3-heptyn-1-ol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With sodium hydride; Trimethylenediamine at 20℃; for 0.666667h; Isomerization; | 100% |
With potassium tert-butylate; sodium hydride; Trimethylenediamine In mineral oil at 20 - 70℃; for 3h; | 99% |
With potassium tert-butylate; lithium; Trimethylenediamine at 20℃; for 2h; | 97% |
hept-6-ynoic acid
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 100% |
Stage #1: hept-6-ynoic acid With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; Stage #2: With hydrogenchloride In diethyl ether for 0.5h; | 89% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | 82% |
hep-2-yn-1-ol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With potassium hydride; 1,2-diaminopropan In tetrahydrofuran; mineral oil at 20℃; for 24h; Inert atmosphere; | 99% |
With potassium salt of 1,3-diaminopropane In tetrahydrofuran at 0℃; for 0.5h; | 97% |
With potassium tert-butylate; lithium; Trimethylenediamine at 20℃; for 3h; Inert atmosphere; | 90% |
tetrahydro-2-(6-heptynyloxy)-2H-pyran
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With acid | 98% |
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol | 95% |
methyl hept-6-ynoate
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Heating; | 91% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 2h; Yield given; | |
With methanol; sodium tetrahydroborate In tetrahydrofuran for 3.25h; Reflux; | 2.15 g |
7-(trimethylsilyl)hept-6-yn-1-yl acetate
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With water; potassium carbonate In methanol at 20℃; for 5h; | 82% |
hept-5-yn-1-ol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With sodium amide; Trimethylenediamine In ammonia | 79% |
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Dehydrobromination; | 70% |
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With lithium triethylborohydride In tetrahydrofuran at -78 - 20℃; | 63% |
7-chlorohept-1-yne
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Ueberfuehrung ueber das Jodid in das Acetat und folgende Hydrolyse; | |
(i) DMF, KOAc, (ii) NaOH, aq. EtOH; Multistep reaction; |
6-bromohept-6-en-1-ol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With ammonia; sodium amide |
Conditions | Yield |
---|---|
With 3,4-dihydro-2H-pyran Multistep reaction; |
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 20℃; |
2-nonyn-1-ol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With potassium tert-butylate; lithium; Trimethylenediamine |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C 2: 79 percent / KH; 1,3-diaminopropane / 2 h / cooling View Scheme | |
Multi-step reaction with 2 steps 1: 87 percent / n-BuLi / tetrahydrofuran; hexane / Heating 2: 70 percent / KH; H2N(CH2)2NH2 / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 1.2: 99 percent / tetrahydrofuran / 18 h / -78 - 20 °C 2.1: 67 percent / potassium hydride / various solvent(s) / 1.5 h / 10 - 15 °C View Scheme |
non-2-ynyl tetrahydropyran-2-yl ether
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: PPTS / ethanol / 3 h / 25 °C 2: H2N(CH2)3NH2; Li; t-BuOK View Scheme |
1,6-hexanediol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: NaH / tetrahydrofuran / 20 °C 2: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 °C 3: PPh3 / CH2Cl2 / 20 °C 4: n-BuLi / tetrahydrofuran / 0 °C 5: aq. HCl / methanol / 20 °C View Scheme |
6-((triisopropylsilyl)oxy)hexanal
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: PPh3 / CH2Cl2 / 20 °C 2: n-BuLi / tetrahydrofuran / 0 °C 3: aq. HCl / methanol / 20 °C View Scheme |
6-{[tris(propan-2-yl)silyl]oxy}hexan-1-ol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 °C 2: PPh3 / CH2Cl2 / 20 °C 3: n-BuLi / tetrahydrofuran / 0 °C 4: aq. HCl / methanol / 20 °C View Scheme |
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / 0 °C 2: aq. HCl / methanol / 20 °C View Scheme |
5-bromopentanoic acid
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dimethylsulfoxide / 2 h 2: SOCl2 / 3 h / Heating 3: 91 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: NH3 / tetrahydrofuran / 15 h 2: diethyl ether 3: LiAlH4 / diethyl ether / 2 h / 0 °C View Scheme |
TETRAHYDROPYRANE
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ZnBr2 2: K2CO3 / methanol 3: 1.) dihydropyran, 2.) deprotection View Scheme |
