140200-76-6

Basic information

• Product Name: 1,5-DIBROMO-PENTAN-3-ONE
• Synonyms: 1,5-DIBROMO-PENTAN-3-ONE;1,5-DibroMo-3-pentanone;3-Pentanone, 1,5-dibroMo-
• CAS NO: 140200-76-6
• Molecular Formula: C₅H₈Br₂O
• Molecular Weight: 243.92442
• Mol File: 140200-76-6.mol

Chemical Properties

• Melting Point: 89.7-90.5 °C
• Boiling Point: 259.1°C at 760 mmHg
• Flash Point: 101.269°C
• Appearance: /
• Density: 1.813g/cm³
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: 1,5-DIBROMO-PENTAN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIBROMO-PENTAN-3-ONE(140200-76-6)
• EPA Substance Registry System: 1,5-DIBROMO-PENTAN-3-ONE(140200-76-6)

Safety Data

• Hazardous Substances Data: 140200-76-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,5-Dibromo-pentan-3-one is used as a reagent in organic synthesis for the preparation of various compounds, leveraging its bromine atoms to facilitate chemical reactions and the formation of new products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,5-Dibromo-pentan-3-one serves as a key intermediate in the synthesis of biologically active compounds, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Industry:
This chemical compound is utilized in the chemical industry for the production of a variety of products, taking advantage of its brominating properties to enhance the functionality of other chemicals.
Used as a Pesticide:
1,5-Dibromo-pentan-3-one is employed as a pesticide, capitalizing on its ability to control, repel, or kill pests, thereby protecting crops and enhancing agricultural yields.
Used as a Solvent:
It can also function as a solvent in certain applications, where its unique properties allow for the dissolution of specific substances that are otherwise difficult to process.

InChI:InChI=1/C5H8Br2O/c6-3-1-5(8)2-4-7/h1-4H2

Synthetic route

1-(2-bromoethyl)cyclopropan-1-ol (128312-82-3) → α,α'-dibromopentan-3-one (140200-76-6)

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane at 20℃; for 2h;	81%
With N-Bromosuccinimide In tetrachloromethane for 14h; Reflux;	77%
With N-Bromosuccinimide In tetrachloromethane at 0 - 25℃; for 16h;	68%

α,α'-dibromopentan-3-one (140200-76-6) → divinylketone (1890-28-4)

Conditions	Yield
With triethylamine In dichloromethane for 19h;	93%
With sodium carbonate under 65 - 80 Torr; Heating;	78%

ethylene glycol (107-21-1) + α,α'-dibromopentan-3-one (140200-76-6) → 1,5-Dibromopentan-3-one ethylene ketal (164987-79-5)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 24h; Heating;	86%
With pyridinium p-toluenesulfonate; orthoformic acid triethyl ester at 20℃; for 18h;	32%

(S)-2-amino-1-(phenanthridin-5(6H)-yl)propan-1-one (1613244-28-2) + α,α'-dibromopentan-3-one (140200-76-6) → (S)-1-(1-oxo-1-(phenanthridin-5(6H)-yl)propan-2-yl)piperidin-4-one (1613244-29-3)

Conditions	Yield
With sodium hydrogencarbonate In methanol at 60℃; for 0.5h; Reflux;	75%

α,α'-dibromopentan-3-one (140200-76-6) → Tetrahydrothiopyran-4-one (1072-72-6)

Conditions	Yield
With sodium sulfide In methanol for 1h; Heating;	71%

α,α'-dibromopentan-3-one (140200-76-6) → 1,5-dibromopentane-3-ol

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 25℃; for 3h;	67%

3-(2-cyclopropyl-4-iodo-1H-imidazol-1-yl)bicyclo[1.1.1]pentan-1-amine bis(2,2,2-trifluoroacetate) + α,α'-dibromopentan-3-one (140200-76-6) → 1-(3-(2-cyclopropyl-4-iodo-1H-imidazol-1-yl)bicyclo[1.1.1]pentan-1-yl)piperidin-4-one

