116611-55-3

Basic information

• Product Name: (1S)-N-(tert-Butoxycarbonyl)-1-propyl-2-hydroxyethylamine
• Synonyms: (1S)-N-(tert-Butoxycarbonyl)-1-propyl-2-hydroxyethylamine;(S)-[1-(Hydroxymethyl)butyl]carbamic acid 1,1-dimethylethyl ester;[(1S)-1-(Hydroxymethyl)butyl]carbamic acid 1,1-dimethylethyl ester;N-[(1S)-1-(Hydroxymethyl)butyl]carbamic acid tert-butyl ester;CarbaMic acid, N-[(1S)-1-(hydroxyMethyl)butyl]-, 1,1-diMethylethyl ester;(S)-2-(Boc-amino)-1-pentanol
• CAS NO: 116611-55-3
• Molecular Formula: C₁₀H₂₁NO₃
• Molecular Weight: 203.27864
• Mol File: 116611-55-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 43-45℃
• Boiling Point: 309℃
• Flash Point: 141℃
• Appearance: /
• Density: 0.997
• PKA: 12.11±0.46(Predicted)
• CAS DataBase Reference: (1S)-N-(tert-Butoxycarbonyl)-1-propyl-2-hydroxyethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-N-(tert-Butoxycarbonyl)-1-propyl-2-hydroxyethylamine(116611-55-3)
• EPA Substance Registry System: (1S)-N-(tert-Butoxycarbonyl)-1-propyl-2-hydroxyethylamine(116611-55-3)

Safety Data

• Hazardous Substances Data: 116611-55-3(Hazardous Substances Data)

Usage

General Description

(1S)-N-(tert-Butoxycarbonyl)-1-propyl-2-hydroxyethylamine is a chiral compound with a chemical formula of C11H23NO4. It is a tertiary amine with a hydroxyethyl and a propyl group attached to the nitrogen atom. The tert-Butoxycarbonyl (t-BOC) group is a protecting group commonly used in organic synthesis to protect amines from unwanted reactions. (1S)-N-(tert-Butoxycarbonyl)-1-propyl-2-hydroxyethylamine is used in organic chemistry as a building block for the synthesis of various pharmaceuticals and bioactive compounds. The chiral nature of this compound makes it important for the synthesis of enantiomerically pure molecules, which is critical in the pharmaceutical industry for the development of safe and effective drugs.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 22724-81-8 L-norvalinol 
• 2013-12-9 D-norvaline 
• 116611-52-0 [(S)-2-Benzenesulfonyl-1-(tetrahydro-pyran-2-yloxymethyl)-butyl]-carbamic acid tert-butyl ester 
• 116611-50-8 ((S)-2-Benzenesulfonyl-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester 
• 116611-47-3 Toluene-4-sulfonic acid (S)-2-tert-butoxycarbonylamino-3-(tetrahydro-pyran-2-yloxy)-propyl ester 
• 116611-48-4 [(S)-2-Phenylsulfanyl-1-(tetrahydro-pyran-2-yloxymethyl)-ethyl]-carbamic acid tert-butyl ester 
• 116611-63-3 methyl N-(tert-butoxycarbonyl)-O-(tetrahydro-2H-pyran-2-yl)-L-serinate 
• 116611-46-2 tert-butyl [(2R)-1-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl]carbamate 
• 116696-85-6 (2S)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 116611-49-5 ((S)-1-Hydroxymethyl-2-phenylsulfanyl-ethyl)-carbamic acid tert-butyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 116611-61-1 ((S)-2-Benzenesulfonyl-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester 
• 116611-52-0 [(R)-2-Benzenesulfonyl-1-(tetrahydro-pyran-2-yloxymethyl)-butyl]-carbamic acid tert-butyl ester 

