(R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Base Information

• Chemical Name: (R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid
• CAS No.: 104974-44-9
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.23
• European Community (EC) Number: 634-643-9
• Nikkaji Number: J668.054B
• Mol file: 104974-44-9.mol

Synonyms:104974-44-9;(R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid;(R)-2-Aminotetralin-2-carboxylic acid;(2R)-2-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid;SCHEMBL199421;AKOS015908467;CS-0376373;2-Naphthalenecarboxylicacid,2-amino-1,2,3,4-tetrahydro-,(2R)-;(R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid, >=99.0% (HPLC)

Chemical Property of (R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Chemical Property:

• PSA: 63.32000
• LogP: 1.65770
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

(R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ≥99.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CC2=CC=CC=C21)(C(=O)O)N
• Isomeric SMILES: C1C[C@@](CC2=CC=CC=C21)(C(=O)O)N
• General Description: (S)-2-Amino-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (Atc) is a conformationally constrained phenylalanine analog used in opioid peptide design to study receptor selectivity and stereospecificity. When incorporated into deltorphin analogs, (S)-Atc maintains high δ-opioid receptor affinity and selectivity, with minimal disruption to the peptide backbone conformation. Unlike unconstrained Phe analogs, (S)-Atc exhibits reduced stereospecificity in binding, as both (R)- and (S)-isomers show similar potency. The constrained side chain of (S)-Atc adopts a trans conformation at χ₁ during δ-receptor interaction, supporting its role in stabilizing bioactive conformations. In cyclic opioid peptides, Atc substitution can shift receptor preference, though its effects depend on the peptide scaffold and ring size. Overall, (S)-Atc serves as a valuable tool for probing opioid receptor interactions and enhancing peptide stability.

Technology Process of (R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

There total 17 articles about (R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(S)-ethyl 2-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylate (1115955-17-3) → (S)-2-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (104974-44-9,74444-77-2)

Guidance literature:

(S)-ethyl 2-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylate; With lithium hydroxide monohydrate; In ethanol; water; at 25 ℃; for 48h;

With hydrogenchloride; In ethanol; water; pH=2; optical yield given as %ee;

DOI:10.1021/ol802325h

Reference yield: 97.0%

7,8-benzo-1,3-diazasprio[4.5]decane-2,4-dione (52094-70-9) → 2-amino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (6331-63-1,104974-44-9,104974-45-0,74444-77-2)

Guidance literature:

With barium dihydroxide; In water; ethylene glycol; for 27h; Heating;

DOI:10.1002/(SICI)1099-1344(199710)39:10<817::AID-JLCR28>3.0.CO;2-B

Reference yield: 96.0%

2-amino-2-(aminocarbonyl)-1,2,3,4-tetrahydronaphthalene (144800-66-8) → 2-amino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (6331-63-1,104974-44-9,104974-45-0,74444-77-2)

Guidance literature:

With hydrogenchloride; Heating;

DOI:10.1021/jm00020a021

upstream raw materials:

1,2,3,4-tetrahydronaphthalen-2-one

7,8-benzo-1,3-diazasprio[4.5]decane-2,4-dione

acide amino-2 chloro-6 tetrahydro-1,2,3,4 naphtoique-2

2-amino-2-(aminocarbonyl)-1,2,3,4-tetrahydronaphthalene

Downstream raw materials:

(R)-2-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

(S)-2-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

(R)-2-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid hydrochloride

N^2.2-<(R)-2-benzamido-1,2,3,4-tetrahydronaphthalene-2-carbonyl>-L-phenylalanyl-L-phenylalanine N^1.3,N^1.3-(tetramethylene)amide