5390-04-5

Basic information

• Product Name: 4-Pentyn-1-ol
• Synonyms: 4-PENTYNE-1-OL;4-PENTYN-1-OL;1-Pentyn-5-ol;4-Pentyn-1-ol, 98+%;4-Pentin-1-ol 97%;1-Pentyne-5-ol;4-Pentynyl alcohol;4-Pentyn-1-ol,97%
• CAS NO: 5390-04-5
• Molecular Formula: C₅H₈O
• Molecular Weight: 84.12
• EINECS: 226-383-6
• Product Categories: Miscellaneous;Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Organic Building Blocks;Terminal
• Mol File: 5390-04-5.mol
• Article Data: 25

Chemical Properties

• Melting Point: -24.1°C (estimate)
• Boiling Point: 154-155 °C(lit.)
• Flash Point: 143 °F
• Appearance: Clear yellow/Liquid
• Density: 0.904 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.2mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• PKA: 14.81±0.10(Predicted)
• Water Solubility: Miscible with water.
• BRN: 1736712
• CAS DataBase Reference: 4-Pentyn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentyn-1-ol(5390-04-5)
• EPA Substance Registry System: 4-Pentyn-1-ol(5390-04-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: 1987
• WGK Germany: 3
• F: 10
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 5390-04-5(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow liquid

Uses

4-Pentyn-1-ol is an alkyne alcohol that is used as an initiator in ring-opening polymerization reactions. 4-Pentyn-1-ol is capable of undergoing cyclosisomerization, and is also used as a reactant in the synthesis of (+)-Serinolamide A, a cannabinoid CB1 receptor agonist.

General Description

Mechanism of (THF)W(CO)5-promoted endo- and exo-cycloisomerization of 4-pentyn-1-ol was studied.

InChI:InChI=1/C5H8O/c1-2-3-4-5-6/h1,6H,3-5H2

Synthetic route

Tetrahydrofurfuryl chloride (3003-84-7) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With n-butyllithium In hexane at 0℃; for 2h; Solvent; Temperature;	99.9%
With ammonia; sodium amide	91%
With Iron(III) nitrate nonahydrate; ammonia; sodium Cooling with acetone-dry ice;	89%

carbonic acid pent-4-ynyl ester 2,2,2-trichloro-ethyl ester → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With indium; water; ammonium chloride In methanol for 0.5h; Heating;	98%

(2R,3R)-3-Heptadecafluorooctyl-2-pent-4-ynyloxy-tetrahydro-pyran → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With methanol; toluene-4-sulfonic acid In tetrahydrofuran at 70℃; for 24h; deprotection of alcoholic OH;	94%

5-(2-propenyloxy)-1-pentyne (130018-34-7) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
quinoline-2-carboxylic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In methanol at 30℃; for 3h; Conversion of starting material;	94%
With quinoline-2-carboxylic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate In methanol at 30℃; for 3h;	94 % Chromat.

1-methoxy-4-pent-4-ynyloxymethyl-benzene (197219-01-5) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 21℃; for 0.25h;	91%

trichloroacetic acid pent-4-ynyl ester → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With indium; water; ammonium chloride In methanol for 0.5h; Heating;	87%

4-pentynoic acid (6089-09-4) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;	85%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;

1-(tetrahydropyranyloxy)-4-pentyn (62992-46-5) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With indium(III) triflate In methanol; water at 0 - 20℃; for 10h;	82%
With pyridinium p-toluenesulfonate In ethanol at 25℃; for 3h;

5-benzyloxy-1-pentyne (57618-47-0) → pent-1-yn-5-ol (5390-04-5) + benzoic acid (65-85-0)

Conditions	Yield
With bis(acetylacetonate)oxovanadium; methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate at 120℃; for 48h;	A 60% B 62%

nitrite de pentyne-4 ol-1 (30428-24-1) → 4-butanolide (96-48-0) + 4-pentyn-1-al (18498-59-4) + pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
In benzene at 10 - 20℃; for 18h; Irradiation;	A 2% B n/a C 38%
In benzene at 10 - 20℃; for 18h; Product distribution; Irradiation; examination of further acetylenic nitrites, reaction time;	A 2% B n/a C 38%

tetrahydrofuran (109-99-9) + 5-tert-Butylperoxy-pent-1-yne → 2-tert-butoxytetrahydrofuran (1927-59-9) + pent-1-yn-5-ol (5390-04-5) + 2-(pent-4-yn-1-yloxy)tetrahydrofuran (190184-80-6) + (E)-5-(Tetrahydro-furan-2-yl)-pent-4-en-1-ol + 2-((E)-5-tert-Butylperoxy-pent-1-enyl)-tetrahydro-furan + trans-2-[5-(2-tetrahydrofuryl)pent-4-enyloxy]tetrahydrofurane

