1-(1-ethoxyethyl)-1H-benzo[d][1,2,3]triazole | 23269-46-7

• 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-(1-ethoxyethyl)-1H-benzo[d][1,2,3]triazole
• 英文别名: 1-(1-Ethoxyethyl)benzotriazole
• CAS: 23269-46-7
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: UWFQEWIJLURXRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-(1-ethoxyethyl)-1H-benzo[d][1,2,3]triazole 生成 乙醇
  参考文献：
  名称：

  POJER P. M., AUSTRAL. J. CHEM., 1979, 32, NO 12, 2787-2791

  摘要：

  DOI：
• 作为产物：
  描述：

  T406石油添加剂 在 对甲苯磺酸 作用下， 以 various solvent(s) 为溶剂， 反应 21.0h， 生成 1-(1-ethoxyethyl)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Lewis Acid-Catalyzed Additions of (Benzotriazol-1-yl)diethoxymethane to Enol Ethers and Enamides. New Syntheses of β-Alkoxyalkanal and β-Aminoalkanal Acetals

  摘要：

  Addition of (benzotriazol-1-yl)diethoxymethane 11 to various acyclic and cyclic enol ethers and enamides produces the corresponding adducts, which were reacted with either NaAlH4 or Grignard reagents to afford acyclic acetal-ethers (18a-f), cyclic alpha-(substituted)-beta-acetals (19a-c), amino-acetals (24a,b), and 1,3-amino-ethers (25), all known but previously difficult-to-access classes of compounds.

  DOI：

  10.1021/jo9612335

文献信息

• Ruthenium-Catalyzed C–H Bond Activation Approach to Azolyl Aminals and Hemiaminal Ethers, Mechanistic Evaluations, and Isomer Interconversion
  作者：Manish K. Singh、Hari K. Akula、Sakilam Satishkumar、Lothar Stahl、Mahesh K. Lakshman

  DOI：10.1021/acscatal.5b02603

  日期：2016.3.4

  reactions between benzotriazole and 5,6-dimethylbenzotriazole with N-methylpyrrolidinone, tetrahydrofuran, tetrahydropyran, diethyl ether, 1,4-dioxane, and isochroman have been conducted using RuCl3·3H2O/t-BuOOH in 1,2-dichloroethane. In all cases, N1 and N2 alkylation products were obtained, and these are readily separated by chromatography. One of these products, 1-(isochroman-1-yl)-5,6-dimethyl-1H-benzotriazole

  苯并三唑和5,6-二甲基苯并三唑与N-甲基吡咯烷酮，四氢呋喃，四氢吡喃，乙醚，1,4-二恶烷和异铬烷之间的C（sp 3）–N键形成反应已使用RuCl 3 ·3H 2 O / 1,2-二氯乙烷中的叔丁基。在所有情况下，均获得N 1和N 2烷基化产物，并且可以通过色谱法容易地分离它们。这些产品之一，1-（异色满-1-基）-5,6-二甲基-1 HX射线晶体学检查了-苯并三唑。这是第一个通过此方法分析的此类化合物，尤其是，苯并三唑基部分是准轴向排列的，与异头作用一致。这具有合理的后果，以前没有观察到。与其他通过自由基进行的生成半甲醚的反应相反，在自由基抑制剂的存在下，这种Ru催化的过程不会受到抑制。因此，据信发生了由氧钌物种介导的氧碳intermediate中间体的快速形成。在自由基捕获实验中，已经鉴定出同时含有苯并三唑和TEMPO单元的未知产物。在这些产品中，苯并三唑很可能是通过Ru催化的C–N
• Metal-Free Tandem Oxidative Coupling of Primary Alcohols with Azoles for the Synthesis of Hemiaminal Ethers
  作者：Jinwei Sun、Yu Zhang、Sankaran Mathan、Yi Wang、Yi Pan

  DOI：10.1021/acs.joc.5b02516

  日期：2016.4.15

  A novel metal-free tandem oxidative coupling process for the synthesis of hemiaminal ethers has been developed. This protocol could be applied for the C–N bond formation of electron-deficient trizoles, tetrazoles, carbazoles and indazoles with primary alcohols.

  已开发出一种新颖的无金属串联氧化偶联方法，用于合成半胱氨酸醚。该方案可用于缺电子的三唑，四唑，咔唑和吲唑与伯醇的C–N键形成。
• <i>o</i>-(α-Benzotriazolylalkyl)phenols: Novel Precursors of<i>o</i>-Quinone Methides
  作者：Alan >r. Katritzky、Xiangfu Lan

  DOI：10.1055/s-1992-26221

  日期：——

  1-[α-(Benzotriazol-1-yl)alkyl]-2-napthols and 2-[(benzotriazol-1-yl)-methyl]phenols have been shown to lose a molecule of benzotriazole to generate o-quinone methides, which can be trapped with electron-rich olefins (ethyl vinyl ether, 1-vinyl-2-pyrrolidinone) to afford chroman derivatives, i.e. 2,3-dihydro-1H-naphtho[2,1-b]pyrans and 3,4-dihydro-2H-1-benzopyrans, respectively.

  研究表明，1-[δ-(苯并三唑-1-基)烷基]-2-萘酚和 2-[(苯并三唑-1-基)-甲基]苯酚在失去一分子苯并三唑后会生成邻醌甲酯，这些邻醌甲酯可与富含电子的烯烃（乙烯基乙醚、1-乙烯基-2-吡咯烷酮）作用生成铬烷衍生物，即 2,3-二氢-1H-萘并[2,1-b]吡喃和 3,4-二氢-2H-1-苯并吡喃。即 2,3-二氢-1H-萘并[2,1-b]吡喃和 3,4-二氢-2H-1-苯并吡喃。
• Visible light-induced C(sp³)–H azolation of ethers <i>via</i> radical-polar crossover
  作者：Cheng Huang、Yu-Shu Qin、Chen-Lu Wang、Peng Xiao、Sheng Tang、Hong-Jun Liu、Zhenhong Wei、Hu Cai

  DOI：10.1039/d3cc06210d

  日期：——

  We report a metal-free and photocatalyst-free strategy for C(sp³)–H azolation of ethers via a hydrogen-atom transfer and radical-polar crossover process.

  我们报告了一种通过氢原子转移和自由基-极性交叉过程实现醚的 C（sp3）-H 叠氮化的无金属、无光催化剂策略。
• Cross-Dehydrogenative Coupling of Azoles with α-C(sp³)–H of Ethers and Thioethers under Metal-Free Conditions: Functionalization of H–N Azoles via C–H Activation
  作者：Hariprasad Aruri、Umed Singh、Sumit Sharma、Satish Gudup、Mukesh Bhogal、Sanjay Kumar、Deepika Singh、Vivek K. Gupta、Rajni Kant、Ram A. Vishwakarma、Parvinder Pal Singh

  DOI：10.1021/jo502477r

  日期：2015.2.6

  A metal-free cross-dehydrogenative coupling method for the synthesis of N-substituted azoles has been developed. The TBAI/TBHP system catalyzed the coupling of azoles with ethers and thioethers via a-C(sp(3))H activation. Under the optimized conditions, a diverse range of un/substituted azoles such as 1H-benzimidazole, 9H-purine, 1H-benzotriazole, 1H-1,2,3-triazole, 1H-1,2,4-triazole, and 1H-pyrazole were successfully employed for coupling with various ethers and thioethers such as tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethyl ether, tetrahydrothiophene, and 1,3-dithiolane.