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4415-82-1

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4415-82-1 Usage

Chemical Properties

Colorless to Almost colorless clear liquid.

Uses

Cyclobutanemethanol was used in the synthesis of bicyclic lactone.

Application

Cyclobutanemethanol is a drug used to treat inflammatory diseases. It is an uptake inhibitor that blocks the transport of uridine into cells, preventing the activation of G-protein coupled receptors and the subsequent production of inflammatory mediators. Cyclobutanemethanol has been shown to have anti-inflammatory properties by inhibiting the CB2 receptor, which is found in large quantities in inflammatory tissues. It also prevents dehydration and increases blood flow to inflamed areas by acting on vascular endothelial cells. It has been shown to inhibit influenza virus replication in vitro, but not in vivo.

General Description

Oxidation of cyclobutanemethanol in the presence of lead tetraacetate and lead tetraacetate/metal chloride has been investigated.

Synthesis

Cyclobutanemethanol can be synthesized from two molecules of hydrochloric acid and one molecule of cyclobutane. The synthesis pathway includes removal of a hydroxy group and addition of an alkynyl group via hydrogen bonding interactions with chloride ions.

Check Digit Verification of cas no

The CAS Registry Mumber 4415-82-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,4,1 and 5 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 4415-82:
(6*4)+(5*4)+(4*1)+(3*5)+(2*8)+(1*2)=81
81 % 10 = 1
So 4415-82-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O/c6-4-5-2-1-3-5/h5-6H,1-4H2

4415-82-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclobutanemethanol

1.2 Other means of identification

Product number -
Other names Cyclobutylmethanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4415-82-1 SDS

4415-82-1Synthetic route

C8H18OSi

C8H18OSi

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;98%
Cyclobutanecarboxylic acid
3721-95-7

Cyclobutanecarboxylic acid

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 1.5h; Ambient temperature;96%
With lithium aluminium tetrahydride In diethyl ether72%
With lithium aluminium tetrahydride; diethyl ether
ethyl cyclobutylcarboxylate
14924-53-9

ethyl cyclobutylcarboxylate

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether 1) rt, 24 h, 2) reflux, 1.5 h;53%
With ethanol; sodium
Stage #1: ethyl cyclobutylcarboxylate With diethoxymethylane; zinc diacetate In toluene at 100℃; for 24h; Inert atmosphere;
Stage #2: With methanol; potassium hydroxide chemoselective reaction;
65 %Chromat.
ethanol
64-17-5

ethanol

diethyl cyclobutane-1,1-dicarboxylate
3779-29-1

diethyl cyclobutane-1,1-dicarboxylate

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With sodium; toluene
diethyl cyclobutane-1,1-dicarboxylate
3779-29-1

diethyl cyclobutane-1,1-dicarboxylate

A

[1-(hydroxymethyl)cyclobutyl]methanol
4415-73-0

[1-(hydroxymethyl)cyclobutyl]methanol

B

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With ethanol; sodium
With ethanol; sodium Erwaermen des Reaktionsgemisches auf 130-140grad;
(1-cyclobutenyl)methyl alcohol
89182-08-1

(1-cyclobutenyl)methyl alcohol

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With methanol; platinum Hydrogenation;
Cyclobutanecarbonyl chloride
5006-22-4

Cyclobutanecarbonyl chloride

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With diethyl ether; sodium
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating; Yield given;
methylidenecyclobutane
1120-56-5

methylidenecyclobutane

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
(i) B2H6, THF, (ii) H2O2; Multistep reaction;
cyclobutylaldehyde
2987-17-9

cyclobutylaldehyde

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With sodium hydroxide at 80℃; for 42h;
3-(hydroxymethyl)cyclobutene
15963-49-2

3-(hydroxymethyl)cyclobutene

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In methanol
5-bromo-1,2-epoxypentane
21746-87-2

