810670-02-1

Basic information

• Product Name: Methyl (R)-3-acetamido-3-(4-methoxyphenyl)propanoate
• Synonyms: (R)-methyl-3-acetamido-3-(4-methoxyphenyl)propanoate;METHYL (R)-3-ACETAMIDO-3-(4-METHOXYPHENYL)PROPANOATE
• CAS NO: 810670-02-1
• Molecular Formula: C13H17NO4
• Molecular Weight: 251.28
• Mol File: 810670-02-1.mol

Chemical Properties

• Boiling Point: 440.3oC at 760 mmHg
• Flash Point: 220.1oC
• Appearance: /
• Density: 1.129g/cm3
• Vapor Pressure: 5.97E-08mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: Methyl (R)-3-acetamido-3-(4-methoxyphenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (R)-3-acetamido-3-(4-methoxyphenyl)propanoate(810670-02-1)
• EPA Substance Registry System: Methyl (R)-3-acetamido-3-(4-methoxyphenyl)propanoate(810670-02-1)

Safety Data

• Hazardous Substances Data: 810670-02-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
Methyl (R)-3-acetamido-3-(4-methoxyphenyl)propanoate is utilized as a key building block in the synthesis of new medications. Its structure and properties contribute to the development of potential therapeutic agents, enhancing the discovery and creation of novel pharmaceuticals.
Used as a Reference Standard in Analytical Chemistry:
Due to its distinctive characteristics, Methyl (R)-3-acetamido-3-(4-methoxyphenyl)propanoate serves as a reference standard in analytical chemistry. It aids in the accurate measurement and analysis of various compounds, ensuring the reliability and precision of chemical assays and tests.
Used in Organic Synthesis and Medicinal Chemistry:
Methyl (R)-3-acetamido-3-(4-methoxyphenyl)propanoate's structure and properties make it an important building block in organic synthesis and medicinal chemistry. It plays a crucial role in the development of complex organic molecules and pharmaceutical agents, contributing to advancements in these scientific fields.

InChI:InChI=1/C13H17NO4/c1-9(15)14-12(8-13(16)18-3)10-4-6-11(17-2)7-5-10/h4-7,12H,8H2,1-3H3,(H,14,15)/t12-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 1333-74-0 hydrogen 
• 434957-24-1 (Z)-methyl 3-acetamido-3-(4-methoxyphenyl)-2-propenoate 
• 552838-52-5 methyl 3-acetamido-3-(4-methoxyphenyl)-2-propenoate 
• 654061-84-4 methyl 3-amino-3-(4-methoxyphenyl)acrylate 
• 22027-50-5 methyl 3-(4-methoxybenzoyl)acetate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Relevant articles and documents

Nickel-catalyzed enantioselective umpolung hydrogenation for stereoselective synthesis of β-amido esters

Nickel complexes ligated by strongly donating diphosphines catalyze enantioselective hydrogenation for the preparation of acyclic and cyclic β-amido esters. A combination of acetic acid and indium powder provides protons and electrons to form nickel hydrido complexes under umpolung hydrogenation conditions.

Nickel-catalyzed enantioselective hydrogenation of β-(acylamino)acrylates: Synthesis of chiral β-amino acid derivatives

The nickel-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates has been developed, affording chiral β-amino acid derivatives with excellent yields (95-99% yield) and enantioselectivities (97-99% ee). With the Ni-Binapine system, high enantioselectivities (98-99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of β-alkyl and β-aryl β-(acylamino)acrylates. The synthesis of chiral β-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.

