60256-21-5

Basic information

• Product Name: ADAMANTAN-1-YL-AMINO-ACETIC ACID
• Synonyms: IFLAB-BB F1913-0001;AKOS BC-1228;ADAMANTAN-1-YL-AMINO-ACETIC ACID;Albb-007402;2-(1-Adamantyl)glycine;alpha-Aminotricyclo[3.3.1.13,7]decane-1-acetic acid;2-(AdaMantan-1-yl)-2-aMinoacetic acid;1-adamantyl(amino)acetic acid hydrochloride
• CAS NO: 60256-21-5
• Molecular Formula: C₁₂H₁₉NO₂
• Molecular Weight: 209.28
• Mol File: 60256-21-5.mol

Chemical Properties

• Boiling Point: 355.646 °C at 760 mmHg
• Flash Point: 168.889 °C
• Appearance: /
• Density: 1.244
• Vapor Pressure: 5.12E-06mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: 2-8°C(protect from light)
• PKA: 2?+-.0.10(Predicted)
• CAS DataBase Reference: ADAMANTAN-1-YL-AMINO-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ADAMANTAN-1-YL-AMINO-ACETIC ACID(60256-21-5)
• EPA Substance Registry System: ADAMANTAN-1-YL-AMINO-ACETIC ACID(60256-21-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 60256-21-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ADAMANTAN-1-YL-AMINO-ACETIC ACID is used as a potential pharmaceutical agent for its unique structural properties that may contribute to the development of new drugs. Its adamantane group's stability and the amine functionality of the amino-acetic acid could be leveraged to enhance drug delivery, target specific biological pathways, or improve the pharmacokinetic profile of medications.
Used in Materials Science:
In the field of materials science, ADAMANTAN-1-YL-AMINO-ACETIC ACID is utilized for its potential to contribute to the creation of novel materials with enhanced properties. The adamantane core's robustness and the compound's chemical versatility may facilitate the design of advanced materials with applications in coatings, adhesives, or other industrial uses.
Used in Organic Chemistry:
ADAMANTAN-1-YL-AMINO-ACETIC ACID serves as a building block or intermediate in organic synthesis. Its unique structure allows it to be a valuable component in the synthesis of complex organic molecules, potentially leading to the discovery of new chemical entities with specific applications in various industries.

InChI:InChI=1/C12H19NO2/c13-10(11(14)15)12-4-7-1-8(5-12)3-9(2-7)6-12/h7-10H,1-6,13H2,(H,14,15)

Upstream product

• 1660-04-4 1-acetyladamantane 
• 16091-98-8 oxo-tricyclo[3.3.1.1^3,7]decan-1-yl-acetic acid 
• 828-51-3 1-Adamantanecarboxylic acid 
• 16091-97-7 1-adamantyl-2-hydroxyiminoacetic acid 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 102572-74-7 R-methyl ester of amino-(1-adamantanyl)acetic acid 
• 98398-65-3 2-bromoadamantaneacetyl chloride 
• 82650-30-4 adamantan-1-yliodoacetic acid 
• 59768-70-6 2-(1-adamantyl)-2-bromoacetic acid 
• 1373751-77-9 D-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine 
• 328969-77-3 (S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 
• 895167-07-4 adamantan-1-yl-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-acetic acid 
• 895166-80-0 (R)-Adamantan-1-yl-[(S)-2-amino-3-(4-hydroxy-phenyl)-propionylamino]-acetic acid 
• 98398-64-2 Adamantan-1-yl-iodo-acetyl chloride 

Downstream Products

• 328969-74-0 rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 
• 709031-29-8 3-hydroxy-1-adamantyl-glycine 
• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 

Relevant articles and documents

A convenient method for the synthesis of (S)-N-boc-3- hydroxyadamantylglycine: A key intermediate of saxagliptin

(S)-N-Boc-3-Hydroxyadamantylglycine is a key intermediate of saxagliptin. It was synthesized from 1- adamantanecarboxylic acid to afford 1-acetyladamantane (2), which was converted into 2-(1-adamantyl)-2-oxoacetic acid (3) through oxidation, and then into 1-adamantyl-2-hydroxyimino acetic acid (4) followed by treatment of hydroxylamine hydrochloride, then 4 was reducted and Boc-protected to give N-Boc-adamantylglycine (5), which was oxidized with KMnO4 and treated with a chiral base. Utilizing this route, (S)-N-Boc-3- Hydroxyadamantylglycine was prepared. This work is to elaborate a convenient route to synthesize (S)-N-Boc-3-Hydroxyadamantylglycine and provide a new idea for the synthesis of saxagliptin.

Synthesis and immunostimulating properties of novel adamant-1-yl tripeptides

The aim of this work was to prepare L- and D-(adamant-1-yl)-Gly-L-Ala-D- isoGln peptides in order to study their adjuvant (immunostimulating) activities. Adjuvant activity of adamant-1-yl tripeptides was tested in the mouse model using ovalbumin as an ant

PROCESS FOR THE REDUCTIVE AMINATION OF α-KETO CARBOXYLIC ACIDS

The invention refers to a process for the reductive amination of α-keto carboxylic acids catalyzed by transition metal containing compounds.

Tumor-cell-targeted methionine-enkephalin analogues containing unnatural amino acids: Design, synthesis, and in vitro antitumor activity

A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma (HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested by the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-Gly-Gly-Phe-Met, or opioid growth factor, OGF), and its shorter N-terminal fragments. Peptide analogues containing Cαα-dialkylated glycine (Aaa1, 1) or Cα-alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R,S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.

Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: A combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution

Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1.

α-AMINO ACIDS IN THE ADAMANTANE SERIES. I. SYNTHESIS AND ENANTIOMERIC RESOLUTION OF 1-ADAMANTYLGLYCINE AND β-(1-ADAMANTYL)ALANINE

1-Adamantylglycine and β-(1-adamantyl)alanine have been synthesized via the amination of α-haloacids.Enantiomeric resolution of these compounds was achieved by separation of the diastereomeric salts formed between their methyl esters and d-dibenzoyltartaric acid as well as with d-camphor-10-sulfonic acid.In order to determine the absolute configurations of these amino acids, they were converted to Schiff bases and diastereomeric tetradentate Ni2+ complexes were synthesized from these derivatives.