139545-04-3

Basic information

• Product Name: (2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid
• Synonyms: (2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid
• CAS NO: 139545-04-3
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.34
• Mol File: 139545-04-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 489.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.141±0.06 g/cm3(Predicted)
• PKA: 4.48±0.10(Predicted)
• CAS DataBase Reference: (2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid(139545-04-3)
• EPA Substance Registry System: (2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid(139545-04-3)

Safety Data

• Hazardous Substances Data: 139545-04-3(Hazardous Substances Data)

Usage

Description

(2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid is an amino acid derivative with the molecular formula C16H21NO4. It features a tert-butoxycarbonyl (Boc) protecting group attached to the amino group, a phenyl group, and a pentenoic acid group, which together form a conjugated system of a carbon-carbon double bond and a carboxylic acid group. (2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid is widely used in organic synthesis as a versatile building block for the preparation of various compounds, including pharmaceuticals and biologically active molecules. The Boc protecting group can be removed under acidic conditions, enabling the functionalization of the amino group and its incorporation into larger molecules.

Uses

Used in Pharmaceutical Industry:
(2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid is used as a building block for the synthesis of pharmaceuticals and biologically active molecules. Its unique structure, including the phenyl group and the pentenoic acid group, allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid serves as a versatile intermediate for the preparation of various organic compounds. The presence of the Boc protecting group allows for selective deprotection and functionalization of the amino group, facilitating the synthesis of complex molecules with specific properties and functions.
Used in Research and Development:
(2E)-4-[(tert-Butoxycarbonyl)amino]-5-phenyl-2-pentenoic acid is also utilized in research and development for the exploration of new chemical reactions and the discovery of novel compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science. Its unique structural features make it an attractive candidate for studying new synthetic methodologies and reaction mechanisms.

Upstream product

• 116246-06-1 (E)-(S)-4-tert-Butoxycarbonylamino-5-phenyl-pent-2-enoic acid ethyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 99298-05-2 (E)-(S)-4-tert-butoxycarbonylamino-5-phenyl-pent-2-enoic acid methyl ester 
• 124818-94-6 ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 72155-45-4 Boc-L-phenylalaninal 
• 3095-95-2 diethylphosphonoacetic acid 

Downstream Products

• 760214-79-7 [(E)-(S)-1-benzyl-3-(2-isopropylamino-ethylcarbamoyl)-allyl]-carbamic acid tert-butyl ester 
• 267008-78-6 (E)-(S)-4-Amino-5-phenyl-pent-2-enoic acid 
• 760214-75-3 [(E)-(S)-1-benzyl-3-(2-dimethylamino-ethylcarbamoyl)-allyl]-carbamic acid tert-butyl ester 
• 760214-77-5 [(E)-(S)-1-benzyl-3-(2-diethylamino-ethylcarbamoyl)-allyl]-carbamic acid tert-butyl ester 
• 637001-67-3 (S,E)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpent-2-enoic acid 
• 195867-20-0 (4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpentanoic acid 
• 63328-06-3 (4R)-4-amino-5-phenylpentanoic acid 
• 269078-74-2 (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid 
• 756485-04-8 MDL 28170 
• 760214-57-1 (E)-(S)-4-[3-(4-phenoxy-phenyl)-ureido]-5-phenyl-pent-2-enoic acid 
• 760214-65-1 (E)-(S)-4-(3-biphenyl-4-yl-ureido)-5-phenyl-pent-2-enoic acid 

Relevant articles and documents

Design of Gallinamide A Analogs as Potent Inhibitors of the Cysteine Proteases Human Cathepsin L and Trypanosoma cruzi Cruzain

Gallinamide A, originally isolated with a modest antimalarial activity, was subsequently reisolated and characterized as a potent, selective, and irreversible inhibitor of the human cysteine protease cathepsin L. Molecular docking identified potential modifications to improve binding, which were synthesized as a suite of analogs. Resultingly, this current study produced the most potent gallinamide analog yet tested against cathepsin L (10, Ki = 0.0937 ± 0.01 nM and kinact/Ki = 8 730 000). From a protein structure and substrate preference perspective, cruzain, an essential Trypanosoma cruzi cysteine protease, is highly homologous. Our investigations revealed that gallinamide and its analogs potently inhibit cruzain and are exquisitely toxic toward T. cruzi in the intracellular amastigote stage. The most active compound, 5, had an IC50 = 5.1 ± 1.4 nM, but was relatively inactive to both the epimastigote (insect stage) and the host cell, and thus represents a new candidate for the treatment of Chagas disease.

HBTU mediated 1-hydroxybenzotriazole (HOBt) conjugate addition: Synthesis and stereochemical analysis of β-benzotriazole N-oxide substituted γ-amino acids and hybrid peptides

HBTU is a standard coupling agent commonly used for the activation of free carboxylic acids during the solution and solid phase peptide synthesis. 1-Hydroxybenzotriazole (HOBt) plays a significant role in reducing the racemization during peptide synthesis

GLYT2 MODULATORS

α-, β-, and γ-amino acid derivatives of formula I are disclosed as selective GlyT2 inhibitors for the treatment of central nervous system (CNS) conditions such as muscle spasticity, tinnitus, epilepsy and neuropathic pain. Formula I