5-bromo-1,2-epoxypentane

A

Cyclopentanol
96-41-3

Cyclopentanol

B

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With tributylphosphine; copper In tetrahydrofuran Product distribution; other reagent and solvent;
With tributylphosphine; copper In tetrahydrofuran Yield given. Yields of byproduct given;
With copper(l) iodide; lithium dihydronaphthylide radical; triphenylphosphine In tetrahydrofuran 1) -45 deg C, 5 min, -23 deg C, 3 h, r.t.; Yield given. Yields of byproduct given;
methylidenecyclobutane
1120-56-5

methylidenecyclobutane

A

1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

B

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

trans-2-methylcyclobutanol

trans-2-methylcyclobutanol

Conditions
ConditionsYield
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1.) THF, a) RT, 1.5 h, b) 110 deg C, 96 h, 2.) THF, water, 50 deg C to 60 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1.) THF, a) RT, 1.5 h, b) 110 deg C, 96 h, 2.) THF, water, 50 deg C to 60 deg C 1 h; Yield given. Multistep reaction. Yields of byproduct given;
cyclobutyl brosylate
51108-24-8

cyclobutyl brosylate

A

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

B

p-bromobenzene sulfonic acid
138-36-3

p-bromobenzene sulfonic acid

Conditions
ConditionsYield
With sodium methylate In ethanol; water at 45℃; Rate constant;
With sodium acetate In formic acid; acetic acid at 45℃; Rate constant;
2-(3-Iodo-propyl)-oxirane
99700-68-2

2-(3-Iodo-propyl)-oxirane

A

Cyclopentanol
96-41-3

Cyclopentanol

B

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With tert.-butyl lithium 1.) Et2O, pentane, -78 deg C, 5 min; 2.) warming; Yield given. Multistep reaction. Yields of byproduct given;
With tert.-butyl lithium In diethyl ether; pentane at -78℃; Product distribution; Effect of various additives or warming.;
diethyl ether
60-29-7

diethyl ether

Cyclobutanecarbonyl chloride
5006-22-4

Cyclobutanecarbonyl chloride

sodium

sodium

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

hydrochloride of aminomethyl-cyclobutane

hydrochloride of aminomethyl-cyclobutane

A

Cyclopentanol
96-41-3

Cyclopentanol

B

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
With silver(I) nitrite
ethanol
64-17-5

ethanol

diethyl cyclobutane-1,1-dicarboxylate
3779-29-1

diethyl cyclobutane-1,1-dicarboxylate

sodium

sodium

A

[1-(hydroxymethyl)cyclobutyl]methanol
4415-73-0

[1-(hydroxymethyl)cyclobutyl]methanol

B

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

sulfuric acid
7664-93-9

sulfuric acid

cyclobutylmethyl-cyclobutylmethylen-amine

cyclobutylmethyl-cyclobutylmethylen-amine

A

cyclobutylmethyl cyclobutanecarboxylate
38834-90-1

cyclobutylmethyl cyclobutanecarboxylate

B

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

cyclobutylmethylamine hydrochloride
5454-82-0

cyclobutylmethylamine hydrochloride

AgNO2

AgNO2

A

methylidenecyclobutane
1120-56-5

methylidenecyclobutane

B

Cyclopentanol
96-41-3

Cyclopentanol

C

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

D

cyclopentene
142-29-0

cyclopentene

Conditions
ConditionsYield
man erhitzt die Loesung des erhaltenen Nitrils;
methyl cyclobut-1-enecarboxylate
40628-41-9

methyl cyclobut-1-enecarboxylate

A

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

B

(1-cyclobutenyl)methyl alcohol
89182-08-1

(1-cyclobutenyl)methyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 25℃; for 0.25h; Reduction; Title compound not separated from byproducts.;
1-cyclobutenecarboxylic acid
23519-90-6

1-cyclobutenecarboxylic acid

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / diethyl ether / 0.5 h / 0 °C
2: lithium aluminum hydride / diethyl ether / 0.25 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / diethyl ether / 48 h / 20 °C
2: lithium aluminum hydride / diethyl ether / 0.25 h / 25 °C
View Scheme
diethyl cyclobutane-1,1-dicarboxylate
3779-29-1

diethyl cyclobutane-1,1-dicarboxylate

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) KOH / 1.) EtOH, H2O; 2.) reflux
2: thionyl chloride
3: lithium aluminum hydride / diethyl ether / 2 h / Heating
View Scheme
1-chloro-1-(hydroxymethyl)cyclobutane
81469-29-6

1-chloro-1-(hydroxymethyl)cyclobutane

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol. KOH-solution
2: platinum; methanol / Hydrogenation
View Scheme
3-chlorocyclobutane-1-carboxylic acid
35207-71-7

