Thiarubrine C, (E)-

Base Information

• Chemical Name: Thiarubrine C, (E)-
• CAS No.: 65710-89-6
• Molecular Formula: C13H10S2
• Molecular Weight: 230.3485
• UNII: 36D59DE461
• DSSTox Substance ID: DTXSID80191041
• Nikkaji Number: J720.476K
• Wikidata: Q27256554
• Metabolomics Workbench ID: 77266
• ChEMBL ID: CHEMBL2285706
• Mol file: 65710-89-6.mol

Synonyms:Thiarubrine C, (E)-;trans-Thiarubrin C;THIARUBRINE C;Thiarubrin C, trans-;Thiarubrin C, (E)-;Thiarubrine C [MI];UNII-36D59DE461;36D59DE461;UNII-U6YM108M6L;3760-30-3;O-Dithiin, 3-(3,5-hexadien-1-ynyl)-6-(1-propynyl)-, (E)-;1,2-Dithiin, 3-(3,5-hexadien-1-ynyl)-6-(1-propynyl)-, (E)-;65710-89-6;O-dithiin, 3-(3,5-hexadien-1-ynyl)-5-(1-propynyl)-;1,2-Dithiin, 3-(3,5-hexadien-1-ynyl)-6-(1-propynyl)-;1,2-Dithiin, 3-(3,5-hexadien-1-yn-1-yl)-6-(1-propyn-1-yl)-;(E)-3-(hexa-3,5-dien-1-yn-1-yl)-6-(prop-1-yn-1-yl)-1,2-dithiine;(E)-thiarubrine c;U6YM108M6L;CHEMBL2285706;DTXSID80191041;LMFA12000370;Q27256554

Chemical Property of Thiarubrine C, (E)-

Chemical Property:

• Vapor Pressure: 0.00114mmHg at 25°C
• Boiling Point: 309.8°Cat760mmHg
• Flash Point: 154.5°C
• Density: 1.18g/cm³
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 230.02239267
• Heavy Atom Count: 15
• Complexity: 464

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CC1=CC=C(SS1)C#CC=CC=C
• Isomeric SMILES: CC#CC1=CC=C(SS1)C#C/C=C/C=C

Technology Process of Thiarubrine C, (E)-

There total 4 articles about Thiarubrine C, (E)- 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:

(3Z,5Z)-1,1,8,8-Tetrabromo-3,6-bis-(2-trimethylsilanyl-ethylsulfanyl)-octa-1,3,5,7-tetraene (218444-53-2) → thiarubrine C (65710-89-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi, 2.) MeI / 1.) THF, -78 deg C to room temperature, 1 h, 2.) THF, -78 deg C to room temperature, 12 h

2: Pd(PPh₃)4, CuI, BuNH₂ / benzene / 1 h / Ambient temperature

3: Pd(PPh₃)4 / tetrahydrofuran; benzene / 12 h / Ambient temperature

4: 1.) TBAF, (F₃CCO)2O, 2.) I₂, KI / 1.) THF, -40 deg C to room temperature, 4 h, 2.) H₂O, room temperature, 15 min

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrabutyl ammonium fluoride; iodine; N-butylamine; trifluoroacetic anhydride; potassium iodide; methyl iodide; In tetrahydrofuran; benzene;

DOI:10.1021/jo981849p

Reference yield:

(3Z,5Z)-3,6-Bis-(2-trimethylsilanyl-ethylsulfanyl)-nona-3,5-diene-1,7-diyne (218444-54-3) → thiarubrine C (65710-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Pd(PPh₃)4, CuI, BuNH₂ / benzene / 1 h / Ambient temperature

2: Pd(PPh₃)4 / tetrahydrofuran; benzene / 12 h / Ambient temperature

3: 1.) TBAF, (F₃CCO)2O, 2.) I₂, KI / 1.) THF, -40 deg C to room temperature, 4 h, 2.) H₂O, room temperature, 15 min

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; iodine; N-butylamine; trifluoroacetic anhydride; potassium iodide; In tetrahydrofuran; benzene;

DOI:10.1021/jo981849p

Reference yield:

(1Z,5Z,7Z)-1-Chloro-5,8-bis-(2-trimethylsilanyl-ethylsulfanyl)-undeca-1,5,7-triene-3,9-diyne (1026247-56-2) → thiarubrine C (65710-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Pd(PPh₃)4 / tetrahydrofuran; benzene / 12 h / Ambient temperature

2: 1.) TBAF, (F₃CCO)2O, 2.) I₂, KI / 1.) THF, -40 deg C to room temperature, 4 h, 2.) H₂O, room temperature, 15 min

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; iodine; trifluoroacetic anhydride; potassium iodide; In tetrahydrofuran; benzene;

DOI:10.1021/jo981849p

upstream raw materials:

(3Z,7Z,9Z)-7,10-Bis-(2-trimethylsilanyl-ethylsulfanyl)-trideca-1,3,7,9-tetraene-5,11-diyne

(3Z,5Z)-1,1,8,8-Tetrabromo-3,6-bis-(2-trimethylsilanyl-ethylsulfanyl)-octa-1,3,5,7-tetraene

(3Z,5Z)-3,6-Bis-(2-trimethylsilanyl-ethylsulfanyl)-nona-3,5-diene-1,7-diyne

(1Z,5Z,7Z)-1-Chloro-5,8-bis-(2-trimethylsilanyl-ethylsulfanyl)-undeca-1,5,7-triene-3,9-diyne

Refernces