L-(−)-α-Amino-ε-caprolactam hydrochloride

Name: <SC>L</SC>-(−)-α-Amino-ε-caprolactam hydrochloride
Brand: ALDRICH
Price: 186 USD

≥97.0% (AT)

Synonym(s):

(S)-3-Amino-hexahydro-2-azepinone hydrochloride, L-Lysine lactam hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₆H₁₂N₂O · HCl

CAS Number:

26081-07-2

Molecular Weight:

164.63

Beilstein/REAXYS Number:

4820243

MDL number:

MFCD02683418

UNSPSC Code:

12352005

PubChem Substance ID:

57647925

NACRES:

NA.22

Key Documents

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Quality Level

100

assay

≥97.0% (AT)

form

solid

optical activity

[α]20/D −27±2°, c = 1% in H₂O

optical purity

enantiomeric ratio: ≥99:1 (HPLC)

storage temp.

2-8°C

SMILES string

Cl[H].N[C@H]1CCCCNC1=O

InChI

1S/C6H12N2O.ClH/c7-5-3-1-2-4-8-6(5)9;/h5H,1-4,7H2,(H,8,9);1H/t5-;/m0./s1

InChI key

LWXJCGXAYXXXRU-JEDNCBNOSA-N

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Catalysts

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Chiral Catalysts & Ligands

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This Item	50070	90182	62880
Sigma-Aldrich 21612 L-(−)-α-Amino-ε-caprolactam hydrochloride	Sigma-Aldrich 50070 Glycinamide hydrochloride	Sigma-Aldrich 90182 N_α-Tosyl-L-lysine chloromethyl ketone hydrochloride	Sigma-Aldrich 62880 L-Lysine ethyl ester dihydrochloride
assay ≥97.0% (AT)	assay ≥99.0% (AT)	assay ≥99.0% (AT)	assay ≥99.0% (AT)
Quality Level 100	Quality Level 200	Quality Level 100	Quality Level 100
form solid	form solid	form powder or crystals	form solid
storage temp. 2-8°C	storage temp. -	storage temp. −20°C	storage temp. -
optical activity [α]20/D −27±2°, c = 1% in H₂O	optical activity -	optical activity [α]20/D −7.8±0.5°, c = 2% in H₂O	optical activity [α]20/D +10±1°, c = 2% in H₂O
optical purity enantiomeric ratio: ≥99:1 (HPLC)	optical purity -	optical purity -	optical purity -

Application

L-(−)-α-Amino-ε-caprolactam hydrochloride can be used to introduce caprolactam moiety during the total synthesis of bengamides, which are bioactive compounds naturally found in marine sponges.[1][2][3]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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A diversity-oriented synthetic approach to bengamides

Sarabia F and S'anchez-Ruiz A

Tetrahedron Letters, 46(7), 1131-1135 (2005)

Total synthesis of bengamide E and analogues by modification at C-2 and at terminal olefinic positions

Sarabia F and S'anchez-Ruiz A

The Journal of Organic Chemistry, 70(23), 9514-9520 (2005)

Total synthesis of bengamide E

Liu W, et al.

Tetrahedron Letters, 43(8), 1373-1375 (2002)

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L-(−)-α-Amino-ε-caprolactam hydrochloride