3-chlorocyclobutane-1-carboxylic acid

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) Et2O, (ii) LiAlH4
2: KOtBu / dimethylsulfoxide
3: H2 / PtO2 / methanol
View Scheme
cyclobutane-1,1-dicarboxylic acid dichloride
51816-01-4

cyclobutane-1,1-dicarboxylic acid dichloride

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: SO2Cl2, (PhCO)2O2 / 3 h / Heating
2: H2O
3: 12 h / 180 °C
4: (i) Et2O, (ii) LiAlH4
5: KOtBu / dimethylsulfoxide
6: H2 / PtO2 / methanol
View Scheme
cyclobutane-1,1'-dicarboxylic acid
5445-51-2

cyclobutane-1,1'-dicarboxylic acid

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: SOCl2 / 3 h / Heating
2: SO2Cl2, (PhCO)2O2 / 3 h / Heating
3: H2O
4: 12 h / 180 °C
5: (i) Et2O, (ii) LiAlH4
6: KOtBu / dimethylsulfoxide
7: H2 / PtO2 / methanol
View Scheme
3-chloro-1,1-cyclobutanedicarboxylic acid
89639-43-0

3-chloro-1,1-cyclobutanedicarboxylic acid

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 12 h / 180 °C
2: (i) Et2O, (ii) LiAlH4
3: KOtBu / dimethylsulfoxide
4: H2 / PtO2 / methanol
View Scheme
3-Chlor-1,1-cyclobutandicarbonsaeure-dichlorid
89582-02-5

3-Chlor-1,1-cyclobutandicarbonsaeure-dichlorid

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: H2O
2: 12 h / 180 °C
3: (i) Et2O, (ii) LiAlH4
4: KOtBu / dimethylsulfoxide
5: H2 / PtO2 / methanol
View Scheme
3-chlorocyclobutanemethanol
15963-47-0

3-chlorocyclobutanemethanol

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOtBu / dimethylsulfoxide
2: H2 / PtO2 / methanol
View Scheme
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

cyclobutylmethyl methanesulfonate
63659-30-3

cyclobutylmethyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 2h;100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3h;66%
With triethylamine In dichloromethane at -10℃; for 0.333333h;
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

cyclobutylaldehyde
2987-17-9

cyclobutylaldehyde

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 1h; Ambient temperature;99%
Stage #1: cyclobutanemethanol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at -5℃; for 0.333333h;
Stage #2: With sodium hypochlorite In dichloromethane; water at -5 - 0℃; for 0.5h;
Stage #3: With potassium dihydrogenphosphate In dichloromethane; water at 20℃; for 0.5h;
70.4%
Stage #1: cyclobutanemethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 1h;
Stage #2: With triethylamine In dichloromethane at -78℃;
63%
diethylphosphonoacetic acid
3095-95-2

diethylphosphonoacetic acid

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

cyclobutylmethyl 2-(diethoxyphosphoryl)acetate

cyclobutylmethyl 2-(diethoxyphosphoryl)acetate

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; ethyl acetate; toluene at 20℃; for 4h; Inert atmosphere;99%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

trichloroacetonitrile
545-06-2

trichloroacetonitrile

cyclobutylmethyl 2,2,2-trichloroacetimidate

cyclobutylmethyl 2,2,2-trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane99%
4-chlorophenyl acetate
876-27-7

4-chlorophenyl acetate

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

4-acetamidobenzenesulfonyl azide
2158-14-7

4-acetamidobenzenesulfonyl azide

cyclobutylmethyl 2-(4-chlorophenyl)-2-diazoacetate

cyclobutylmethyl 2-(4-chlorophenyl)-2-diazoacetate

Conditions
ConditionsYield
Stage #1: 4-chlorophenyl acetate; cyclobutanemethanol With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 20h;
Stage #2: 4-acetamidobenzenesulfonyl azide With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃; for 16h;
99%
phenylglyoxylyl chloride
25726-04-9

phenylglyoxylyl chloride

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

cyclobutylmethyl 2-oxo-2-phenylacetate

cyclobutylmethyl 2-oxo-2-phenylacetate

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 20℃; Inert atmosphere;98%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

anthranilic acid amide
28144-70-9

anthranilic acid amide

2-cyclobutylquinazolin-4(3H)-one

2-cyclobutylquinazolin-4(3H)-one

Conditions
ConditionsYield
With tert.-butylhydroperoxide In dimethyl sulfoxide at 25 - 35℃; for 40h; Irradiation; Green chemistry;98%
With tert.-butylhydroperoxide at 110℃; for 12h;74%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

cyclobutylmethyl 4-methylbenzenesulfonate
13295-53-9

cyclobutylmethyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With dmap In dichloromethane at 0 - 25℃;97%
In pyridine at 0℃; for 24h;92%
In pyridine at -15℃;92%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

