1-乙基-(3-二甲基氨基丙基)碳二亚胺

1-乙基-(3-二甲基氨基丙基)碳二亚胺
IUPAC名
3-[(Ethylimino)methylidene]amino-N,N-dimethylpropan-1-amine
识别
CAS号 1892-57-5  checkY
PubChem 15908
ChemSpider 15119
SMILES
 
  • N(=C=N\CCCN(C)C)\CC
InChI
 
  • 1/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3
InChIKey LMDZBCPBFSXMTL-UHFFFAOYAH
性质
化学式 C8H17N3
摩尔质量 155.24 g·mol−1
危险性
MSDS External MSDS (HCl salt)
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。
提示：此条目的主题不是內分泌干擾素。

1-乙基-3-(3-二甲基氨基丙基)碳二亚胺（亦稱为EDC、EDAC或EDCI）是一种水溶性碳二亚胺，常制成盐酸盐之形式。其pH范围通常在4.0-6.0。EDC常在伯胺制备酰氨时作为羧基活化剂。EDC还可用于活化磷酸基团。这种碳二亚胺通常用于肽的合成；蛋白质和核酸的交联以及制备免疫偶联物。EDC常与N-羟基丁二酰亚胺（NHS）或磺化－NHS搭配使用从而增加偶联反应的效率。

有机化学中，EDC还常与4-二甲氨基吡啶（DMAP）搭配使用作为羧酸和醇的酯化试剂，稱為施特格利希酯化反应。

制备

EDC为商业可售试剂，可通过乙基异氰酸酯和N,N-二甲基丙烷-1,3-二胺反应得脲，而后继续脱水制得：[1]

外部链接

参考文献

  1. ^ Sheehan, John; Cruickshank, Philip; Boshart, Gregory. A Convenient Synthesis of Water-Soluble Carbodiimides. J. Org. Chem. 1961, 26: 2525. doi:10.1021/jo01351a600. 

延伸阅读

  • López-Alonso, JP; Diez-Garcia, F; Font, J; Ribó, M; Vilanova, M; Scholtz, JM; González, C; Vottariello, F; Gotte, G; Libonati, M; Laurents, DV. Carbodiimide EDC Induces Cross-Links That Stabilize RNase A C-dimer against Dissociation: EDC Adducts Can Affect Protein Net Charge, Conformation and Activity. Bioconjug Chem. 2009, 20: 1459. doi:10.1021/bc9001486. 
  • Nakajima, N; Ikada, Y. Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media. Bioconjug Chem. 1995, 6: 123. doi:10.1021/bc00031a015. 
  • Skotnicki, S; Kearney, RM; Smith, AL. Synthesis of secorapamycin esters and amides. Tetrahedron Lett. 1994, 35: 197. doi:10.1016/S0040-4039(00)76509-9. 

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