190189-97-0

Basic information

• Product Name: Methyl (3S)-3-Boc-amino-3-phenylpropionate
• Synonyms: Methyl (3S)-3-Boc-amino-3-phenylpropionate;Methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate;(S)-METHYL 3-((TERT-BUTOXYCARBONYL)AMINO)-3-PHENYLPROPANOATE
• CAS NO: 190189-97-0
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33154
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates
• Mol File: 190189-97-0.mol
• Article Data: 23

Chemical Properties

• Melting Point: 95-96℃
• Boiling Point: 398.7°C at 760 mmHg
• Flash Point: 195°C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 1.44E-06mmHg at 25°C
• Refractive Index: 1.504
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: Methyl (3S)-3-Boc-amino-3-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (3S)-3-Boc-amino-3-phenylpropionate(190189-97-0)
• EPA Substance Registry System: Methyl (3S)-3-Boc-amino-3-phenylpropionate(190189-97-0)

Safety Data

• Hazardous Substances Data: 190189-97-0(Hazardous Substances Data)

Usage

Description

Methyl (3S)-3-Boc-amino-3-phenylpropionate, with the CAS number 190189-97-0, is a white solid compound that is primarily utilized in the field of organic synthesis. It is a derivative of amino acids, featuring a unique structure that includes a Boc-protected amino group and a phenyl group attached to a propionate backbone. Methyl (3S)-3-Boc-amino-3-phenylpropionate is known for its stability and reactivity, making it a valuable building block in the synthesis of various organic molecules.

Uses

Used in Organic Synthesis:
Methyl (3S)-3-Boc-amino-3-phenylpropionate is used as a synthetic building block for the creation of complex organic molecules. Its unique structure allows for a wide range of applications in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. The Boc-protected amino group provides a versatile handle for further functionalization, while the phenyl group can be used to introduce aromaticity and improve the compound's solubility in organic solvents.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl (3S)-3-Boc-amino-3-phenylpropionate is used as an intermediate in the synthesis of various drug candidates. Its ability to be easily modified and incorporated into larger molecular frameworks makes it a valuable tool for medicinal chemists working on the development of new therapeutic agents. The compound's stability and reactivity also contribute to its utility in the synthesis of complex drug molecules.
Used in Agrochemical Industry:
Methyl (3S)-3-Boc-amino-3-phenylpropionate is also employed in the agrochemical industry for the synthesis of novel compounds with potential applications as pesticides, herbicides, or plant growth regulators. The compound's structural diversity and synthetic versatility make it an attractive starting material for the development of new agrochemical products.

InChI:InChI=1/C15H21NO4/c1-15(2,3)20-14(18)16-12(10-13(17)19-4)11-8-6-5-7-9-11/h5-9,12H,10H2,1-4H3,(H,16,18)/t12-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 37088-66-7 (3S)-methyl 3-amino-3-phenylpropanoate 
• 909804-54-2 2-(tert-butoxycarbonylamino-phenyl-methyl)-malonic acid dimethyl ester 
• 103365-47-5 (S)-3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 890043-61-5 (S)-2-(tert-butoxycarbonylaminophenylmethyl)malonic acid dibenzyl ester 
• 103-26-4 methyl cinnamate 
• 24608-52-4 tert-butyl chloroformate 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 956101-46-5 tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate 
• 125414-45-1 (2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol 
• 257861-35-1 (E)-(4S)-4-(N-benzyl)amino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexylethyl]oxy-4-phenyl-1-butene 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 959123-35-4 tert-butyl (1R,2R)-2-methoxycarbonyl-2-hydroxy-1-phenylethylcarbamate 

Downstream Products

• 135865-78-0 tert-butyl (1S)-3-oxo-1-phenylpropylcarbamate 
• 718611-17-7 S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 1425667-56-6 (S,E)-tert-butyl [3-oxo-1-phenyl-hex-4-enyl]carbamate 
• 1425666-97-2 (S)-tert-butyl [4-(diethoxyphosphoryl)-3-oxo-1-phenylbutyl]carbamate 
• 1425667-67-9 C₁₉H₂₇NO₄ 
• 1425667-65-7 C₁₉H₂₇NO₄ 

Relevant articles and documents

New amino acid clubbed Schiff bases inhibit carbonic anhydrase II, α-glucosidase, and urease enzymes: in silico and in vitro

Combating pathological conditions related to hyperactivity of enzymes remains a formidable challenge for health. Small molecules therapy constitutes one of the means to circumvent the medical disorders resulting from enzyme hyperactivity. In this regard, we have synthesized structurally diverse amino acid hybrid Schiff bases (5a–5l and 10a–10k) and evaluated them for carbonic anhydrase II, α-glucosidase, and urease inhibitory potential. These new chemical scaffolds showed variable efficacies against the selected enzymes. The results indicated that compounds 5b (11.8 ± 1.33 μM), 10i (83.3 ± 1.13 μM), and 10f (88.2 ± 2.27 μM) are the most active scaffolds against carbonic anhydrase II, α-glucosidase, and urease, respectively. A structure–activity relationship revealed the most structural features contributing to the overall activities. Molecular docking suggested that these compounds possess excellent binding interactions with the active site residues of the targets by interacting through hydrogen bonding, π–π, and π–cation interactions.

Asymmetric Mannich Reaction and Construction of Axially Chiral Sulfone-Containing Styrenes in One Pot from α-Amido Sulfones Based on the Waste-Reuse Strategy

A simultaneous asymmetric Mannich reaction and the construction of axially chiral sulfone-containing styrenes in one pot from α-amido sulfones based on the waste-reuse strategy was demonstrated. A series of chiral β-amino diesters and axially chiral sulfone-containing styrenes with various functional groups were synthesized in good to excellent yields and enantioselectivities under mild conditions. In addition, this protocol has been successfully applied to synthesize the anti-HIV drug Maraviroc and chiral trichloro derivatives.

Disulfonimide-catalyzed asymmetric synthesis of β3-amino esters directly from N-Boc-amino sulfones

An asymmetric Mannich reaction of silyl ketene acetals with N-Boc-amino sulfones has been developed. A chiral disulfonimide efficiently catalyzes both the in situ generation of the corresponding N-Boc imines and the asymmetric Mannich reaction with excellent yields and enantioselectivities. Kinetic studies confirm a proposed stepwise mechanism.