1-cyano-2-methoxynaphthalene
16000-39-8

1-cyano-2-methoxynaphthalene

2-(cyclobutylmethoxy)-1-naphthonitrile

2-(cyclobutylmethoxy)-1-naphthonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 20℃; for 16h; Inert atmosphere; Sealed tube; Glovebox;96%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

puberulic acid
99-23-0

puberulic acid

C13H14O6

C13H14O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 120℃; for 16h; Sealed tube;95%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

C8H18OSi

C8H18OSi

Conditions
ConditionsYield
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.05h; Green chemistry;94%
2-cyanopyrimidine
14080-23-0

2-cyanopyrimidine

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

2-(cyclobutylmethoxy)pyrimidine

2-(cyclobutylmethoxy)pyrimidine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 5h;94%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

C25H26ClN3O2

C25H26ClN3O2

C30H35N3O3

C30H35N3O3

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 20 - 50℃; for 2.5h;91%
ditungsten hexa-tert-butoxide
57125-20-9

ditungsten hexa-tert-butoxide

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

W4(OCH2-c-Bu)12(HOCH2-c-Bu)
120853-44-3

W4(OCH2-c-Bu)12(HOCH2-c-Bu)

Conditions
ConditionsYield
In hexane byproducts: t-C4H9OH; under N2, adding cyclobutylmethanol dropwise to soln. of W2(O-t-Bu)6, room temp., stirring, 2 h; evapn. of volatile components in vac., dissolving in 1,2-dimethoxyethane, cooling to -20°C, 16 h, filtration at 0°C (2nd crop from filtrate); elem. anal.;90.2%
3-chloropyrazin-2-amine
6863-73-6

3-chloropyrazin-2-amine

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

3-(cyclobutylmethoxy)pyrazin-2-amine

3-(cyclobutylmethoxy)pyrazin-2-amine

Conditions
ConditionsYield
Stage #1: cyclobutanemethanol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 3-chloropyrazin-2-amine In N,N-dimethyl-formamide at 100℃; for 20h;
89%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

cyclobutylmethyl acetoacetate
103785-41-7

cyclobutylmethyl acetoacetate

Conditions
ConditionsYield
With sodium hydride at 70 - 80℃; for 2h;88%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoate
474295-85-7

methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanoate

methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-[4-(cyclobutylmethoxy)phenyl]propanoate

methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-[4-(cyclobutylmethoxy)phenyl]propanoate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 35℃; Mitsunobu Displacement; Inert atmosphere;87%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

N-(3-((1S,5S,6S)-3-amino-1-(methoxymethyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4,5-difluorophenyl)-5-chloro-2-pyrazinecarboxamide

N-(3-((1S,5S,6S)-3-amino-1-(methoxymethyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4,5-difluorophenyl)-5-chloro-2-pyrazinecarboxamide

N-(3-((1S,5S,6S)-3-amino-1-(methoxymethyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4,5-difluorophenyl)-5-(cyclobutylmethoxy)pyrazine-2-carboxamide

N-(3-((1S,5S,6S)-3-amino-1-(methoxymethyl)-5-methyl-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4,5-difluorophenyl)-5-(cyclobutylmethoxy)pyrazine-2-carboxamide

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran at 50℃; for 2h;86%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

cyclobutylmethyl sulfamate

cyclobutylmethyl sulfamate

Conditions
ConditionsYield
With formic acid; isocyanate de chlorosulfonyle; triethylamine In dichloromethane at 0 - 25℃; Schlenk technique; Inert atmosphere;86%
tert-butyl N-(4-bromo-1,3-thiazol-2-yl)carbamate
944804-88-0

tert-butyl N-(4-bromo-1,3-thiazol-2-yl)carbamate

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

tert-butyl (4-bromothiazol-2-yl)(cyclobutylmethyl)carbamate

tert-butyl (4-bromothiazol-2-yl)(cyclobutylmethyl)carbamate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 40℃; for 1.5h; Inert atmosphere;85%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

sodium formate
141-53-7

sodium formate

cyclohexene
110-83-8

cyclohexene

cyclobutylmethyl cyclohexanecarboxylate

cyclobutylmethyl cyclohexanecarboxylate

Conditions
ConditionsYield
With 2-Hydroxymethylpyridine; dodecacarbonyl-triangulo-triruthenium at 170℃; for 4h;84%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

