isolaureatin

Base Information

• Chemical Name: isolaureatin
• CAS No.: 19897-64-4
• Molecular Formula: C15H20Br2O2
• Molecular Weight: 392.1261
• NSC Number: 122225
• Nikkaji Number: J13.598D
• Mol file: 19897-64-4.mol

Synonyms:Z-isolaureatin;

Chemical Property of isolaureatin

Chemical Property:

• Vapor Pressure: 4.98E-07mmHg at 25°C
• Melting Point: 83-84 °C
• Boiling Point: 424.8°Cat760mmHg
• Flash Point: 175.9°C
• PSA: 18.46000
• Density: 1.469g/cm³
• LogP: 3.81790
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 391.98096
• Heavy Atom Count: 19
• Complexity: 374

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1CC2C(CC(O2)C(O1)CC=CC#C)Br)Br
• Isomeric SMILES: CCC(C1CC2C(CC(O2)C(O1)C/C=C/C#C)Br)Br

Technology Process of isolaureatin

There total 22 articles about isolaureatin 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: 96.0%

{5-[7-bromo-4-(1-bromo-propyl)-3,9-dioxa-bicyclo[4.2.1]non-2-yl]-pent-3-en-1-ynyl}-triisopropyl-silane (934977-19-2) → (+)-3-(Z)-isolaureatin (19897-64-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -20 ℃; for 1h;

DOI:10.1021/ja068346i

Reference yield:

1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol (934977-35-2) → (+)-3-(Z)-isolaureatin (19897-64-4)

Guidance literature:

Multi-step reaction with 20 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: 98 percent / NaH / tetrahydrofuran / 12 h / 20 °C

9.1: 92 percent / NMO / TPAP / CH₂Cl₂ / 3 h / 20 °C

10.1: KHMDS / toluene; tetrahydrofuran / 0.5 h / -78 °C

10.2: 94 percent / toluene; tetrahydrofuran / 1 h / -78 °C

11.1: lithium chloride / Pd(PPh₃)4 / tetrahydrofuran / 3 h / Heating

11.2: 75 percent / Br₂ / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

12.1: 88 percent / p-toluenesulfonyl hydrazide / xylene / 2 h / 140 °C

13.1: 86 percent / tetrahydrofuran / 1 h / 20 °C

14.1: 75 percent / KOH / tetrahydrofuran; methanol; H₂O / 48 h / 20 °C

15.1: 94 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 0.33 h / -78 °C

16.1: 84 percent / CBr₄; tri-n-octylphosphine / toluene / 4 h / 80 °C

17.1: 97 percent / H₂ / Pd/C / ethanol; ethyl acetate / 2 h

18.1: o-nitrophenylselenocyanide; tri-n-octylphosphine / tetrahydrofuran / 2 h / 20 °C

18.2: 88 percent / m-CPBA / tetrahydrofuran / 0 - 20 °C

19.1: 76 percent / Grubbs second generation catalyst / benzene / 4 h / 50 °C

20.1: 96 percent / TBAF / tetrahydrofuran / 1 h / -20 °C

With tetrachloromethane; potassium hydroxide; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ortho-nitrophenyl selenocyanate; ethanol; carbon tetrabromide; TOP; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; L-Selectride; sodium hydride; toluene-4-sulfonic acid hydrazide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; xylene; benzene;

DOI:10.1021/ja068346i

Reference yield:

2-[1-(3-benzyloxy-propyl)-2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyloxy]-N,N-dimethyl-acetamide (934977-36-3) → (+)-3-(Z)-isolaureatin (19897-64-4)

Guidance literature:

Multi-step reaction with 19 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: 98 percent / NaH / tetrahydrofuran / 12 h / 20 °C

8.1: 92 percent / NMO / TPAP / CH₂Cl₂ / 3 h / 20 °C

9.1: KHMDS / toluene; tetrahydrofuran / 0.5 h / -78 °C

9.2: 94 percent / toluene; tetrahydrofuran / 1 h / -78 °C

10.1: lithium chloride / Pd(PPh₃)4 / tetrahydrofuran / 3 h / Heating

10.2: 75 percent / Br₂ / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

11.1: 88 percent / p-toluenesulfonyl hydrazide / xylene / 2 h / 140 °C

12.1: 86 percent / tetrahydrofuran / 1 h / 20 °C

13.1: 75 percent / KOH / tetrahydrofuran; methanol; H₂O / 48 h / 20 °C

14.1: 94 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 0.33 h / -78 °C

15.1: 84 percent / CBr₄; tri-n-octylphosphine / toluene / 4 h / 80 °C

16.1: 97 percent / H₂ / Pd/C / ethanol; ethyl acetate / 2 h

17.1: o-nitrophenylselenocyanide; tri-n-octylphosphine / tetrahydrofuran / 2 h / 20 °C

17.2: 88 percent / m-CPBA / tetrahydrofuran / 0 - 20 °C

18.1: 76 percent / Grubbs second generation catalyst / benzene / 4 h / 50 °C

19.1: 96 percent / TBAF / tetrahydrofuran / 1 h / -20 °C

With tetrachloromethane; potassium hydroxide; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ortho-nitrophenyl selenocyanate; ethanol; carbon tetrabromide; TOP; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; L-Selectride; sodium hydride; toluene-4-sulfonic acid hydrazide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; xylene; benzene;

DOI:10.1021/ja068346i

upstream raw materials:

{5-[7-bromo-4-(1-bromo-propyl)-3,9-dioxa-bicyclo[4.2.1]non-2-yl]-pent-3-en-1-ynyl}-triisopropyl-silane

2-allyl-7-bromo-4-(1-bromo-propyl)-3,9-dioxa-bicyclo[4.2.1]nonane

3-[7-bromo-4-(1-bromo-propyl)-3,9-dioxa-bicyclo[4.2.1]non-2-yl]-propan-1-ol

2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoic acid methyl ester

Refernces