二炭酸ジ-tert-ブチル 化学特性,用途語,生産方法
外観
白色/無色～うすい黄色粉末～塊～透明液体
外観
無色～ほとんど無色透明液体
溶解性
アセトンに極めて溶けやすく、水に徐々に分解する。
用途
2-ピペリドンからの6-アセチル-1,2,3,4-テトラヒドロピリジンの合成は二炭酸ジ-tert-ブチルを用いたBoc保護を経ることによって達成された[5]。最初の反応では、アセトニトリル中、二炭酸ジ-tert-ブチルとDMAPを用いて第二級アミンをBocカルバメートとする。
用途
BOC保護アミノ酸合成用。
使用
Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. It plays an important role in the preparation of 6-acetyl-1,2,3,4-tetrahydropyridine by reacting with 2-piperidone. It serves as a protecting group used in solid phase peptide synthesis.
主な応用
Di-tert-butyl dicarbonate has the following uses:
(1) As part of a series of bovine plasma amine oxidase inactivators. Aminomethylenes were prepared by the reaction of Boc propargylamine with formaldehyde, diisopropylamine and copper bromide.
(2) It can be used as a general purpose carboxylation reagent. Carbon nucleophiles generated by a non-nucleophilic base (LDA) were effectively trapped with di-tert-butyl dicarbonate (Boc-anhydride) to provide the corresponding tert-butyl aryl acetates, di-tert-butyl aryl malonates, unsymmetrical aryl malonates and tert-butyl benzoates in high yields.
(3) Alcohols as Boc derivatives were catalytically protected by Lewis acids. Reagents for the introduction of Boc protecting groups.
(4) Reagents for the preparation of Boc-protected amines. Tri-tert-butoxycarbonyl-protected hydrazines prepare Fmoc esters in chromogenic reagents for monitoring solid-phase aldehydes.
定義
ChEBI: Di-tert-butyl dicarbonate is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid.
製造方法
The preparation of Di-tert-butyl dicarbonate is as follows:To a monoester sodium salt solution were added 2g of N, N-dimethylformamide, 1g of pyridine, 1g of triethylamine,Cooling to -5~0°C, 60g diphosgene was slowly added dropwise within 1.5h dropwise addition was complete, warmed to room temperature (25°C), incubated for 2h, the reaction was allowed to stand after filtration, washing organic solution. Dried with anhydrous magnesium sulfate, the solvent was distilled off at atmospheric pressure to give crude product 65~70g. After cooling and crystallization, 57-60g of di-tert-butyl dicarbonate were obtained in a yield of 60-63%.
反応性
The reaction of substituted anilines with Boc2O in the presence of a stoichiometric amount of 4-dimethylaminopyridine (DMAP) in an inert solvent (acetonitrile, dichloromethane, ethyl acetate, tetrahydrofuran, toluene) at room temperature leads to aryl isocyanates in almost quantitative yields within 10 min.
Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. Their reactions with amines and alcohols
一般的な説明
Di-
tert-butyl dicarbonate (Boc
2O) is a reagent mainly used for the introduction of the Boc protecting group to amine functionalities. It is also used as a dehydrating agent in some organic reactions, particularly with carboxylic acids, certain hydroxyl groups, or with primary nitroalkanes.
危険性
An irritant that may cause serious eye injury; May cause skin sensitization; Highly toxic by inhalation
純化方法
Melt the ester by heating at ~35o, and distil it in a vacuum. If IR and NMR ( 1810m 1765 cm-1 , in CCl4 1.50 singlet) suggest very max impure, then wash with an equal volume of H2O containing citric acid to make the aqueous layer slightly acidic, collect the organic layer and dry it over anhydrous MgSO4 and distil it in a vacuum. [Pope et al. Org Synth 57 45 1977, Keller et al. Org Synth 63 160 1985, Grehn et al. Angew Chem 97 519 1985.] FLAMMABLE.
二炭酸ジ-tert-ブチル 上流と下流の製品情報
原材料
準備製品