Conditions	Yield
With tert-butyl peroxyacetate at 110℃; for 12h; Product distribution; Mechanism;	A 5% B 5% C 8% D n/a E n/a F n/a

3-chlorotetrahydropyran (6581-54-0) → 3,4-dihydro-2H-pyran (110-87-2) + pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With ammonia; sodium amide

3,4-dihydro-2H-pyran (110-87-2) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With n-pentylsodium; Petroleum ether
With n-butyllithium; Petroleum ether

2-methyleneoxolane (18137-88-7) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With n-pentylsodium; Petroleum ether
With n-butyllithium; Petroleum ether

5-chloro-3,4-dihydro-2H-pyran (6581-49-3) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With tetrahydrofuran; sodium

5-bromo-3,4-dihydro-2H-pyran (26274-19-1) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With butylsodium; Petroleum ether

4,5-dibromo-1-pentanol (59287-66-0) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With ammonia; sodium amide

1-methoxy-4-pentyne (14604-44-5) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
durch Entmethylieren;

ethyl 4-pentynoate (63093-41-4) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With tetrahydrofuran; potassium m-borate

4-chloro-5-methyl-2,3-dihydro-furan (50596-94-6) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
With lithium diisopropyl amide

nitrite de pentyne-4 ol-1 (30428-24-1) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
(photolysis);

Tetrahydrofurfuryl alcohol (97-99-4) → pent-1-yn-5-ol (5390-04-5)

Tetrahydrofurfuryl chloride (3003-84-7) + ammonia (7664-41-7) + sodium amide → pent-1-yn-5-ol (5390-04-5)

2-methyleneoxolane (18137-88-7) + n-pentylsodium (1822-71-5) + petroleum ether → pent-1-yn-5-ol (5390-04-5)

3-chlorotetrahydropyran (6581-54-0) + ammonia (7664-41-7) + sodium amide → 3,4-dihydro-2H-pyran (110-87-2) + pent-1-yn-5-ol (5390-04-5)

tetrahydrofuran (109-99-9) + 5-chloro-3,4-dihydro-2H-pyran (6581-49-3) + sodium → 3,4-dihydro-2H-pyran (110-87-2) + pent-1-yn-5-ol (5390-04-5)

3,4-dihydro-2H-pyran (110-87-2) + n-pentylsodium (1822-71-5) + petroleum ether → 3,4-dihydro-2H-pyran-6-carboxylic acid (31518-14-6) + pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
anschliessend mit festem Kohlendioxid;

TETRAHYDROPYRANE (142-68-7) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrachloromethane / 25 - 35 °C / Einleiten von Chlor in Gegenwart von Jod 2: lithium alanate; diethyl ether 3: sodium amide; liquid ammonia View Scheme

2,3-dichlorotetrahydro-2H-pyran (5631-95-8) → pent-1-yn-5-ol (5390-04-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: sodium amide; liquid ammonia View Scheme

3,4-dihydro-2H-pyran (110-87-2) + pent-1-yn-5-ol (5390-04-5) → 1-(tetrahydropyranyloxy)-4-pentyn (62992-46-5)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane for 4.5h; Ambient temperature;	100%
With hydrogenchloride In dichloromethane Ambient temperature;	100%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2.5h;	100%

pent-1-yn-5-ol (5390-04-5) → 5-Hydroxy-2-pentanone (1071-73-4)

Conditions	Yield
With C20H44Cl4N8O4P4Pd2S2; water at 30℃; for 9h; Reagent/catalyst;	100%
With cisplatin In water at 37℃; for 120h;	67%
With water; mercury(II) sulfate

pent-1-yn-5-ol (5390-04-5) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(tert-butyldimethylsilyloxy)-4-pentyne (61362-77-4)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 25℃;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 4h; Inert atmosphere;	100%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;	100%

chloro-trimethyl-silane (75-77-4) + pent-1-yn-5-ol (5390-04-5) → 5-trimethylsilanyl-pent-4-yn-1-ol (13224-84-5)

