29-Methylidene-2,3-oxidosqualene

Base Information

• Chemical Name: 29-Methylidene-2,3-oxidosqualene
• CAS No.: 145919-42-2
• Molecular Formula: C₃₁H₅₀O
• Molecular Weight: 438.737
• Wikidata: Q27071878
• Pharos Ligand ID: 5RG4GPATT49N
• Mol file: 145919-42-2.mol

Synonyms:(3H)29-MOS;29-methylidene-2,3-oxidosqualene;29-MOS

Chemical Property of 29-Methylidene-2,3-oxidosqualene

Chemical Property:

• Vapor Pressure: 2.9E-10mmHg at 25°C
• Boiling Point: 516.5°Cat760mmHg
• Flash Point: 251.8°C
• PSA: 12.53000
• Density: 0.885g/cm³
• LogP: 9.98230
• XLogP3: 10.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 17
• Exact Mass: 438.386166214
• Heavy Atom Count: 32
• Complexity: 696

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CCCC(=CCCC(=CCCC=C(C)CCC=C(C)CCC1C(O1)(C)C)C)CC=C
• Isomeric SMILES: C/C=C\CC/C(=C\CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/CC=C

Technology Process of 29-Methylidene-2,3-oxidosqualene

There total 56 articles about 29-Methylidene-2,3-oxidosqualene 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:

(4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-al (56882-09-8) → (6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene (137846-76-5,145919-42-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / p-TsOH*H₂O / benzene / 4 h / Heating

2: 41 percent / aq. NBS / tetrahydrofuran / 0.25 h / 0 °C

3: 72 percent / PdCl₂(CH₃CN)2 / acetone / 8 h

4: 73 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

5: 1.) 18-crown-6, <(CH₃)3Si>2NK / 1.) THF, toluene, -80 deg C, 30 min, 2.) THF, toluene, a) -80 deg C, 2 h, b) -40 deg C, 15 min

6: 94 percent / LiAlH₄ / diethyl ether / 0.5 h / -30 °C

7: 88 percent / Na₂CO₃, MnO₂ / hexane / 4 h / 5 °C

8: 1.) n-BuLi / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, hexane, a) -80 deg C, 30 min, b) RT, 30 min

With manganese(IV) oxide; dichloro bis(acetonitrile) palladium(II); N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; potassium hexamethylsilazane; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; acetone; benzene;

DOI:10.1021/jm970534j

Reference yield:

(2Z,6E,10E,14E)-18,19-epoxy-6,11,15,19-tetramethyl-2-(4-methyl-3-pentenyl)-2,6,10,14-icosatetraen-1-ol (137846-80-1) → (6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene (137846-76-5,145919-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / Na₂CO₃, MnO₂ / hexane / 4 h / 5 °C

2: 1.) n-BuLi / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, hexane, a) -80 deg C, 30 min, b) RT, 30 min

With manganese(IV) oxide; n-butyllithium; sodium carbonate; In hexane;

DOI:10.1021/jm970534j

Reference yield:

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4) → (6Z,10E,14E,18E)-22,23-epoxy-2,10,15,19,23-pentamethyl-6-vinyl-2,6,10,14,18-tetracosapentaene (137846-76-5,145919-42-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / H₅IO₆ / tetrahydrofuran; H₂O / 10 h / 0 - 20 °C

2: 96 percent / KN(TMS)2, 18-crown-6- / 2 h / -78 °C

3: LiAlH₄ / 1 h / 0 °C

4: 11 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 3 h / 0 °C

5: K₂CO₃ / methanol / 0.5 h / 20 °C

6: MnO₂, Na₂CO₃ / hexane / 35 h / 20 °C

7: 1 h / -78 - 0 °C

With manganese(IV) oxide; N-Bromosuccinimide; lithium aluminium tetrahydride; 18-crown-6 ether; potassium hexamethylsilazane; sodium carbonate; potassium carbonate; periodic acid; In tetrahydrofuran; methanol; hexane; water;

DOI:10.1021/ja00025a043

upstream raw materials:

(2Z,6E,10E,14E)-17-(3,3-Dimethyl-oxiranyl)-6,11,15-trimethyl-2-(4-methyl-pent-3-enyl)-heptadeca-2,6,10,14-tetraenal

Methylenetriphenylphosphorane

Methyltriphenylphosphonium bromide

5-iodo-2-methylpent-2-ene

Refernces

• 1、 Ceruti, Maurizio,Rocco, Flavio,Viola, Franca,Balliano, Gianni,Milla, Paola,Arpicco, Silvia,Cattel, Luigi. "29-Methylidene-2,3-oxidosqualene derivatives as stereospecific mechanism-based inhibitors of liver and yeast oxidosqualene cyclase". . p. 540 - 554. Retrieved 2007/10/03.
• 2、 Xiao, Xiao-yi,Prestwich, Glenn D.. "29-Methylidene-2,3-oxidosqualene: A Potent Mechanism-Based Inactivator of Oxidosqualene Cyclase". . p. 9673 - 9674. Retrieved 2007/10/02.