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Cas Database |
| Name |
N-Benzyloxycarbonyl-L-proline |
EINECS | 214-557-4 |
| CAS No. | 1148-11-4 | Density | 1.309 g/cm3 |
| PSA | 66.84000 | LogP | 1.81010 |
| Solubility | N/A | Melting Point |
76-78 °C |
| Formula | C13H15NO4 | Boiling Point | 432.3 °C at 760 mmHg |
| Molecular Weight | 249.266 | Flash Point | 215.3 °C |
| Transport Information | N/A | Appearance | white to light yellow crystal powder |
| Safety | 22-24/25-36-26 | Risk Codes | 62-36/37/38-20/21/22 |
| Molecular Structure |
|
Hazard Symbols |
 Xn
|
| Synonyms |
1,2-Pyrrolidinedicarboxylicacid, 1-(phenylmethyl) ester, (S)-;1,2-Pyrrolidinedicarboxylic acid, 1-benzylester, L- (8CI);(2S)-1,2-Pyrrolidinedicarboxylic acid 1-(phenylmethyl) ester;(2S)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylic acid;(S)-1-(Benzyloxycarbonyl)pyrrolidine-2-carboxylicacid;1-(Benzyloxycarbonyl)-L-proline;1-Carbobenzoxy-L-proline;Benzyloxycarbonyl-L-proline;Carbobenzoxy-L-proline;Carbobenzoxy-S-proline;Carbobenzyloxy-L-proline;Cbz-L-Pro-OH;N-Benzyloxycarbonyl-(S)-proline;N-Carbobenzyloxy-(S)-proline;N-Cbz-L-proline;N-[(Phenylmethoxy)carbonyl]-L-proline; |
Article Data | 122 |
N-Benzyloxycarbonyl-L-proline Synthetic route
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water for 13.5h; Ambient temperature; | 100% |
| With sodium carbonate at 0 - 20℃; for 3h; | 100% |
| With sodium hydroxide at 0℃; for 0.166667h; | 97% |
- 124980-30-9
N-carbobenzoxy-L-proline phenylmethyl ester
- 1148-11-4
N-Benzyloxycarbonyl-L-proline
| Conditions | Yield |
|---|---|
| With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere; | 98% |
| With 1,4-diaza-bicyclo[2.2.2]octane; hydrogen; palladium on activated charcoal; ethylenediamine In methanol at 20℃; under 760 Torr; for 6h; Hydrogenolysis; | 76% |
| With dmap; hydrogen; palladium on activated charcoal; ethylenediamine In methanol at 20℃; for 3h; | 75% |
- 2133-40-6
L-proline methyl ester monohydrochloride
- 501-53-1
benzyl chloroformate
- 1148-11-4
N-Benzyloxycarbonyl-L-proline
| Conditions | Yield |
|---|---|
| With water; sodium hydroxide In toluene at 0 - 5℃; Large scale; | 94% |
| With sodium hydroxide In water at 0 - 5℃; Industrial scale; |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In sodium hydroxide; toluene | 98% |
| With hydrogenchloride In sodium hydroxide; toluene | 98% |
| With hydrogenchloride In sodium hydroxide; toluene | 98% |
| With sodium hydroxide In chloroform; water | 96% |
- 1148-11-4
N-Benzyloxycarbonyl-L-proline
| Conditions | Yield |
|---|---|
| With palladium diacetate; sodium hydride In N,N-dimethyl acetamide; mineral oil at 25℃; for 4h; Inert atmosphere; | 97% |
| Conditions | Yield |
|---|---|
| With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; sodium bromide In water; acetone at 20℃; for 24h; | 100% |
| With sodium chlorite; Me-AZADO+BF4- In acetonitrile at 25℃; for 1.5h; pH=6.7; aq. phosphate buffer; |
| Conditions | Yield |
|---|---|
| With sodium hydroxide at 0℃; | 95% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; sodium hydroxide; sodium methylate; triethylamine In methanol; water; N,N-dimethyl-formamide | 45.5% |
| Conditions | Yield |
|---|---|
| With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 20℃; for 16h; |
- 60-29-7
diethyl ether
- 99464-81-0
benzyl (1-chloroethyl) carbonate
- 147-85-3
L-proline
- 1148-11-4
N-Benzyloxycarbonyl-L-proline
| Conditions | Yield |
|---|---|
| In methanol; water; ethyl acetate; Petroleum ether | 88% |
N-Benzyloxycarbonyl-L-proline Specification
The IUPAC name of N-Carbobenzoxy-L-proline is 1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid . With the CAS registry number 1148-11-4, it is also named as 1-(Benzyloxycarbonyl)proline ; Benzyloxycarbonyl-L-proline ; Benzyloxycarbonylproline ; Carbobenzoxy-L-proline ; Carbobenzoxy-S-proline ; L-1,2-Pyrrolidinedicarboxylic acid 1-benzyl ester ; 1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester, (S)- (9CI) .
The N-Carbobenzoxy-L-proline is white to light yellow crystal powder which should be stored at the temperature of 2-8 °C. It is harmful by inhalation, in contact with skin and if swallowed. And it is irritating to eyes, respiratory system and skin. Risk of impaired fertility. So people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.17 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -0.35 ; (4)ACD/LogD (pH 7.4): -2.07 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 3.13 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 5 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 4 ; (12)Index of Refraction: 1.582 ; (13)Molar Refractivity: 63.55 cm3 ; (14)Molar Volume: 190.3 cm3 ; (15)Polarizability: 25.19×10-24 cm3 ; (16)Surface Tension: 58.5 dyne/cm ; (17)Enthalpy of Vaporization: 72.53 kJ/mol ; (18)Vapour Pressure: 3.06E-08 mmHg at 25°C ; (19)Rotatable Bond Count: 4 ; (20)Exact Mass: 249.100108 ; (21)MonoIsotopic Mass: 249.100108 ; (22)Topological Polar Surface Area: 66.8 ; (23)Heavy Atom Count: 18.
People can use the following data to convert to the molecule structure. SMILES: O=C(O)[C@@H]2N(C(=O)OCc1ccccc1)CCC2; InChI: InChI=1/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m1/s1.
The following is the toxicity data which has been tested.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravaginal | > 1gm/kg (1000mg/kg) | Journal of Pharmaceutical Sciences. Vol. 68, Pg. 696, 1979. |
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