Conditions	Yield
With potassium carbonate In acetonitrile at 75℃; for 16h;	56%

α,α'-dibromopentan-3-one (140200-76-6) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2,2-bis(2-bromoethyl)-5,5-dimethyl-1,3-dioxane (187850-33-5) + 2-(2-bromoethyl)-5,5-dimethyl-2-ethenyl-1,3-dioxane (187850-34-6)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 60h; Heating;	A 22% B 50%

α,α'-dibromopentan-3-one (140200-76-6) + furfuryl alcohol α-(tributylstannyl)methyl ether (167106-10-7) → (1S*,2S*,3S*,4S*,7R*)-2,4-dimethyl-9-oxabicyclo<5.3.0>dec-5-en-1,3-diol

Conditions	Yield
With methyllithium; silver; L-Selectride; zinc 2.) THF, 195 K; 3.) THF, 195 K to 273 K, 2 h; Yield given. Multistep reaction;

α,α'-dibromopentan-3-one (140200-76-6) → 2-(2-bromoethyl)-5,5-dimethyl-2-ethenyl-1,3-dioxane (187850-34-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → 5,5-dimethyl-2-ethenyl-2-(2-iodoethyl)-1,3-dioxane (187850-35-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (3aS,7aR)-3a-(3,4-Dimethoxy-phenyl)-1-methyl-7-methylene-octahydro-indol-6-one

Conditions	Yield
Multi-step reaction with 10 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 6: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 7: 0.870 g / benzene / 1 h / Heating 8: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 9: 2) H2 / 2) Raney nickel / 1) methanol, RT, 10 min, 2) 48 h 10: 55 percent / aq. TFA / 8 h / Ambient temperature View Scheme
Multi-step reaction with 9 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 5: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 6: 0.870 g / benzene / 1 h / Heating 7: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 8: 2) H2 / 2) Raney nickel / 1) methanol, RT, 10 min, 2) 48 h 9: 55 percent / aq. TFA / 8 h / Ambient temperature View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (+)-[(3aS,7R,7aS)-3a-(3,4-dimethoxyphenyl)-6,6-(2,2-dimethylpropylenedioxy)octahydroindol-7-yl]methanol (187850-40-4)

Conditions	Yield
Multi-step reaction with 8 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 6: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 7: 0.870 g / benzene / 1 h / Heating 8: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature View Scheme
Multi-step reaction with 7 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 5: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 6: 0.870 g / benzene / 1 h / Heating 7: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (+)-(3aS,7R,7aS)-[3a-(3,4-dimethoxyphenyl)-6,6-(2,2-dimethylpropylenedioxy)-1-methyloctahydroindol-7-yl]methanol (187850-43-7)

Conditions	Yield
Multi-step reaction with 9 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 6: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 7: 0.870 g / benzene / 1 h / Heating 8: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 9: 2) H2 / 2) Raney nickel / 1) methanol, RT, 10 min, 2) 48 h View Scheme
Multi-step reaction with 8 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 5: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 6: 0.870 g / benzene / 1 h / Heating 7: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 8: 2) H2 / 2) Raney nickel / 1) methanol, RT, 10 min, 2) 48 h View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (+)-(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-6-[(2,2-dimethyl-3-hydroxypropyl)oxy]-7-formyl-2,3,3a,4,5,7a-hexahydro-6H-indole (187850-45-9)

Conditions	Yield
Multi-step reaction with 10 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 6: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 7: 0.870 g / benzene / 1 h / Heating 8: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 9: 2) H2 / 2) Raney nickel / 1) methanol, RT, 10 min, 2) 48 h 10: 1) tert-butyl alcohol, ethylmagnesium bromide, 2) 1,1'-(azodicarbonyl)dipiperidine / 1) THF, 10 min, 2) RT, 2.5 h View Scheme
Multi-step reaction with 9 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 5: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 6: 0.870 g / benzene / 1 h / Heating 7: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 8: 2) H2 / 2) Raney nickel / 1) methanol, RT, 10 min, 2) 48 h 9: 1) tert-butyl alcohol, ethylmagnesium bromide, 2) 1,1'-(azodicarbonyl)dipiperidine / 1) THF, 10 min, 2) RT, 2.5 h View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (+)-(3aR,6aS,6bS)-6a-(3,4-dimethoxyphenyl)-4,4-(2,2-dimethylpropylenedioxy)perhydropyrrolo(3,2,1-ij)benzoxazine

