ]苯并三唑1，与脂肪族和芳香族醛和酮反应，然后在溴化锌存在下通过加热引发重排，提供一碳均一的α-烷氧基烷基，α-（烷硫基）烷基和α-（咔唑-简单的一锅操作中的9-基）烷基酮4收率高，区域选择性好。在数个烷氧基亚甲基插入中，中间体2-烷氧基氧杂环丁烷的收率高，这表明了重排的环氧机理，为另一类重要化合物多取代的2-烷氧基氧杂环丁烷提供了简便的方法。
• General and Efficient Carbon Insertion Route to One-Carbon-Homologated .alpha.-Aryl, .alpha.-Alkenyl, .alpha.-Alkoxy, and .alpha.-Phenylthio Alkyl Ketones
  作者：Alan R. Katritzky、Linghong Xie、Dorin Toader、Larisa Serdyuk

  DOI：10.1021/ja00153a032

  日期：1995.12
• Synthesis of β-Alkoxy Ketones and α‘-Functionalized β-Alkoxy Ketones Utilizing Benzotriazole-Stabilized Acyl Anion Synthons
  作者：Alan R. Katritzky、Daming Feng、Ming Qi

  DOI：10.1021/jo971630v

  日期：1998.3.1

  1-(alpha-Alkoxyalkyl)benzotriazoles 1a-d add to phenyl vinyl ether to form key intermediates 4a-d, which readily undergo lithiation and subsequent trapping by a variety of electrophiles to give the expected substituted derivatives 7a-d, 9a-c, 11, 13, 15, and 18 in high yields. Subsequent hydrolysis of these compounds provides a novel high-yield acyl anion synthon approach for the synthesis of beta-alkoxy ketones 8 or alpha'-functionalized beta-alkoxy ketones 10, 12, 14, 16, and 19 by short procedures from readily available starting materials.