4-(2-azidoethyl)benzene-1,2-diol | 1608889-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-azidoethyl)benzene-1,2-diol
• 英文别名: dopamine azide；4-(2-Azidoethyl)benzene-1,2-diol
• CAS: 1608889-96-8
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: UIDZXCNMEUJHNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-benzyl-2,2-dimethyl-3-(prop-2-ynyl)imidazolidin-4-one 、 4-(2-azidoethyl)benzene-1,2-diol 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以67%的产率得到(5S)-5-benzyl-3-[[1-[2-(3,4-dihydroxyphenyl)ethyl]triazol-4-yl]methyl]-2,2-dimethylimidazolidin-4-one
  参考文献：
  名称：

  Magnetoclick咪唑烷酮纳米催化剂用于不对称的1,3-偶极环加成反应

  摘要：

  AbstractA 1,3‐dipolar azide–alkyne cycloaddition has been used to prepare a magnetic nanoparticle immobilized MacMillan catalyst that catalyzes the enantioselective 1,3‐dipolar cycloaddition between nitrones and α,β‐unsaturated aldehydes. The catalyst can be recovered and recycled for five consecutive runs without any significant loss in yields and diastereo‐ and enantioselectivities of the isoxazolidines.magnified image

  DOI：

  10.1002/adsc.201300624
• 作为产物：
  描述：

  盐酸多巴胺 在 triflic azide 、 三乙胺 、 zinc(II) chloride 作用下， 以 水 、 乙腈 为溶剂， 以74%的产率得到4-(2-azidoethyl)benzene-1,2-diol
  参考文献：
  名称：

  Magnetoclick咪唑烷酮纳米催化剂用于不对称的1,3-偶极环加成反应

  摘要：

  AbstractA 1,3‐dipolar azide–alkyne cycloaddition has been used to prepare a magnetic nanoparticle immobilized MacMillan catalyst that catalyzes the enantioselective 1,3‐dipolar cycloaddition between nitrones and α,β‐unsaturated aldehydes. The catalyst can be recovered and recycled for five consecutive runs without any significant loss in yields and diastereo‐ and enantioselectivities of the isoxazolidines.magnified image

  DOI：

  10.1002/adsc.201300624

文献信息

• Conjugation of Hydroxytyrosol with Other Natural Phenolic Fragments: From Waste to Antioxidants and Antitumour Compounds
  作者：Erika Tassano、Angela Alama、Andrea Basso、Giancarlo Dondo、Andrea Galatini、Renata Riva、Luca Banfi

  DOI：10.1002/ejoc.201500931

  日期：2015.10

  Hydroxytyrosol, a natural polyphenol that can be extracted from olive mill waste waters, was converted into a series of more complex and lipophilic analogues by conjugation with other naturally derived (poly)phenolic fragments. Ether and triazole linkers were employed. A small library of compounds was prepared, stressing step economy and operational simplicity. Some of these substances were proven

  羟基酪醇是一种可以从橄榄厂废水中提取的天然多酚，通过与其他天然衍生的（多）酚类片段结合，转化为一系列更复杂和亲脂的类似物。使用醚和三唑接头。准备了一个小型化合物库，强调步骤经济和操作简单。在自由基清除试验以及对肿瘤细胞的细胞毒性试验中，这些物质中的一些被证明具有与母体羟基酪醇相同或优于母体羟基酪醇的活性。
• Highly Functionalized SWCNTs with a Dopamine Derivative as a Support for Pd Nanoparticles: A Recyclable Catalyst for the Reduction of Nitro Compounds and the Heck Reaction
  作者：Vincenzo Campisciano、Laura Valentino、Maria Laura Alfieri、Valeria La Parola、Alessandra Napolitano、Francesco Giacalone、Michelangelo Gruttadauria

  DOI：10.1002/chem.202301238

  日期：2023.10.18

  The [3+2] cycloaddition reaction of dopamine azide on SWCNTs in o-DCB at 160 °C gave a material with high degree of functionalization still maintaining π-network of SWCNTs. The presence of the catechol units was exploited to immobilize palladium nanoparticles. The hybrid material was used as a recyclable catalyst for the reduction of nitro compounds and the Heck reaction.

  多巴胺叠氮化物在邻二氯苯中于160℃下在单壁碳纳米管上发生[3+2]环加成反应，得到一种高度功能化的材料，同时仍保持单壁碳纳米管的π网络。利用儿茶酚单元的存在来固定钯纳米颗粒。该杂化材料被用作硝基化合物还原和赫克反应的可回收催化剂。
• [EN] APPLICATION OF FSO2N3 IN PREPARATION OF AZIDE<br/>[FR] UTILISATION DE FSO2N3 DANS LA PRÉPARATION D'AZIDE<br/>[ZH] FSO 2N 3在制备叠氮化合物中的应用
  申请人：SHANGHAI INSITITUTE OF ORGANIC CHEMISTRY CHINESE ACAD OF SCIENCES

  公开号：WO2019238057A1

  公开（公告）日：2019-12-19

  一种FSO2N3在制备叠氮化合物中的应用，使用FSO2N3进行重氮转移反应(diazo transfer)，可从一级胺基化合物(包括一级烷基胺类化合物(R-NH2)，(杂)芳基胺类化合物(Ar-NH2)或磺酰胺类化合物(RSO2NH2))快速、安全、高收率地制备对应的叠氮化合物(R-N3，Ar-N3或RSO2N3)；且操作简单、高效。
• A Magnetoclick Imidazolidinone Nanocatalyst for Asymmetric 1,3‐Dipolar Cycloadditions
  作者：Sreenivasarao Pagoti、Debasish Dutta、Jyotirmayee Dash

  DOI：10.1002/adsc.201300624

  日期：2013.12.16

  AbstractA 1,3‐dipolar azide–alkyne cycloaddition has been used to prepare a magnetic nanoparticle immobilized MacMillan catalyst that catalyzes the enantioselective 1,3‐dipolar cycloaddition between nitrones and α,β‐unsaturated aldehydes. The catalyst can be recovered and recycled for five consecutive runs without any significant loss in yields and diastereo‐ and enantioselectivities of the isoxazolidines.magnified image