4H-Thiopyran-4-one, tetrahydro-3-[(1R)-2-nitro-1-phenylethyl]-, (3S)-

Base Information

• Chemical Name: 4H-Thiopyran-4-one, tetrahydro-3-[(1R)-2-nitro-1-phenylethyl]-, (3S)-
• CAS No.: 360062-52-8
• Molecular Formula: C13H15NO3S
• Molecular Weight: 265.333
• Mol file: 360062-52-8.mol

Synonyms:

Chemical Property of 4H-Thiopyran-4-one, tetrahydro-3-[(1R)-2-nitro-1-phenylethyl]-, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4H-Thiopyran-4-one, tetrahydro-3-[(1R)-2-nitro-1-phenylethyl]-, (3S)-

There total 4 articles about 4H-Thiopyran-4-one, tetrahydro-3-[(1R)-2-nitro-1-phenylethyl]-, (3S)- 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%

Tetrahydrothiopyran-4-one (1072-72-6) + nitrostyrene (5153-67-3) → (S)-3-[(S)-2-nitro-1-phenyl-ethyl]-tetrahydro-thiopyran-4-one (360062-52-8) + (R)-3-[(R)-2-nitro-1-phenyl-ethyl]-tetrahydro-thiopyran-4-one + anti-3-(2-nitro-1-phenylethyl)-tetrahydro-thiopyran-4-one

Guidance literature:

Tetrahydrothiopyran-4-one; With 3,5-dinitrobenzoic acid; 1-butyl-3-methylimidazolium (3R,5S)-5-(methoxycarbonyl)-pyrrolidin-3-yl sulfate; at 4 ℃; for 0.5h; Ionic liquid;

nitrostyrene; at 4 ℃; for 48h; Ionic liquid;

DOI:10.1002/ejoc.201201068

Reference yield:

Tetrahydrothiopyran-4-one (1072-72-6) + nitrostyrene (5153-67-3) → (R)-3-((S)-2-nitro-1-phenylethyl)-tetrahydro-thiopyran-4-one + (S)-3-[(S)-2-nitro-1-phenyl-ethyl]-tetrahydro-thiopyran-4-one (360062-52-8) + (R)-3-[(R)-2-nitro-1-phenyl-ethyl]-tetrahydro-thiopyran-4-one + (S)-3-((R)-2-nitro-1-phenylethyl)dihydro-2H-thiopyran-4(3H)-one

Guidance literature:

With trifluoroacetic acid; sodium chloride; (S)-N-decyl-N-(pyrrolidin-2-ylmethyl)decan-1-amine; at 25 ℃; for 96h; Title compound not separated from byproducts;

DOI:10.1021/ja060338e

Reference yield:

Tetrahydrothiopyran-4-one (1072-72-6) + nitrostyrene (5153-67-3) → (R)-3-((S)-2-nitro-1-phenylethyl)-tetrahydro-thiopyran-4-one + (S)-3-[(S)-2-nitro-1-phenyl-ethyl]-tetrahydro-thiopyran-4-one (360062-52-8) + (R)-3-[(R)-2-nitro-1-phenyl-ethyl]-tetrahydro-thiopyran-4-one

Guidance literature:

With (R)-2-((S)-2-Amino-propionylamino)-propionic acid; In 1-methyl-pyrrolidin-2-one; water; dimethyl sulfoxide; at 4 ℃; for 48h; Title compound not separated from byproducts;

DOI:10.1002/adsc.200505373

upstream raw materials:

Tetrahydrothiopyran-4-one

nitrostyrene

Refernces

• 1、 Lu, Hanbin,Lv, Jiamin,Zhou, Canhua,Zhou, Mi,Fang, Yanxiong,Dong, Jinxiang,Kato, Terumasa,Liu, Yan,Maruoka, Keiji. "Remarkable Effect of tert-Amine Additives in the Asymmetric Direct Michael Reaction of Ketones with β-Arylnitroethenes Catalyzed by an L-Hydroxyproline-Based Amino Tf-Amide Organocatalyst". supporting information. p. 1909 - 1912. Retrieved 2021/04/05.
• 2、 McCooey, Seamus H.,Connon, Stephen J.. "Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins". . p. 599 - 602. Retrieved 2008/02/02.