Nickel-catalyzed asymmetric transfer hydrogenation of olefins for the synthesis of α- And β-amino acids

The field of asymmetric (transfer) hydrogenation of prochiral olefins has been dominated by noble metal catalysts based on rhodium, ruthenium, and iridium. Herein we report that a simple nickel catalyst is highly active in the transfer hydrogenation using

Electron-donating and rigid p-stereogenic bisphospholane ligands for highly enantioselective rhodium-catalyzed asymmetric hydrogenations

More electron donating, more rigid: A new highly electron-donating P-stereogenic bisphospholane ligand (ZhangPhos) was synthesized in a practical and highly enantioselective manner from a commercially available chiral source. Better or comparable enantioselectivities and reactivities than TangPhos were achieved in rhodium-catalyzed hydrogenation of various functionalized olefins (see scheme; nbd=3,5-norbornadiene). Copyright

Readily available chiral phosphine-aminophosphine ligands derived from 1-phenylethylamine for Rh-catalyzed enantioselective hydrogenations

A series of new chiral phosphine-aminophosphine ligands have been prepared via a two- or three-step transformation from commercially available and inexpensive (S)-1-phenylethylamine, and successfully used in the rhodium-catalyzed asymmetric hydrogenation

Chiral 1-phenylethylamine-derived phosphine-phosphoramidite ligands for highly enantioselective Rh-catalyzed hydrogenation of β-(acylamino) acrylates: Significant effect of substituents on 3,3′-positions of binaphthyl moiety

A series of new chiral phosphine-phosphoramidite ligands with a 3,3′-substituted binaphthyl moiety were prepared from 1-phenylethylamine, and successfully applied in the Rh-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates. The research disclosed that the substituents on the 3,3′-positions of binaphthyl moiety significantly influenced the enantioselectivity.

Highly efficient iridium-catalyzed asymmetric hydrogenation of unprotected β-enamine esters

A highly efficient and enantioselective hydrogenation of unprotected β-enamine esters catalyzed by Ir-(S,S)-f-Binaphane complex has been developed. This methodology provides straightforward access to free β-amino acids in high yields with excellent enantioselectivities up to 97% ee and high reactivities (TON > 5000).

Modular phosphine-aminophosphine ligands based on chiral 1,2,3,4-tetrahydro-1-naphthylamine backbone: A new class of practical ligands for enantioselective hydrogenations

A series of new chiral phosphine-aminophosphine ligands [(R)-HW-Phos] has been prepared from (R)-1,2,3,4-tetrahydro-1-naphthylamine through a two-step procedure, and successfully applied in the rhodium-catalyzed asymmetric hydrogenation of various functionalized olefins such as α-enol ester phosphonates, α-enamido phosphonates, (Z)-β-(acylamino)acrylates and so on. Excellent enantioselectivities have been achieved in the hydrogenation of most substrates tested, demonstrating the high potential of these newly developed phosphine-aminophosphine ligands in asymmetric catalysis. The present research also discloses that these newly developed phosphine-aminophosphine ligands are more efficient than that derived from (S)-1-phenylethylamine, suggesting that the increased rigidity conferred by a cyclohexyl fragment in these phosphine-aminophosphine ligands has a positive effect in the asymmetric induction.

Practical Rh(I)-catalyzed asymmetric hydrogenation of β-(acylamino) acrylates using a new unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligand: Crucial influence of an N-H proton in the ligand

(Chemical Equation Presented) Excellent enantioselectivities and high turnovers (S/C = 5000) were achieved in the Rh(I)-catalyzed asymmetric hydrogenation of both β-aryl-and β-alkyl-β-(acylamino)acrylates with a new unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligand, and the presence of an N-H proton in the ligand was demonstrated to have a crucial role in the enantioselectivity.

Practical P-chiral phosphane ligand for Rh-catalyzed asymmetric hydrogenation

A highly electron-donating and conformationally rigid P-chiral bis(trialkylphospholane) ligand 2 (DuanPhos) has been prepared in both enantiomeric forms through a concise synthesis. Rh-2 complex has exhibited remarkably high enantio-selectivities (up to >99% ee) and reactivities (up to 10,000 TON) for the hydrogenation of a wide variety of functionalized prochiral alkenes (5 different types), which provides a very practical catalytic system for the preparation of various synthetically useful chiral compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.