氯甲酸-9-芴甲酯

氯甲酸-9-芴甲酯[1]
IUPAC名
Chloroformic acid 9H-fluoren-9-ylmethyl ester
别名 9-芴甲氧羰酰氯；Fmoc-Cl
识别
CAS号 28920-43-6  checkY
PubChem 34367
ChemSpider 31647
SMILES
 
  • ClC(=O)OCC3c1ccccc1c2c3cccc2
InChI
 
  • 1/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2
InChIKey IRXSLJNXXZKURP-UHFFFAOYAT
性质
化学式 C15H11ClO2
摩尔质量 258.7 g·mol−1
熔点 62-64 °C
危险性
警示术语 R：R34
安全术语 S：S26 S36/37/39 S45
欧盟分类 Corrosive (C)
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

氯甲酸-9-芴甲酯（FMOC-Cl）是9-芴甲醇的氯甲酸酯。它用於使芴甲氧羰基(FMOC group)形成芴甲氧羰基氨基甲酸酯FMOC carbamate。

製備

氯甲酸-9-芴甲酯可以由9-芴甲醇和碳醯氯反应製備：[2]

反應

FMOC carbamate通常作為胺的保護基。例如:Fmoc-Cl的Fmoc基團會與胺基作用。[3]

Scheme showing addition of an Fmoc group to an amino acid

其他常見製備芴甲氧羰基(Fmox group)的方法是透過9 - 芴基甲基琥珀酰亞胺基碳酸酯 9-fluorenylmethyl succinimidyl carbonate (FMOC-OSu)，本身由Fmoc-Cl與雙環己基銨鹽(dicyclohexylammonium)中的N-羥基琥珀酰亞胺 (N-hydroxysuccinimide)反應獲得。[4]

Mechanism of the deprotection of the Fmoc group with piperidine.

在piperidine溶液中，會被鹼分離。 Fmoc保護基大量使用在胜肽鍵的合成法中，保護基可以在piperidine溶液中被去除，因此不會干擾胜肽鏈與樹脂之間的酸性連接物 此外Fmoc具有強螢光性，可以與不對UV反應的化合物進行連結，得到帶有Fmoc團的衍生物，該衍生物可以應用於反相液相層析析。使用FMOC-Cl分析，必須要先去除額外的荧光，因此不適合用於層析法

參考

  1. ^ Fmoc chloride （页面存档备份，存于互联网档案馆） at Sigma-Aldrich
  2. ^ Carpino, Louis A.; Han, Grace Y. 9-Fluorenylmethoxycarbonyl amino-protecting group. The Journal of Organic Chemistry. 1972, 37 (22): 3404. doi:10.1021/jo00795a005. 
  3. ^ Yamada, Kazuhiko; Hashizume, Daisuke; Shimizu, Tadashi; Ohki, Shinobu; Yokoyama, Shigeyuki. A solid-state 17O NMR, X-ray, and quantum chemical study of N-α-Fmoc-protected amino acids. Journal of Molecular Structure. 2008, 888: 187. doi:10.1016/j.molstruc.2007.11.059. 
  4. ^ Paquet, A. Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates. Canadian Journal of Chemistry. 1982, 60 (8): 976. doi:10.1139/v82-146. （原始内容存档于2012-07-26）. 

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