Phenyl triflate
17763-67-6

Phenyl triflate

1-cyclobutyl-1-phenyl-methanone
5407-98-7

1-cyclobutyl-1-phenyl-methanone

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)nickel (0); acetone; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 130℃; for 20h; Inert atmosphere;84%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

sodium monochloroacetic acid

sodium monochloroacetic acid

cyclobutylmethoxyacetic acid
848666-52-4

cyclobutylmethoxyacetic acid

Conditions
ConditionsYield
Stage #1: cyclobutanemethanol With sodium hydride In tetrahydrofuran at -15 - 25℃; for 1h;
Stage #2: sodium monochloroacetic acid In dimethyl sulfoxide at 20℃; for 20h;
Stage #3: With hydrogenchloride In water
83%
Stage #1: cyclobutanemethanol With sodium hydride In tetrahydrofuran at -15 - 25℃; for 1h; pH=2;
Stage #2: sodium monochloroacetic acid In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 2h;
83%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

methyl cyclohexanethionocarboxylate
91923-30-7

methyl cyclohexanethionocarboxylate

O-(cyclobutylmethyl) cyclohexanecarbothioate

O-(cyclobutylmethyl) cyclohexanecarbothioate

Conditions
ConditionsYield
With sodium hydride at 75 - 80℃; for 0.5h;83%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

C14H11FO2

C14H11FO2

C19H20O3

C19H20O3

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere;81.5%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

potassium cyclobutanecarboxylate

potassium cyclobutanecarboxylate

Conditions
ConditionsYield
With C22H36IrNP(1+)*CF3O3S(1-); potassium hydroxide In toluene at 120℃; for 40h;81%
ethyl diazomethanesulfonate

ethyl diazomethanesulfonate

cyclobutanemethanol
4415-82-1

cyclobutanemethanol

((6-(3,3-bis(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl)hex-5-yn-1-yl)oxy)(tertbutyl)diphenylsilane

((6-(3,3-bis(trifluoromethyl)-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl)hex-5-yn-1-yl)oxy)(tertbutyl)diphenylsilane

ethyl 7-((tert-butyldiphenylsilyl)oxy)-1-(cyclobutylmethoxy)hept-2-yne-1-sulfonate

ethyl 7-((tert-butyldiphenylsilyl)oxy)-1-(cyclobutylmethoxy)hept-2-yne-1-sulfonate

Conditions
ConditionsYield
With tetrakis(actonitrile)copper(I) hexafluorophosphate In dichloromethane at 25℃; for 2h; Inert atmosphere; Sealed tube; Microwave irradiation;81%
cyclobutanemethanol
4415-82-1

cyclobutanemethanol

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

N′,N′-bis(cyclobutylmethyl)benzohydrazide

N′,N′-bis(cyclobutylmethyl)benzohydrazide

Conditions
ConditionsYield
With t-butylnitrite; C24H20N2O4Ru; sodium t-butanolate In tert-butyl alcohol at 130℃; for 24h; Schlenk technique; Inert atmosphere;81%

4415-82-1Relevant articles and documents

Perkin

, p. 329 (1901)

Cobalt Pincer Complexes for Catalytic Reduction of Carboxylic Acid Esters

Junge, Kathrin,Wendt, Bianca,Cingolani, Andrea,Spannenberg, Anke,Wei, Zhihong,Jiao, Haijun,Beller, Matthias

supporting information, p. 1046 - 1052 (2018/01/01)

A selection of cobalt(I) and cobalt(II) pincer type complexes with different substitution patterns was tested in the catalytic reduction of carboxylic acid esters to alcohols. The cobalt pincer type complex 4 is suitable for the hydrogenation of aromatic as well as aliphatic and cyclic esters. Mechanistic investigation indicated a metal ligand cooperated reaction pathway.

Synthesis method of analgesic intermediate bromomethyl cyclobutane

-

Paragraph 0009; 0010; 0011; 0012; 0013; 0014, (2017/07/21)

The invention relates to a synthesis method of analgesic intermediate bromomethyl cyclobutane. The synthesis method comprises the following steps: by taking ethylene and acrylic acid as starting materials, carrying out Diels-Alder reaction to obtain cyclobutanecarboxylic acid, then reducing to obtain cyclobutanemethanol, and then brominating to obtain high-purity bromomethyl cyclobutane, wherein the total yield reaches more than 65%. The synthesis method provided by the invention has the advantages of available raw materials, mild reaction conditions, simple postprocessing operation, small environmental pollution, short reaction time, high reaction operational safety, high reaction yield, good product quality and low cost, and industrial production is facilitated.

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