Conditions	Yield
Multi-step reaction with 9 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 6: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 7: 0.870 g / benzene / 1 h / Heating 8: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 9: 70 percent / methanol; H2O / 1 h / Ambient temperature View Scheme
Multi-step reaction with 8 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 5: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 6: 0.870 g / benzene / 1 h / Heating 7: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 8: 70 percent / methanol; H2O / 1 h / Ambient temperature View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → 2-[3-(3,4-Dimethoxy-phenyl)-4-nitro-4-phenylselanyl-butyl]-5,5-dimethyl-2-vinyl-[1,3]dioxane (187850-36-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (+)-{(3aS,7R,7aS)-3a-(3,4-dimethoxyphenyl)-6,6-(2,2-dimethylpropylenedioxy)-1-[(4-methylphenyl)sulfonyl]-octahydroindol-7-yl}methanol

Conditions	Yield
Multi-step reaction with 9 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 6: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 7: 0.870 g / benzene / 1 h / Heating 8: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 9: 89 percent / triethylamine / CH2Cl2 / 1 h / 0 °C View Scheme
Multi-step reaction with 8 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 5: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 6: 0.870 g / benzene / 1 h / Heating 7: 74 percent / H2 / Raney nickel / methanol / 48 h / 15514.4 Torr / Ambient temperature 8: 89 percent / triethylamine / CH2Cl2 / 1 h / 0 °C View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (+)-(5S,6aS,9aR,9bS)-9,9-(2,2-Dimethylpropylenedioxy)-6a-(3,4-dimethoxyphenyl)-5-{[(1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexyl]oxy}hexahydro-1H-isooxazolo-[2,3,3-h] [2,1]benzoxazine (187850-39-1)

Conditions	Yield
Multi-step reaction with 7 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 6: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 7: 0.870 g / benzene / 1 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 5: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C 6: 0.870 g / benzene / 1 h / Heating View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (4S,6S)-4-{5-[3,3-(2,2-Dimethylpropylenedioxy)-1-pentenyl]}-4-(3,4-dimethoxyphenyl)-6-{[(1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexyl]oxy}-5,6-dihydro-4H-[1,2]oxazine N-Oxide (187850-38-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 6: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C View Scheme
Multi-step reaction with 5 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature 5: trimethylaluminium, 2,6-di-tert-butyl-4-methylphenol / toluene; CH2Cl2 / -15 °C View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → 2-{4-[2-(3,4-Dimethoxyphenyl)-1-nitro-1-butenyl]}-2-ethenyl-5,5-dimethyl-1,3-dioxane (909196-62-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → 2-[(E)-3-(3,4-Dimethoxy-phenyl)-4-nitro-but-3-enyl]-5,5-dimethyl-2-vinyl-[1,3]dioxane

Conditions	Yield
Multi-step reaction with 5 steps 1: 22 percent / TsOH*H2O / benzene / 60 h / Heating 2: 58 percent / TsOH*H2O / benzene / 60 h / Heating 3: 89 percent / NaI / acetone / 26 h / Heating 5: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 50 percent / TsOH*H2O / benzene / 60 h / Heating 2: 89 percent / NaI / acetone / 26 h / Heating 4: aq. H2O2 / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (S)-2-(4,4-dimethoxypiperidin-1-yl)-1-(phenanthridin-5(6H)-yl)propan-1-one (1613244-30-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / methanol / 0.5 h / 60 °C / Reflux 2: toluene-4-sulfonic acid / methanol / 8 h / 0 - 20 °C View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → (S)-1-cinnamyl-4,4-dimethoxy-1-(1-oxo-1-(phenanthridin-5(6H)-yl)propan-2-yl)piperidin-1-iumbromide

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / methanol / 0.5 h / 60 °C / Reflux 2: toluene-4-sulfonic acid / methanol / 8 h / 0 - 20 °C 3: acetonitrile / 60 h / 20 °C View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → 1-bromo-5-((3-ethoxybenzo[d]isoxazole-6-yl)oxy)pentyl-3-ol