Conditions	Yield
With n-butyllithium Inert atmosphere;	100%
Stage #1: chloro-trimethyl-silane; pent-1-yn-5-ol With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water for 3h; Inert atmosphere;	100%
Stage #1: pent-1-yn-5-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.08333h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃;	100%

iodobenzene (591-50-4) + pent-1-yn-5-ol (5390-04-5) → 5-phenylpent-4-yn-1-ol (24595-58-2)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 12h;	100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 12h;	99%

pent-1-yn-5-ol (5390-04-5) + para-iodoanisole (696-62-8) → 5-(4'-methoxyphenyl)-4-pentyn-1-ol (154477-03-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20℃; for 4.5h; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 5h; Sonogashira Cross-Coupling; Inert atmosphere;	99%
With copper(l) iodide; palladium diacetate; triphenylphosphine In diethylamine at 20℃; Inert atmosphere;	89%

pent-1-yn-5-ol (5390-04-5) + methanesulfonyl chloride (124-63-0) → pent-4-yn-1-yl methanesulfonate (68275-03-6)

Conditions	Yield
With triethylamine In dichloromethane at -20℃; for 0.583333h;	100%
With triethylamine In dichloromethane at 0℃; for 1h;	100%
With triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;	100%

pent-1-yn-5-ol (5390-04-5) + tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyl-pent-4-ynyloxy-diphenyl-silane (91266-03-4)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide	100%
With 1H-imidazole In dichloromethane at 25℃;	100%
With 1H-imidazole In dichloromethane at 0℃; for 1h; Inert atmosphere;	100%

pent-1-yn-5-ol (5390-04-5) + 2,5-dibromobenzoic acid methyl ester (57381-43-8) → methyl 2,5-bis(5-hydroxy-1-pentynyl)benzoate (857349-10-1)

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 50℃; Sonogashira reaction;	100%

pent-1-yn-5-ol (5390-04-5) + para-diiodobenzene (624-38-4) → 1,4-bis(5-hydroxy-1-pentynyl)benzene (857348-95-9)

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 50℃; for 24h; Sonogashira reaction;	100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In dichloromethane at 50℃; Sonogashira Cross-Coupling;

pent-1-yn-5-ol (5390-04-5) → pentan-1-ol (71-41-0)

Conditions	Yield
Stage #1: pent-1-yn-5-ol With pyridinium p-toluenesulfonate In 1,2-dichloro-ethane at 80℃; for 20h; Stage #2: With triethylamine In dichloromethane at 20℃; for 6h; Stage #3: With trifluoroacetic acid In methanol; dichloromethane at 140℃; for 0.0666667h; microwave irradiation; Further stages.;	100%

TETRAHYDROPYRANE (142-68-7) + pent-1-yn-5-ol (5390-04-5) → 1-(tetrahydropyranyloxy)-4-pentyn (62992-46-5)

Conditions	Yield
With camphor-10-sulfonic acid In dichloromethane at 0 - 20℃; for 3h;	100%

pent-1-yn-5-ol (5390-04-5) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 1-((triisopropylsilyl)oxy)-4-pentyne (184370-68-1)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at -78℃;	100%

pent-1-yn-5-ol (5390-04-5) + N,N'-bis-Boc-S-methyl-isothiourea (322474-21-5) → N,N-bis(tert-butoxycarbonyl)-methyl pent-4-yn-1-ylcarbamimidothioate (1325688-35-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -10 - 50℃; for 0.75h; Microwave irradiation;	100%
With di-isopropyl azodicarboxylate; triphenylphosphine In water at -10 - 50℃; for 0.5h; Mitsunobu reaction; Microwave irradiation;	98%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -10 - 50℃; for 0.5h;	98%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -10 - 50℃; Microwave irradiation;

pent-1-yn-5-ol (5390-04-5) + benzyl azide (622-79-7) → 3-(1-benzyl-1H-1,2,3-triazol-4-yl)propan-1-ol (1198328-29-8)

Conditions	Yield
With copper(ll) sulfate pentahydrate; (+)-sodium L-ascorbate In water; tert-butyl alcohol at 20℃; for 2h;	100%
With CuO-600 In water; tert-butyl alcohol at 20℃; for 12h;	96%
With copper-iron nanoparticles In water at 20℃; for 12h; Huisgen cycloaddition; Inert atmosphere; regioselective reaction;	89%

pent-1-yn-5-ol (5390-04-5) + 1-(2-iodo-phenyl)-1H-pyrrole (157017-41-9) → 5-(2-(1H-pyrrol-1-yl)phenyl)pent-4-yn-1-ol (1404452-38-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 25℃; for 16h; Sonogashira Cross-Coupling; Inert atmosphere;	100%

pent-1-yn-5-ol (5390-04-5) + 7-amino-6-iodo-3-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-1H-1,8-naphthyridin-2-one → 7-amino-6-(5-hydroxypent-1-ynyl)-3-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-1H-1,8-naphthyridin-2-one

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20℃; for 0.333333h; Sonogashira Cross-Coupling;	100%

