(S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone

Base Information

• Chemical Name: (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone
• CAS No.: 101979-45-7
• Molecular Formula: C8H13NOS2
• Molecular Weight: 203.329
• Hs Code.: 2934999090
• Mol file: 101979-45-7.mol

Synonyms:(4S)-N-acetyl-4-(prop-2-yl)-1,3-thiazolidine-2-thione;;QC-8202;;(S)-N-acetyl-4-isopropyl-1,3-thiozolidine-2-thione;;(S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione;;(S)-N-acetyl-4-isopropyl-1,3-thiazolidine-2-thione;;(S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone;;

Chemical Property of (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone

Chemical Property:

• Melting Point: 67-68 oC (dichloromethane )**
• Boiling Point: 279.6±23.0 oC (760 Torr), Calc.*
• Flash Point: 122.9±22.6 oC, Calc.*
• PSA: 77.70000
• Density: 1.22±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• LogP: 1.82910

Purity/Quality:

99% ^*data from raw suppliers

Ethanone,1-[(4S)-4-(1-methylethyl)-2-thioxo-3-thiazolidinyl]- 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone

There total 5 articles about (S)-1-(4-isopropyl-2-thioxothiazolidin-3-yl)ethanone 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: 100.0%

(S)-4-isopropylthiazolidine-2-thione (76186-04-4) + acetyl chloride (75-36-5) → (S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione (101979-45-7)

Guidance literature:

With pyridine; In dichloromethane; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1039/d1ob00883h

Reference yield: 67.0%

carbon disulfide (75-15-0,12122-00-8) + (S)-valinol (2026-48-4,473-75-6) + acetyl chloride (75-36-5) → (S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione (101979-45-7)

Guidance literature:

carbon disulfide; (S)-valinol; With potassium hydroxide; for 40h; Heating; Inert atmosphere; Schlenk technique;

acetyl chloride; With sodium hydride; at 0 ℃; Inert atmosphere; Schlenk technique;

DOI:10.3390/molecules24183228

Reference yield: 35.0%

acetic pivalic mixed anhydride (7137-32-8) + (S)-4-isopropylthiazolidine-2-thione (76186-04-4) → (S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione (101979-45-7)

Guidance literature:

(S)-4-isopropylthiazolidine-2-thione; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

acetic pivalic mixed anhydride; In tetrahydrofuran; at -78 ℃; for 5h;

DOI:10.1002/anie.200352652

upstream raw materials:

(S)-4-isopropylthiazolidine-2-thione

acetyl chloride

acetic pivalic mixed anhydride

(S)-valinol

Downstream raw materials:

(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

C₂₀H₂₇NO₃S₂

C₂₉H₄₁NO₃S₂Si

Refernces

• 1、 Nagao,Dai,Ochiai,Shiro. "New general asymmetric synthesis of versatile γ-alkylated butenolides and its application to expeditious synthesis of the chiral Geissman-Waiss lactones useful for (+)-retronecine synthesis". . p. 5211 - 5217. Retrieved 1989.
• 2、 McNulty, James,McLeod, David,Jenkins, Hilary A.. "Enantioselective Total Synthesis of the Proposed Structure of the Endophytic Fungal Metabolite Phomolide G: Structural Revision and Unambiguous Stereochemical Assignment". . p. 688 - 692. Retrieved 2016.
• 3、 Nesman, Jannicke Irina,Primdahl, Karoline Gangestad,Tungen, J?rn Eivind,Palmas, Fransesco,Dalli, Jesmond,Hansen, Trond Vidar. "Synthesis, structural confirmation, and biosynthesis of 22-OH-PD1n-3 DPA?". . . Retrieved 2019.
• 4、 Nesman, Jannicke Irina,Tungen, J?rn Eivind,Vik, Anders,Hansen, Trond Vidar. "Stereoselective synthesis of the specialized pro-resolving and anti-inflammatory mediator resolvin E1". . . Retrieved 2020.