(S)-4-methoxy-3-(naphthalen-2-ylmethyl)-4-oxobutanoic acid

Base Information

• Chemical Name: (S)-4-methoxy-3-(naphthalen-2-ylmethyl)-4-oxobutanoic acid
• CAS No.: 220497-75-6
• Molecular Formula: C₁₆H₁₆O₄
• Molecular Weight: 272.301
• Hs Code.: 29171990
• Nikkaji Number: J1.859.514A
• Mol file: 220497-75-6.mol

Synonyms:220497-75-6;(S)-4-methoxy-3-(naphthalen-2-ylmethyl)-4-oxobutanoic acid;(S)-2-(2-NAPHTHYLMETHYL)SUCCINIC ACID-1-METHYL ESTER;(S)-4-Methoxy-3-(2-naphthylmethyl)-4-oxobutanoic Acid;A4742;AKOS015901756;AC-26765;(S)-2-(2-Naphthylmethyl)butanedioic acid 1-methyl ester;(S)-4-methoxy-3-(naphthalen-2-ylmethyl)-4-oxobutanoicacid;(3S)-4-methoxy-3-[(naphthalen-2-yl)methyl]-4-oxobutanoic acid

Chemical Property of (S)-4-methoxy-3-(naphthalen-2-ylmethyl)-4-oxobutanoic acid

Chemical Property:

• Vapor Pressure: 3.31E-09mmHg at 25°C
• Melting Point: 65 oC
• Refractive Index: 1.5447 (estimate)
• Boiling Point: 458.7oC at 760mmHg
• Flash Point: 170.6oC
• PSA: 63.60000
• Density: 1.1858 (rough estimate)
• LogP: 2.64620
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 272.10485899
• Heavy Atom Count: 20
• Complexity: 352

Purity/Quality:

99.3% ^*data from raw suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC2=CC=CC=C2C=C1)CC(=O)O
• Isomeric SMILES: COC(=O)[C@@H](CC1=CC2=CC=CC=C2C=C1)CC(=O)O

Technology Process of (S)-4-methoxy-3-(naphthalen-2-ylmethyl)-4-oxobutanoic acid

There total 4 articles about (S)-4-methoxy-3-(naphthalen-2-ylmethyl)-4-oxobutanoic 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:

4-(2-naphthyl)-3-(methoxycarbonyl)-3-butenoic acid (493008-38-1) → (R)-2-(2-naphthylmethyl)succinic acid 1-methyl ester (220497-75-6)

Guidance literature:

With hydrogen; sodium methylate; (Z,Z)-cycloocta-1,5-diene(S,S-1,2-bis(2,5-diethylphospholanyl)benzene)rhodium(I) tetrafluoroborate; In methanol; for 12h; under 4125.3 Torr; Ambient temperature;

DOI:10.1002/(SICI)1521-3773(19980803)37:13/14<1931::AID-ANIE1931>3.0.CO;2-3

Reference yield:

(E)-2-(2-naphthylmethylene)succinic acid 1-methyl ester (17917-19-0) → (R)-2-(2-naphthylmethyl)succinic acid 1-methyl ester (220497-75-6)

Guidance literature:

With [Rh((R,R)-iPr-JDayPhos)(MeOH)₂]BF₄; hydrogen; In methanol; at 22 ℃; for 0.25h; under 2250.23 Torr; enantioselective reaction; Autoclave;

DOI:10.1002/adsc.201800255

Reference yield:

Dimethyl succinate (106-65-0) → (R)-2-(2-naphthylmethyl)succinic acid 1-methyl ester (220497-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; sodium / 7 h / Inert atmosphere; Reflux

2: [Rh((R,R)-iPr-JDayPhos)(MeOH)₂]BF₄; hydrogen / methanol / 0.25 h / 22 °C / 2250.23 Torr / Autoclave

With methanol; [Rh((R,R)-iPr-JDayPhos)(MeOH)₂]BF₄; hydrogen; sodium; In methanol; 1: |Stobbe Condensation;

DOI:10.1002/adsc.201800255

upstream raw materials:

4-(2-naphthyl)-3-(methoxycarbonyl)-3-butenoic acid

(E)-2-(2-naphthylmethylene)succinic acid 1-methyl ester

Dimethyl succinate

β-naphthaldehyde

Refernces

• 1、 Burk, Mark J.,Bienewald, Frank,Harris, Michael,Zanotti-Gerosa, Antonio. "Practical access to 2-alkylsuccinates through asymmetric catalytic hydrogenation of Stobbe-derived itaconates". . p. 1931 - 1933. Retrieved 2007/10/03.