5-Triethylsilylpent-4-yn-1-ol

Base Information

• Chemical Name: 5-Triethylsilylpent-4-yn-1-ol
• CAS No.: 174064-02-9
• Molecular Formula: C₁₁H₂₂OSi
• Molecular Weight: 198.381
• Hs Code.: 29310099
• DSSTox Substance ID: DTXSID40375300
• Wikidata: Q82163834
• Mol file: 174064-02-9.mol

Synonyms:174064-02-9;5-(Triethylsilyl)-4-pentyn-1-ol;5-triethylsilylpent-4-yn-1-ol;5-(triethylsilyl)pent-4-yn-1-ol;4-Pentyn-1-ol, 5-(triethylsilyl)-;5-triethylsilyl-4-pentyn-1-ol;4-Pentyn-1-ol,5-(triethylsilyl)-;DTXSID40375300;RDNBUIIPNLWRPB-UHFFFAOYSA-N;5-(triethylsilyl)-4-pentin-1-ol;AKOS006339863;AS-80527;CS-0448397;FT-0643664;S17622;A811604

Chemical Property of 5-Triethylsilylpent-4-yn-1-ol

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 0.00341mmHg at 25°C
• Refractive Index: 1.453
• Boiling Point: 250.6 °C at 760 mmHg
• Flash Point: 105.3 °C
• PSA: 20.23000
• Density: 0.875 g/cm³
• LogP: 2.81000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 198.143991855
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

98%min ^*data from raw suppliers

5-(Triethylsilyl)pent-4-yn-1-ol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: R36/37/38:
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

Useful:

• Canonical SMILES: CC[Si](CC)(CC)C#CCCCO

Technology Process of 5-Triethylsilylpent-4-yn-1-ol

There total 1 articles about 5-Triethylsilylpent-4-yn-1-ol 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: 95.0%

triethylsilyl chloride (994-30-9) + pent-1-yn-5-ol (5390-04-5) → 5-(triethylsilyl)pent-4-yn-1-ol (174064-02-9)

Guidance literature:

pent-1-yn-5-ol; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

triethylsilyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 5.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.10.069

Reference yield:

5-(triethylsilyl)pent-4-yn-1-ol (174064-02-9) → 11-(adamantan-1-ylmethoxy)-1,3,4,5-tetrakis-benzyloxy-undec-7-yne-2,6-dione (929619-32-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / Et₃N / CH₂Cl₂ / -40 - 20 °C

2.1: 97 percent / K₂CO₃ / CH₂Cl₂ / 72 h / Heating

3.1: 99 percent / NaOMe / tetrahydrofuran; methanol / 20 h / 90 °C

4.1: BuLi / tetrahydrofuran; toluene / 1 h / -50 °C

4.2: 77 percent / tetrahydrofuran; toluene / 2 h / -50 °C

5.1: NaBH₄ / methanol; CH₂Cl₂ / 2 h / 0 °C

6.1: (COCl)2; DMSO / CH₂Cl₂ / 4.42 h / -75 - -5 °C

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; sodium methylate; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; 6.1: Swern oxidation;

DOI:10.1021/jo061280p

Reference yield:

5-(triethylsilyl)pent-4-yn-1-ol (174064-02-9) → (1S)-2,3,4,6-tetra-O-benzyl-1-C-[5-(adamantan-1-yl-methoxy)-pent-1-ynyl]-1-deoxynojirimycin (850887-96-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 89 percent / Et₃N / CH₂Cl₂ / -40 - 20 °C

2.1: 97 percent / K₂CO₃ / CH₂Cl₂ / 72 h / Heating

3.1: 99 percent / NaOMe / tetrahydrofuran; methanol / 20 h / 90 °C

4.1: BuLi / tetrahydrofuran; toluene / 1 h / -50 °C

4.2: 77 percent / tetrahydrofuran; toluene / 2 h / -50 °C

5.1: NaBH₄ / methanol; CH₂Cl₂ / 2 h / 0 °C

6.1: (COCl)2; DMSO / CH₂Cl₂ / 4.42 h / -75 - -5 °C

7.1: NH₄HCO₂; 3 Angstroem molecular sieves / methanol; CH₂Cl₂ / 0 °C

7.2: 303 mg / NaBH₃CN / methanol; CH₂Cl₂ / 21 h / 0 - 20 °C

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 3 A molecular sieve; ammonium formate; sodium methylate; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; 6.1: Swern oxidation;

DOI:10.1021/jo061280p

upstream raw materials:

triethylsilyl chloride

pent-1-yn-5-ol

Downstream raw materials:

11-(adamantan-1-ylmethoxy)-1,3,4,5-tetrakis-benzyloxy-undec-7-yne-2,6-dione

(1S)-2,3,4,6-tetra-O-benzyl-1-C-[5-(adamantan-1-yl-methoxy)-pent-1-ynyl]-1-deoxynojirimycin

(1S)-2,3,4,6-tetra-O-benzyl-N-butyl-1-C-[5-(adamantan-1-yl-methoxy)-pent-1-ynyl]-1-deoxynojirimycin

C₁₇H₂₆BrNOSi

Refernces

• 1、 Wennekes, Tom,Van Den Berg, Richard J. B. H. N.,Donker, Wilma,Van Der Marel, Gijsbert A.,Strijland, Anneke,Aerts, Johannes M. F. G.,Overkleeft, Herman S.. "Development of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives as selective inhibitors of glucosylceramide metabolism in man". . p. 1088 - 1097. Retrieved 2007/10/03.