Strobilurin G

Base Information

• Chemical Name: Strobilurin G
• CAS No.: 129145-64-8
• Molecular Formula: C₂₆H₃₄O₆
• Molecular Weight: 442.552
• Hs Code.: 29419000
• UNII: 49G3784VEO
• ChEMBL ID: CHEMBL4636674
• Mol file: 129145-64-8.mol

Synonyms:3,5-hexadienoic acid, 6-((3S)-3,4-dihydro-4,4-dimethyl-3-((3-methyl-2-butenyl)oxy)-2h-1,5-benzodioxepin-7-yl)-2-(methoxymethylene)-3-methyl-, methyl ester, (2E,3Z,5E)-;strobilurin D;strobilurin G

Chemical Property of Strobilurin G

Chemical Property:

• Vapor Pressure: 3.66E-13mmHg at 25°C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 442.23553880
• Heavy Atom Count: 32
• Complexity: 741

Purity/Quality:

98% ^*data from raw suppliers

STROBILURIN G 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCOC1COC2=C(C=C(C=C2)C=CC=C(C)C(=COC)C(=O)OC)OC1(C)C)C
• Isomeric SMILES: CC(=CCO[C@H]1COC2=C(C=C(C=C2)/C=C/C=C(/C)\C(=C/OC)\C(=O)OC)OC1(C)C)C

Technology Process of Strobilurin G

There total 7 articles about Strobilurin G 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: 38.0%

methyl (Z)-2-tributylstannyl-3-methoxypropenoate + (S)-(1E,3Z)-8-(4-iodopenta-1,3-dienyl)-2,2-dimethyl-3-(3-methyl-2-butenyloxy)-3,4-dihydro-2H-benzo[b][1,4]dioxepin (716305-20-3) → strobilurin G (132056-04-3,129145-64-8)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; at 50 ℃; for 24h;

DOI:10.1016/j.tet.2004.03.092

Reference yield:

prenyl bromide (870-63-3) → strobilurin G (132056-04-3,129145-64-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / NaH / dimethylformamide / 16 h / 0 °C

2.1: 87 percent / DIBAL-H / tetrahydrofuran / 2 h / -78 °C

3.1: 80 percent / MnO₂ / CH₂Cl₂ / 48 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 1 h / -40 °C

4.2: 40 percent / tetrahydrofuran / 2 h / 20 °C

5.1: 63 percent / KI; HMPT; CuI / 48 h / 120 °C

6.1: 38 percent / Pd(PPh₃)4; CuI / 1-methyl-pyrrolidin-2-one / 24 h / 50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium hydride; diisobutylaluminium hydride; potassium iodide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; N,N-dimethyl-formamide; 4.2: Wittig reaction / 6.1: Stille cross-coupling reaction;

DOI:10.1016/j.tet.2004.03.092

Reference yield:

ethyl (S)-3-(3-hydroxy-4,4-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)acrylate (247922-50-5) → strobilurin G (132056-04-3,129145-64-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / NaH / dimethylformamide / 16 h / 0 °C

2.1: 87 percent / DIBAL-H / tetrahydrofuran / 2 h / -78 °C

3.1: 80 percent / MnO₂ / CH₂Cl₂ / 48 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 1 h / -40 °C

4.2: 40 percent / tetrahydrofuran / 2 h / 20 °C

5.1: 63 percent / KI; HMPT; CuI / 48 h / 120 °C

6.1: 38 percent / Pd(PPh₃)4; CuI / 1-methyl-pyrrolidin-2-one / 24 h / 50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium hydride; diisobutylaluminium hydride; potassium iodide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; N,N-dimethyl-formamide; 4.2: Wittig reaction / 6.1: Stille cross-coupling reaction;

DOI:10.1016/j.tet.2004.03.092

upstream raw materials:

(S)-(1E,3Z)-8-(4-iodopenta-1,3-dienyl)-2,2-dimethyl-3-(3-methyl-2-butenyloxy)-3,4-dihydro-2H-benzo[b][1,4]dioxepin

prenyl bromide

ethyl (S)-3-(3-hydroxy-4,4-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)acrylate

(S)-3-{4,4-dimethyl-3-(3-methylbut-2-enyloxy)-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl}propenal

Refernces