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; sodium tetrahydroborate / 3 h / 0 - 25 °C 2: potassium iodide / acetone / 16 h / 60 °C View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → 2-(5-((3-ethoxybenzo[d]isoxazole-6-yl)oxy)-3-hydroxypentyl)-5-(pyridin-4-yl)-1,2,5-thiadiazolidine-1,1-dioxide

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol; sodium tetrahydroborate / 3 h / 0 - 25 °C 2: potassium iodide / acetone / 16 h / 60 °C 3: potassium iodide / N,N-dimethyl-formamide / 3 h / 60 °C View Scheme

α,α'-dibromopentan-3-one (140200-76-6) → 2-(5-((3-ethoxybenzo[d]isoxazole-6-yl)oxy)-3-fluoropentyl)-5-(pyridin-4-yl)-1,2,5-thiadiazolidine-1,1-dioxide

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol; sodium tetrahydroborate / 3 h / 0 - 25 °C 2: potassium iodide / acetone / 16 h / 60 °C 3: potassium iodide / N,N-dimethyl-formamide / 3 h / 60 °C 4: diethylamino-sulfur trifluoride / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere View Scheme

α,α'-dibromopentan-3-one (140200-76-6) + aniline (62-53-3) → 1-phenyl-2,3-dihydropyridin-4(1H)-one (35487-96-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 80 °C / Inert atmosphere 2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; pentafluoronitrobenzen; potassium acetate / dichloromethane / 96 h / 35 °C / Inert atmosphere; Irradiation View Scheme

α,α'-dibromopentan-3-one (140200-76-6) + aniline (62-53-3) → 1-phenylpiperidin-4-one (19125-34-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;

Methyltriphenylphosphonium bromide (1779-49-3) + α,α'-dibromopentan-3-one (140200-76-6) → 1,5-dibromo-3-methylene pentane

Conditions	Yield
With potassium tert-butylate In acetonitrile at 0 - 10℃; Solvent; Inert atmosphere;

Upstream product

• 128312-82-3 1-(2-bromoethyl)cyclopropan-1-ol 

Downstream Products

• 1072-72-6 Tetrahydrothiopyran-4-one 
• 1890-28-4 divinylketone 
• 1613244-30-6 (S)-2-(4,4-dimethoxypiperidin-1-yl)-1-(phenanthridin-5(6H)-yl)propan-1-one 
• 35487-96-8 1-phenyl-2,3-dihydropyridin-4(1H)-one 
• 19125-34-9 1-phenylpiperidin-4-one 
• 3522-98-3 4-methylenepiperidine hydrobromide 
• 148133-82-8 4-methylene piperidine 
• 909196-62-9 2-{4-[2-(3,4-Dimethoxyphenyl)-1-nitro-1-butenyl]}-2-ethenyl-5,5-dimethyl-1,3-dioxane 
• 187850-38-0 (4S,6S)-4-{5-[3,3-(2,2-Dimethylpropylenedioxy)-1-pentenyl]}-4-(3,4-dimethoxyphenyl)-6-{[(1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexyl]oxy}-5,6-dihydro-4H-[1,2]oxazine N-Oxide 
• 187850-39-1 (+)-(5S,6aS,9aR,9bS)-9,9-(2,2-Dimethylpropylenedioxy)-6a-(3,4-dimethoxyphenyl)-5-{[(1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexyl]oxy}hexahydro-1H-isooxazolo-[2,3,3-h] [2,1]benzoxazine 
• 187850-36-8 2-[3-(3,4-Dimethoxy-phenyl)-4-nitro-4-phenylselanyl-butyl]-5,5-dimethyl-2-vinyl-[1,3]dioxane 
• 187850-45-9 (+)-(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-6-[(2,2-dimethyl-3-hydroxypropyl)oxy]-7-formyl-2,3,3a,4,5,7a-hexahydro-6H-indole 
• 187850-43-7 (+)-(3aS,7R,7aS)-[3a-(3,4-dimethoxyphenyl)-6,6-(2,2-dimethylpropylenedioxy)-1-methyloctahydroindol-7-yl]methanol 
• 187850-40-4 (+)-[(3aS,7R,7aS)-3a-(3,4-dimethoxyphenyl)-6,6-(2,2-dimethylpropylenedioxy)octahydroindol-7-yl]methanol 

Relevant articles and documents

ANTI-ENTEROVIRUS 71 THIADIAZOLIDINE DERIVATIVE

Disclosed is a novel anti-enterovirus 71 (EV71) 1,2,5-thiadiazolidine-1,1-dioxide derivative or a pharmaceutically acceptable salt thereof; and specifically, a compound represented by formula (II) or a pharmaceutically acceptable salt thereof.

