“2,2,2-Trichloroethoxycarbonyl chloride”的意思、由来-开放百科全书

词条

2,2,2-Trichloroethoxycarbonyl chloride

释义

Amine protection – 2,2,2-Trichloroethoxycarbonyl (Troc)
Most common amine protection methods
References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477198803
| Reference = ^[1]
| ImageFile =2,2,2-Trichlorethoxycarbonyl chloride.svg
| ImageName = Skeletal formula of 2,2,2-Trichlorethoxycarbonyl chloride
| ImageFile1 =2,2,2-Trichlorethoxycarbonyl chloride-3D.png
| ImageName1 = Ball-and-stick model of the 2,2,2-Trichlorethoxycarbonyl chloride molecule
| PIN = 2,2,2-Trichloroethyl carbonochloridate
| OtherNames = 2,2,2-Trichlorethoxycarbonyl chloride
Trichloroethyl chloroformate
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 78534
| InChI = 1/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2
| InChIKey = LJCZNYWLQZZIOS-UHFFFAOYAA
| SMILES1 = ClC(Cl)(Cl)COC(Cl)=O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LJCZNYWLQZZIOS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 17341-93-4
| PubChem = 87063
| SMILES =O=C(OCC(Cl)(Cl)Cl)Cl
|Section2={{Chembox Properties
| C=3 | H=2 | Cl=4 | O=2
| Density =1.539 g/cm³
| MeltingPtC = 0
| MeltingPt_notes =
| BoilingPtC = 171 to 172
| BoilingPt_notes =
}}
|Section3={{Chembox Hazards
| EUClass =Toxic (T), Corrosive (C)
| RPhrases ={{R23}}, {{R34}}
| SPhrases ={{S26}}, {{S36/37/39}}
}}

Trichloroethyl chloroformate is used in organic synthesis for the introduction of the trichloroethyl chloroformate (Troc) protecting group for amines, thiols and alcohols. It readily cleaves vs other carbamates and can be used in an overall protecting group strategy.

The troc group is traditionally removed via Zn insertion in the presence of acetic acid, resulting in elimination and decarboxylation.

Amine protection – 2,2,2-Trichloroethoxycarbonyl (Troc)

{{clear-left}}

2,2,2-Trichloroethoxycarbonyl (Troc) group is largely used as a protecting group for amines in organic synthesis.

Most common amine protection methods

2,2,2-Trichloroethyl chloroformate, pyridine or aqueous sodium hydroxide at ambient temperature^[2]

{{clear-left}}

Electrolysis

{{clear-left}}

Deprotection using zinc metal

{{clear-left}}

References

1. ^2,2,2-Trichloroethyl chloroformate at Sigma-Aldrich
2. ^{{Cite journal|last=Marullo|first=N. P.|last2=Wagener|first2=E. H.|date=1969-01-01|title=Structural organic chemistry by nmr. III. Isomerization of compounds containing the carbon-nitrogen double bond|url=http://www.sciencedirect.com/science/article/pii/S004040390188566X|journal=Tetrahedron Letters|volume=10|issue=30|pages=2555–2558|doi=10.1016/S0040-4039(01)88566-X}}

3 : Chloroformates|Protecting groups|Reagents for organic chemistry

随便看

开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。