Downstream Products

• 53308-95-5 N-tert-butoxycarbonyl-L-norvaline 
• 57521-85-4 N-tert-butoxycarbonyl-D-norvaline 
• 1196038-35-3 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid {(S)-2-[3-(4-methoxy-phenyl)-propylamino]-pentyl}-amide 
• 160801-74-1 (2S)-2-(1,1-dimethylethoxycarbonylamino)pentanal 
• 757976-38-8 tert-butyl ((1S)-1-{[(4-methoxyphenyl)amino]methyl}butyl)carbamate 
• 1196793-29-9 (S,E)-tert-butyl 1-(3,5-diamino-6-chloropyrazin-2-yl)-7-(3-(4-methoxyphenyl)propyl)-10,10-dimethyl-1,8-dioxo-4-propyl-9-oxa-2,5,7-triazaundecan-6-ylidenecarbamate 
• 1201179-46-5 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid {(S)-2-[3-(4-methoxy-phenyl)-propylamino]-pentyl}-amide hydrochloride 
• 1196038-40-0 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-{N'-[3-(4-methoxy-phenyl)-propyl]-guanidino}-pentyl)-amide 
• 246256-62-2 (1-propyl-but-3-enyl)-carbamic acid tert-butyl ester 
• 757976-39-9 N¹-(4-methoxy-phenyl)-pentane-1,2-diamine 

Relevant articles and documents

A highly efficient synthesis of (S)-(+)-N-Boc-coniine using ring- closing olefin metathesis (RCM)

Optically active (S)-(+)-coniine as an N-Boc protected form was concisely prepared starting from an amino acid, L-norvaline. The key step involved a ring-closing olefin metathesis (RCM) of the dialkenyl compound 6 to give the corresponding cyclic olefin 8 in an essentially quantitative yield.

Design, synthesis, and structure-activity relationship studies of L-amino alcohol derivatives as broad-spectrum antifungal agents

To discover broad spectrum antifungal agents, two strategies were applied, and a novel class of L-amino alcohol derivatives were designed and synthesized. 3-F substituted compounds 14i, 14n, 14s and 14v exhibited excellent antifungal activities with broad antifungal spectra against C. albicans and C. tropicalis, with MIC values in the range of 0.03–0.06 μg/mL, and against A. fumigatus and C. neoformans, with MIC values in the range of 1–2 μg/mL. Notably, Compounds 14i, 14n, 14s and 14v also displayed moderate activities against fluconazole-resistance strains 17# and CaR that were isolated from AIDS patients. Moreover, only compounds in the S-configuration showed antifungal activity. Preliminary mechanistic studies showed that the potent antifungal activity of compound 14v stemmed from inhibition of C. albicans CYP51. Compounds 14n and 14v were almost nontoxic to mammalian A549 cells, and their stability in human plasma was excellent.

Synthesis of imidacloprid derivatives with a chiral alkylated imidazolidine ring and evaluation of their insecticidal activity and affinity to the nicotinic acetylcholine receptor

A series of imidacloprid (IMI) derivatives with an alkylated imidazolidine ring were asymmetrically synthesized to evaluate their insecticidal activity against adult female housefly, Musca domestica, and affinity to the nicotinic acetylcholine receptor of the flies. The bulkier the alkyl group, the lower was the receptor affinity, but the derivatives methylated and ethylated at the R-5-position of the imidazolidine ring were equipotent to the unsubstituted compound. Quantitative structure-activity relationship (QSAR) analysis of the receptor affinity demonstrated that the introduction of a substituent into the imidazolidine ring was fundamentally disadvantageous, but the introduction of a substituent at the R-5-position was permissible in the case of its small size. The binding model of the synthesized derivatives with the receptor supported the QSAR analysis, indicating the existence of space for a short alkyl group around the R-5-position in the ligand-binding site. In addition, positive correlation was observed between the insecticidal activity and receptor affinity, suggesting that the receptor affinity was the primary factor in influencing the insecticidal activity even if the imidazolidine ring was modified.