1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one

Base Information

Chemical Name:1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one
CAS No.:934977-20-5
Molecular Formula:C₂₀H₂₇BrO₄
Molecular Weight:411.336
Hs Code.:

Synonyms:1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one

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Chemical Property of 1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one

Chemical Property:

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Technology Process of 1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one

There total 14 articles about 1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one 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:

: 934977-36-3
2-[1-(3-benzyloxy-propyl)-2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyloxy]-N,N-dimethyl-acetamide

: 934977-20-5
1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 97 percent / ethanol / PTSA / 3 h / 20 °C

2.1: 92 percent / Ph₃P; CCl₄ / 2 h / Heating

3.1: 89 percent / KHMDS / toluene / 0.5 h / 20 °C

4.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

5.1: CCl₄; 1-methylcyclohexene; tri-n-octylphosphine / toluene / 12 h / 70 °C

6.1: 430.0 mg / NMO / OsO₄ / acetone; H₂O / 4 h / 0 °C

7.1: dibutyltin oxide / toluene / 2 h / Heating

7.2: 80 percent / TBAI / toluene / 1 h / Heating

8.1: 90 percent / NaH / dimethylformamide / 12 h / 20 °C

9.1: 96 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C / pH 7.0 / buffered reaction

10.1: CBr₄; tri-n-octylphosphine; pyridine / toluene / 12 h / 80 °C

11.1: tetrahydrofuran / 1 h / 20 °C

With pyridine; tetrachloromethane; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ethanol; carbon tetrabromide; TOP; potassium hexamethylsilazane; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja068346i

Reference yield:

: 934977-35-2
1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol

: 934977-20-5
1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

1.2: 100 percent / tetrahydrofuran / 4 h / 20 °C

2.1: 97 percent / ethanol / PTSA / 3 h / 20 °C

3.1: 92 percent / Ph₃P; CCl₄ / 2 h / Heating

4.1: 89 percent / KHMDS / toluene / 0.5 h / 20 °C

5.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

6.1: CCl₄; 1-methylcyclohexene; tri-n-octylphosphine / toluene / 12 h / 70 °C

7.1: 430.0 mg / NMO / OsO₄ / acetone; H₂O / 4 h / 0 °C

8.1: dibutyltin oxide / toluene / 2 h / Heating

8.2: 80 percent / TBAI / toluene / 1 h / Heating

9.1: 90 percent / NaH / dimethylformamide / 12 h / 20 °C

10.1: 96 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C / pH 7.0 / buffered reaction

11.1: CBr₄; tri-n-octylphosphine; pyridine / toluene / 12 h / 80 °C

12.1: tetrahydrofuran / 1 h / 20 °C

With pyridine; tetrachloromethane; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ethanol; carbon tetrabromide; TOP; potassium hexamethylsilazane; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja068346i

Reference yield:

: 183312-54-1
3-benzyloxypropylmagnesium bromide

: 934977-20-5
1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: DIBAL-H / diethyl ether; hexane / 0.5 h / -78 - 20 °C

1.2: 87 percent / diethyl ether; hexane / 12 h / -30 - -20 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 100 percent / tetrahydrofuran / 4 h / 20 °C

3.1: 97 percent / ethanol / PTSA / 3 h / 20 °C

4.1: 92 percent / Ph₃P; CCl₄ / 2 h / Heating

5.1: 89 percent / KHMDS / toluene / 0.5 h / 20 °C

6.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

7.1: CCl₄; 1-methylcyclohexene; tri-n-octylphosphine / toluene / 12 h / 70 °C

8.1: 430.0 mg / NMO / OsO₄ / acetone; H₂O / 4 h / 0 °C

9.1: dibutyltin oxide / toluene / 2 h / Heating

9.2: 80 percent / TBAI / toluene / 1 h / Heating

10.1: 90 percent / NaH / dimethylformamide / 12 h / 20 °C

11.1: 96 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C / pH 7.0 / buffered reaction

12.1: CBr₄; tri-n-octylphosphine; pyridine / toluene / 12 h / 80 °C

13.1: tetrahydrofuran / 1 h / 20 °C

With pyridine; tetrachloromethane; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ethanol; carbon tetrabromide; TOP; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja068346i