5-bromo-1-pentanyl acetate
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: K2CO3 / methanol 2: 1.) dihydropyran, 2.) deprotection View Scheme |
2-(chloromethyl)tetrahydropyran
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 83 percent / NaNH2 / liquid ammonia 2: 54 percent / LiNH2 / liquid ammonia 3: 79 percent / NaNH2, H2N-(CH2)3-NH2 / liquid ammonia View Scheme |
Tetrahydropyran-2-methanol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: SOCl2, pyridine 2: 83 percent / NaNH2 / liquid ammonia 3: 54 percent / LiNH2 / liquid ammonia 4: 79 percent / NaNH2, H2N-(CH2)3-NH2 / liquid ammonia View Scheme |
5-hexyl-1-ol
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 54 percent / LiNH2 / liquid ammonia 2: 79 percent / NaNH2, H2N-(CH2)3-NH2 / liquid ammonia View Scheme |
hex-1-yne
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / n-BuLi / tetrahydrofuran 2: 46 percent / KH, 1,3-Diaminopropane View Scheme | |
Multi-step reaction with 2 steps 1: n-butyllithium / diethyl ether / 0 °C 2: sodium hydride; ethylenediamine / 60 °C View Scheme |
3,4-dihydro-2H-pyran
1-hydroxy-6-heptyne
tetrahydro-2-(6-heptynyloxy)-2H-pyran
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 20℃; | 100% |
With toluene-4-sulfonic acid | 98% |
camphor-10-sulfonic acid In dichloromethane at 0 - 20℃; | 97% |
1-hydroxy-6-heptyne
tert-butyldimethylsilyl chloride
tert-butyl(hept-6-yn-1-yloxy)dimethylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 24h; | 100% |
With 1H-imidazole In dichloromethane at 20℃; for 24h; | 100% |
With pyridine; 1H-imidazole at 20℃; for 0.5h; | 99% |
1-hydroxy-6-heptyne
2-bromo-4'-methoxy-benzophenone
Conditions | Yield |
---|---|
Stage #1: 2-bromo-4'-methoxy-benzophenone With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 20℃; for 0.5h; Sealed tube; Inert atmosphere; Stage #2: 1-hydroxy-6-heptyne at 85℃; for 48h; Sealed tube; Inert atmosphere; | 99% |
1-hydroxy-6-heptyne
o-iodo-methyl-benzoic acid
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 15h; Sonogashira Cross-Coupling; Inert atmosphere; | 99% |
1-hydroxy-6-heptyne
hept-5-yn-1-ol
Conditions | Yield |
---|---|
With potassium hydroxide | 98% |
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 3h; | 88% |
1-hydroxy-6-heptyne
hept-6-ynal
Conditions | Yield |
---|---|
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -60 - 0℃; Swern oxidation; | 98% |
With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction; | 89% |
With sulfur trioxide pyridine complex; triethylamine In dichloromethane; dimethyl sulfoxide at 20℃; for 1h; Schlenk technique; | 87% |
1-hydroxy-6-heptyne
tert-butylchlorodiphenylsilane
tert-butyl(hept-6-yn-1-yloxy)diphenylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 25℃; | 98% |
With 1H-imidazole In dichloromethane at 0 - 20℃; | 94% |
With 1H-imidazole In dichloromethane at 0 - 20℃; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
Stage #1: 1-hydroxy-6-heptyne With dmap; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane for 2h; Inert atmosphere; | 97% |
Stage #1: 1-hydroxy-6-heptyne With dmap; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane for 2h; Inert atmosphere; | 92% |
Stage #1: 1-hydroxy-6-heptyne With dmap; n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; | 80% |
Stage #1: 1-hydroxy-6-heptyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; for 15h; Inert atmosphere; | 70% |
Stage #1: 1-hydroxy-6-heptyne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.333333h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; | 61% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine for 7h; Sonogashira Cross-Coupling; Inert atmosphere; | 97% |
1-hydroxy-6-heptyne
7-iodo-6-heptyn-1-ol
Conditions | Yield |
---|---|
With potassium hydroxide; iodine In methanol; water at 20℃; for 4h; | 94% |
With potassium hydroxide; iodine In methanol at 20℃; for 4h; | 94% |
Stage #1: 1-hydroxy-6-heptyne With potassium hydroxide In methanol; water at 0℃; for 0.166667h; Stage #2: With iodine In methanol; water at 0 - 20℃; | 77% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 3h; Sonogashira Cross-Coupling; Inert atmosphere; | 93% |
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With silver(I) azide; trimethylsilylazide; water In dimethyl sulfoxide at 80℃; Reagent/catalyst; | 93% |