Double axial chirality promoted asymmetric [2,3] Stevens rearrangement of N-cinnamyl l-alanine amide-derived ammonium ylides

The base-induced asymmetric [2,3] Stevens rearrangement of N-cinnamyl tetraalkylammonium ylides derived from l-alanine amides proceeds via a double axially chiral intermediate to afford the corresponding α-substituted alanine derivatives with high enantio- and diastereoselectivities. the Partner Organisations 2014.

4'-AMINO CYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): formula (I) wherein Cy is selected from formula (Il) and wherein R1, R2, R3, Q, G, Ar, m, n and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

Ruthenium-lewis acid catalyzed asymmetric diels-alder reactions between dienes and α,β-unsaturated ketones

The complex [Ru(Cp)(R,R-BIPHOP-F)(acetone)][SbF6],(R,R)-1a. was used as catalyst for asymmetric Diels-Alder reactions between dienes (cyclopentadiene, methylcyclopentadienc, isoprene, 2,3-dimethylbutadiene) and α,β-unsaturated ketones (methyl vinyl ketone (MVK). ethyl vinyl ketone, divinyl ketone, α-bromovinyl methyl ketone and α-chlorovinyl methyl ketone). The cycloaddition products were obtained in yields of 50-_90% and with enantioselectivities up to 96% ee. Ethyl vinyl ketone, divinyl ketone and the halogenated vinyl ketones worked best and their reactions with acyclic dienes consistently provided products with >90% ee. α-Chlorovinyl methyl ketone performed better than α-bromovinyl methyl ketone. The reaction also provided a [4.3.1]bicyclic ring system in 95% ee through an intramolecular cycloaddition reaction. Crystal structure determinations of [Ru(Cp)((S,S)-BIPHOP-F)(mvk)]-[SbF6], (S,S)-1b, and [Ru(Cp)((R,R)-Me4BIPHOP-F)(acrolein)][SbF6], (R,R)-2b, provided the basis for a rationalization of the asymmetric induction.

Asymmetric construction of a quaternary carbon center by tandem [4 + 2]/[3 + 2] cycloaddition of a nitroalkene. The total synthesis of (-)-mesembrine

An efficient, total synthesis of the Sceletium alkaloid (-)-mesembrine is accomplished in seven steps and 19% yield from a functionalized nitroalkene (itself prepared in six steps and 34% yield from ethyl 3-bromopropionate). The construction of the octahydroindole framework of mesembrine features a tandem inter [4 + 2]/intra [3 + 2] cycloaddition of a 2,2-disubstituted 1-nitroalkene and a chiral vinyl ether derived from (1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexanol as the central strategic element. The two stereogenic centers of the natural product, which include a benzylic, quaternary center, were established in 26/1 selectivity in the tandem process.

A SIMPLE METHOD FOR THE PRODUCTION OF 1,5-DIHALOGENO-3-PENTANONES AND 1-BROMO-3-PENTANONE - PRECURSORS OF DIVINYL AND ETHYL VINYL KETONES

The reaction of methyl 3-halogenopropionates with ethylmagnesium bromide in the presence of catalytic amounts of tetraisopropoxytitanium gave the corresponding 1-(2-halogenoethyl)cyclopropanols, the bromination of which with N-bromosuccinimide led to high yields of 1,5-dihalogeno-3-pentanones. 1-Bromo-3-pentanone was obtained by the acid-catalyzed opening of the three-membered ring of 1-(2-bromoethyl)cyclopropanol and also by the bromination of 1-ethylcyclopropanol.The reactions of 1,5-dibromo-3-pentanone with sodium carbonate and sodium sulfide led to good yields of divinyl ketone and 4-tetrahydrothiopyrone respectively.