1-Boc-2-benzylpiperazine + pent-1-yn-5-ol (5390-04-5) + bis(trichloromethyl) carbonate (32315-10-9) → C22H30N2O4

Conditions	Yield
Stage #1: pent-1-yn-5-ol; bis(trichloromethyl) carbonate With pyridine In dichloromethane at 0℃; for 0.5h; Stage #2: 1-Boc-2-benzylpiperazine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;	100%

pent-1-yn-5-ol (5390-04-5) + 3-(4-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione → 3-(4-(5-hydroxypent-1-yn-1-yl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; Sealed tube; Inert atmosphere;	80%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 20h; Inert atmosphere; Sealed tube;	58%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; Sealed tube; Inert atmosphere;	2.08 g

methylsulphinyl chloride (676-85-7) + pent-1-yn-5-ol (5390-04-5) → 4-pentynyl methanesulfinate

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere;	100%

pent-1-yn-5-ol (5390-04-5) → 4-pentynoic acid (6089-09-4)

Conditions	Yield
With Jones reagent In acetone at 20℃; for 1h;	99%
With Jones reagent In acetone at 0 - 20℃; for 1h;	82%
With Jones reagent In acetone at 0 - 20℃; for 1h;	82%

pent-1-yn-5-ol (5390-04-5) + pivaloyl chloride (3282-30-2) → pent-4-yn-1-yl 2,2-dimethylpropanoate (140872-91-9)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	99%
With dmap; triethylamine In dichloromethane at 20℃; for 15h; Inert atmosphere; Schlenk technique;	99%
With pyridine In dichloromethane for 1h; 0 to 25 deg C;	95%
With pyridine; dmap In dichloromethane at 0 - 25℃; Inert atmosphere;	80%
With pyridine; dmap at 0 - 20℃; Inert atmosphere;	76%

pent-1-yn-5-ol (5390-04-5) + benzyl bromide (100-39-0) → 5-benzyloxy-1-pentyne (57618-47-0)

Conditions	Yield
Stage #1: pent-1-yn-5-ol With 1H-imidazole; sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	99%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 5h;	94%
Stage #1: pent-1-yn-5-ol With sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;	94%

pent-1-yn-5-ol (5390-04-5) + isobutene (115-11-7) → 5-tert-Butoxy-pent-1-yne (119649-74-0)

Conditions	Yield
With Amberlyst 15 hydrogen form In hexane at 20℃; for 4h;	99%
Amberlyst H-15 In hexane Ambient temperature; Yield given;

pent-1-yn-5-ol (5390-04-5) + o-iodo-methyl-benzoic acid (610-97-9) → 2-(5-hydroxypent-1-ynyl)benzoic acid methyl ester (152771-70-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 15h; Sonogashira Cross-Coupling; Inert atmosphere;	99%
With copper(l) iodide; triethylamine; trans-bis(triphenylphosphine)palladium(II) chloride at 25℃; for 12h;	92%
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) Sonogashira coupling reaction;	86%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 55℃; Sonogashira coupling;	85%
Stage #1: o-iodo-methyl-benzoic acid With triethylamine for 0.0833333h; Inert atmosphere; Stage #2: pent-1-yn-5-ol With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃; for 7h; Sonogashira coupling; Inert atmosphere;	84%

pent-1-yn-5-ol (5390-04-5) + o-nitroiodobenzene (609-73-4) → 2-(5-hydroxy-1-pentynyl)nitrobenzene (442155-83-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira coupling;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 14h; Sonogashira coupling;	92%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 25℃; for 16h; Sonogashira cross-coupling;	91%
Stage #1: pent-1-yn-5-ol; o-nitroiodobenzene With bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine In N,N-dimethyl-formamide for 0.5h; Sonogashira coupling; Inert atmosphere; Stage #2: With copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 5.16667h; Sonogashira coupling; Inert atmosphere;	83%

pent-1-yn-5-ol (5390-04-5) + 2-iodophenylamine (615-43-0) → 2-(5-hydroxy-1-pentyn-1-yl)aniline (380415-68-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine	99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine Inert atmosphere;	75%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 16h; Schlenk technique;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 10h; Inert atmosphere;

pent-1-yn-5-ol (5390-04-5) → (E)-3-penten-1-ol (764-37-4)

Conditions	Yield
With water; ruthenium hydroxyapatite at 80℃; for 24h; Product distribution; Further Variations:; Catalysts; anti-Markovnikov hydration;	99%

pent-1-yn-5-ol (5390-04-5) + dimethylglyoxal (431-03-8) → 3,8-dihydroxy-3-methyloct-4-yn-2-one