1-hydroxy-6-heptyne
benzyl bromide
((hept-6-yn-1-yloxy)methyl)benzene
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium hydride In tetrahydrofuran; diethyl ether for 3h; cooling; | 92% |
With sodium hydride In tetrahydrofuran at 0℃; | 78% |
1-hydroxy-6-heptyne
p-methoxybenzyl chloride
1-((hept-6-yn-1-yloxy)methyl)-4-methoxybenzene
Conditions | Yield |
---|---|
Stage #1: 1-hydroxy-6-heptyne With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; | 92% |
Stage #1: 1-hydroxy-6-heptyne With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 18h; Inert atmosphere; | 87% |
4-cyanopyridine N-oxide
1-hydroxy-6-heptyne
Conditions | Yield |
---|---|
With potassium fluoride; water; trifluoroacetic acid; nickel dichloride; zinc In N,N-dimethyl acetamide at 30℃; for 24h; | 92% |
1-hydroxy-6-heptyne
p-toluenesulfonyl chloride
hept-6-yn-1-yl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere; | 91% |
With pyridine | 87% |
With dmap; triethylamine Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 1h; | 91% |
1-hydroxy-6-heptyne
4-Iodobenzotrifluoride
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) at 20℃; Sonogashira reaction; | 91% |
1-hydroxy-6-heptyne
7-bromo-hept-1-yne
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1h; Cooling with ice; | 91% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 1.5h; Inert atmosphere; | 86% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere; | 83% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; | 54% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; Appel Halogenation; |
Conditions | Yield |
---|---|
With pyridine | 90% |
With dmap; triethylamine In dichloromethane at 20℃; for 5h; | 86% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; | 3.44 g |
1-hydroxy-6-heptyne
1-iodo-octa-1,3-diyne
pentadeca-6,8,10-triyn-1-ol
Conditions | Yield |
---|---|
With pyrrolidine; copper(l) iodide | 90% |
Conditions | Yield |
---|---|
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 20℃; Sonogashira Cross-Coupling; Inert atmosphere; | 90% |
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) at 20℃; Sonogashira reaction; | 87% |
With bis-triphenylphosphine-palladium(II) chloride; diethylamine; copper(l) chloride at 0 - 20℃; Sonogashira coupling; Inert atmosphere; | 39% |
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In toluene at 20℃; for 2h; |
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 90% |
4-bromo-2-methylbut-3-yn-2-ol
1-hydroxy-6-heptyne
10-methylundeca-6,8-diyne-1,10-diol
Conditions | Yield |
---|---|
Stage #1: 1-hydroxy-6-heptyne With propylamine; hydroxylamine hydrochloride; copper(l) chloride In water at 0℃; for 0.166667h; Cadiot-Chodkiewicz procedure; Stage #2: 4-bromo-2-methylbut-3-yn-2-ol In tetrahydrofuran at 0℃; Cadiot-Chodkiewicz procedure; | 90% |
The 6-Heptyn-1-ol with CAS registry number of 63478-76-2 is also known as 7-Hydroxyhept-1-yne. The IUPAC name is Hept-6-yn-1-ol. In addition, the formula is C7H12O and the molecular weight is 112.17. As this chemical is flammable, keep away from sources of ignition when using it.
Physical properties about 6-Heptyn-1-ol are: (1)ACD/LogP: 1.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.12; (4)ACD/LogD (pH 7.4): 1.12; (5)ACD/BCF (pH 5.5): 4.16; (6)ACD/BCF (pH 7.4): 4.16; (7)ACD/KOC (pH 5.5): 96.59; (8)ACD/KOC (pH 7.4): 96.59; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.452; (13)Molar Refractivity: 33.84 cm3; (14)Molar Volume: 125.3 cm3; (15)Surface Tension: 35.6 dyne/cm; (16)Density: 0.894 g/cm3; (17)Flash Point: 92.8 °C; (18)Enthalpy of Vaporization: 47.81 kJ/mol; (19)Boiling Point: 174.3 °C at 760 mmHg; (20)Vapour Pressure: 0.378 mmHg at 25 °C.
Preparation of 6-Heptyn-1-ol: it is prepared by reaction of 2-hept-6-ynyloxy-tetrahydro-pyran. The reaction needs reagent acid and the yield is about 98%.
Uses of 6-Heptyn-1-ol: it is used to produce Preparation of 6-Heptyn-1-ol by reaction with 3,4-dihydro-2H-pyran. The reaction occurs with reagent PPTS and solvent CH2Cl2 at the temperature of 20 °C for 12 hours. The yield is about 95%.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C#CCCCCCO
2. InChI: InChI=1S/C7H12O/c1-2-3-4-5-6-7-8/h1,8H,3-7H2
3. InChIKey: BVRCLEXKQNWTDK-UHFFFAOYSA-N
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