| Identification | Back Directory | [Name]
TERT-BUTYL N,N-DIALLYLCARBAMATE | [CAS]
151259-38-0 | [Synonyms]
N-BOC-DIALLYLAMINE
tert-Butyl diallylcarbamate
TERT-BUTYL N,N-DIALLYLCARBAMATE
ert-butylN,N-bis(prop-2-enyl)carbamate
tert-butyl N,N-bis(prop-2-enyl)carbamate
N,N-bis(prop-2-enyl)carbamic acid tert-butyl ester
TERT-BUTYL N,N-DIALLYLCARBAMATE ISO 9001：2015 REACH
Carbamic acid, N,N-di-2-propen-1-yl-, 1,1-dimethylethyl ester | [Molecular Formula]
C11H19NO2 | [MDL Number]
MFCD01321306 | [MOL File]
151259-38-0.mol | [Molecular Weight]
197.27 |
| Chemical Properties | Back Directory | [Boiling point ]
75 °C/1.5 mmHg (lit.) | [density ]
0.914 g/mL at 25 °C (lit.) | [refractive index ]
n20/D 1.442(lit.) | [Fp ]
81 °C | [storage temp. ]
2-8°C, stored under nitrogen | [pka]
-1.46±0.70(Predicted) | [Appearance]
Colorless to light yellow Liquid | [InChI]
1S/C11H19NO2/c1-6-8-12(9-7-2)10(13)14-11(3,4)5/h6-7H,1-2,8-9H2,3-5H3 | [InChIKey]
RRIPHUBKNVVTBM-UHFFFAOYSA-N | [SMILES]
CC(C)(C)OC(=O)N(CC=C)CC=C |
| Hazard Information | Back Directory | [Uses]
tert-Butyl N,N-diallylcarbamate may be used in the synthesis of heterocyclic compounds. | [General Description]
tert-Butyl N,N-diallylcarbamate is a protected amine. Ring-closing metathesis (RCM) reactions of tert-butyl N,N-diallylcarbamate in the presence of Hoveyda-Grubbs type catalyst supported on mesoporous molecular sieves have been reported. | [Synthesis]
Example 5: (±)-trans-1-[(9-deaza-adenin-9-yl)methyl]-3-hydroxy-4-vinylpyrrolidine (1. X=vinyl, A=CH, B=NH, D=H);
Example 5.1: tert-butyl diallylcarbamate (7);
Di-tert-butyl dicarbonate (42.2 g, 193 mmol) was added batchwise to a solution of diallylamine (2) (20 mL, 162 mmol) in methanol (500 mL) at 0°C. After addition, the reaction mixture was gradually warmed to room temperature with continuous stirring for 1 hour. Subsequently, the reaction mixture was concentrated by distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate gradient elution, 0 to 50% ethyl acetate) to afford the target product tert-butyl diallylcarbamate 7 as a colorless oil (31.9 g, 99% yield). (Org. Biomol. Chem. 2004, 2, 2418-2420). | [References]
[1] Patent: WO2011/8110, 2011, A1. Location in patent: Page/Page column 41-42
[2] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8283 - 8286
[3] Synthesis, 2001, # 1, p. 46 - 48
[4] Synthesis, 2004, # 14, p. 2367 - 2375
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2016, vol. 71, # 6, p. 633 - 641 |
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