Conditions	Yield
johnphos In tetrahydrofuran at 40℃;	99%
With acetylacetonatodicarbonylrhodium(l); johnphos In tetrahydrofuran at 40℃; for 24h;	91%
With johnphos; acetylacetonatodicarbonylrhodium(l) In tetrahydrofuran at 40℃; for 24h;	91%

Upstream product

• 6581-54-0 3-chlorotetrahydropyran 
• 3003-84-7 Tetrahydrofurfuryl chloride 
• 110-87-2 3,4-dihydro-2H-pyran 
• 6581-49-3 5-chloro-3,4-dihydro-2H-pyran 
• 26274-19-1 5-bromo-3,4-dihydro-2H-pyran 
• 14604-44-5 1-methoxy-4-pentyne 
• 50596-94-6 4-chloro-5-methyl-2,3-dihydro-furan 
• 109-99-9 tetrahydrofuran 
• 130018-34-7 5-(2-propenyloxy)-1-pentyne 
• 57618-47-0 5-benzyloxy-1-pentyne 
• 53293-00-8 hex-5-ynoic acid 
• 18137-88-7 2-methyleneoxolane 
• 100911-02-2 acetic acid-(4,5-dibromo-pentyl ester) 
• 1576-85-8 4-pentenyl acetate 

Downstream Products

• 21890-96-0 7-(tetrahydro-2H-pyran-2-yloxy)hept-3-yn-1-ol 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 49826-98-4 Non-4-yn-1-ol 
• 32114-34-4 hex-2-yne-1,6-diol 
• 1487-15-6 2-Methyl-4,5-dihydrofuran 
• 28077-72-7 1-bromo-4-pentyne 
• 14267-92-6 1-chloro-4-pentyne 
• 1071-73-4 5-Hydroxy-2-pentanone 
• 6089-09-4 4-pentynoic acid 
• 70283-74-8 deca-4,6-diyne-1,10-diol 
• 61362-77-4 5-[tert-butyldimethylsilyloxy]pent-1-yne 
• 77875-85-5 4-pentyn-1-yl 4-methylbenzoate 
• 77758-50-0 4-pentynyl-1-tosylate 
• 111341-52-7 (E/Z)-5-phenylthio-4-penten-1-ol 

Relevant articles and documents

METHOD FOR PRODUCING 4-PENTYN-1-OL

PROBLEM TO BE SOLVED: To provide a production method that can synthesize 4-pentyn-1-ol, which is useful as a synthetic raw material of agrochemicals or pharmaceuticals, without using any special reaction facility, in high yields, and in large quantity. SOLUTION: A method for producing 4-pentyn-1-ol includes causing the reaction between 2-chloromethyltetrahydrofuran and butyllithium to occur in an ether solvent excluding tetrahydrofuran. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir

A practical and asymmetric synthesis of a functionalized trans-cyclopropoxy building block for the preparation of the HCV NS3/4a protease inhibitor grazoprevir is reported. Intramolecular SN2 displacement-ring closure, followed by a Baeyer-Villiger oxidation, yields the desired trans-cyclopropanol with full control of diastereoselectivity. A terminal alkyne is then effectively installed using LiNH(CH2)2NEt2. Starting from (S)-epichlorohydrin, the cyclopropoxy building block is prepared in 51% overall yield with >99.8% optical purity without isolation of any intermediates.

Enzyme kinetics and inhibition of histone acetyltransferase KAT8

Lysine acetyltransferase 8 (KAT8) is a histone acetyltransferase (HAT) responsible for acetylating lysine 16 on histone H4 (H4K16) and plays a role in cell cycle progression as well as acetylation of the tumor suppressor protein p53. Further studies on its biological function and drug discovery initiatives will benefit from the development of small molecule inhibitors for this enzyme. As a first step towards this aim we investigated the enzyme kinetics of this bi-substrate enzyme. The kinetic experiments indicate a ping-pong mechanism in which the enzyme binds Ac-CoA first, followed by binding of the histone substrate. This mechanism is supported by affinity measurements of both substrates using isothermal titration calorimetry (ITC). Using this information, the KAT8 inhibition of a focused compound collection around the non-selective HAT inhibitor anacardic acid has been investigated. Kinetic studies with anacardic acid were performed, based on which a model for the catalytic activity of KAT8 and the inhibitory action of anacardic acid (AA) was proposed. This enabled the calculation of the inhibition constant Ki of anacardic acid derivatives using an adaptation of the Cheng-Prusoff equation. The results described in this study give insight into the catalytic mechanism of KAT8 and present the first well-characterized small-molecule inhibitors for this HAT.