疊氮乙酸乙酯

化合物

疊氮乙酸乙酯是一種有機化合物,化學式為C4H7N3O2。它可以溴乙酸乙酯疊氮化鈉為原料反應製得。[1]它和苯乙炔在催化下反應,可以得到4-苯基-1H-1,2,3-三唑-1-乙酸乙酯;[3]它和乙醯腈加壓反應,可以得到5-乙醯基-1H-四唑-1-乙酸乙酯。[4]它在50%甲醇水溶液中用氫氧化鋰水解,再酸化後可以得到疊氮乙酸。[5]

疊氮乙酸乙酯
識別
CAS號 637-81-0  checkY
PubChem 69480
SMILES
 
  • CCOC(=O)CN=[N+]=[N-]
InChI
 
  • 1S/C4H7N3O2/c1-2-9-4(8)3-6-7-5/h2-3H2,1H3
InChIKey HVJJYOAPXBPQQV-UHFFFAOYSA-N
性質
化學式 C4H7N3O2
摩爾質量 129.12 g·mol−1
密度 1.1181 g·cm-3(25 °C)[1]
沸點 74—75 °C(347—348 K)(23 mmHg)[1]
164 °C(437 K)(760 mmHg)[2]
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

參考文獻

  1. ^ 1.0 1.1 1.2 Huber, W. Frederick. Mono-α-aminoacyl and Mono-α-dipeptide Triglycerides. Journal of the American Chemical Society (American Chemical Society (ACS)). 1955, 77 (1): 112–116. ISSN 0002-7863. doi:10.1021/ja01606a036. 
  2. ^ Swetha, M.; Ramana, P. Venkata; Shirodkar, S. G. Simple and Efficient Method for the Synthesis of Azides in Water-THF Solvent System. Organic Preparations and Procedures International (Informa UK Limited). 2011, 43 (4): 348–353. ISSN 0030-4948. doi:10.1080/00304948.2011.594002. 
  3. ^ Díaz Velázquez, Heriberto; Ruiz García, Yara; Vandichel, Matthias; Madder, Annemieke; Verpoort, Francis. Water-soluble NHC-Cu catalysts: applications in click chemistry, bioconjugation and mechanistic analysis. Org. Biomol. Chem. (Royal Society of Chemistry (RSC)). 2014, 12 (46): 9350–9356. ISSN 1477-0520. doi:10.1039/c4ob01350f. 
  4. ^ Zavarzin, I. V.; Zhulin, V. M.; Yarovenko, V. N.; Krayushkin, M. M. Synthesis of 5-acyltetrazoles under high pressure(俄文). Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1988. (5): 1168-1170
  5. ^ Valverde, Ibai E.; Bauman, Andreas; Kluba, Christiane A.; Vomstein, Sandra; Walter, Martin A.; Mindt, Thomas L. 1,2,3‐Triazoles as Amide Bond Mimics: Triazole Scan Yields Protease‐Resistant Peptidomimetics for Tumor Targeting. Angewandte Chemie International Edition (Wiley). 2013-07-05, 52 (34): 8957–8960. ISSN 1433-7851. doi:10.1002/anie.201303108.