(E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid

Base Information

• Chemical Name: (E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid
• CAS No.: 20257-75-4
• Molecular Formula: C20H32O2
• Molecular Weight: 304.47
• UNII: 6LTQ2LP2NB
• DSSTox Substance ID: DTXSID701316809
• Nikkaji Number: J15.771F,J3.273.897D
• Wikidata: Q104254224
• Metabolomics Workbench ID: 121250
• ChEMBL ID: CHEMBL102201
• Mol file: 20257-75-4.mol

Synonyms:2-Pentenoic acid,5-(decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl)-3-methyl-,(1R-(1alpha(E),4aalpha,8abeta));

Chemical Property of (E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid

Chemical Property:

• PSA: 37.30000
• LogP: 5.59630
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 304.240230259
• Heavy Atom Count: 22
• Complexity: 486

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCCC2(C)C)C
• Isomeric SMILES: C/C(=C\C(=O)O)/CC[C@@H]1C(=C)CC[C@H]2[C@]1(CCCC2(C)C)C

Technology Process of (E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid

There total 18 articles about (E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid 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: 85.0%

methyl ent-labda-8(17),13-E-dien-15-oate, methyl copalate (10395-37-6,13902-79-9,16633-28-6,17110-88-2,30801-12-8,67010-58-6,110662-53-8) → 5-(2-methylene-5,5,8a-trimethyl-(1R,4aR,8aR)-decahydronaphthalen-1-yl)-3-methylpent-2E-enoic acid (20257-75-4)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2015.12.022

Reference yield:

C21H35NO5 → 5-(2-methylene-5,5,8a-trimethyl-(1R,4aR,8aR)-decahydronaphthalen-1-yl)-3-methylpent-2E-enoic acid (20257-75-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: acetic anhydride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

1.2: 5.67 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / chloroform; isopropyl alcohol / 20 °C / Inert atmosphere

3.1: potassium hydroxide / tetrahydrofuran; water / 20 °C / Inert atmosphere

3.2: 1.17 h / 0 °C / Inert atmosphere

4.1: sulfuric acid / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

5.1: dmap / toluene / 3 h / 90 - 100 °C / Inert atmosphere

6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 5 h / 120 °C / Inert atmosphere

7.1: dmap / tetrahydrofuran / 2 h / Reflux; Inert atmosphere

8.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 3 h / 100 °C / Inert atmosphere

9.1: sodium hydride / tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere; Cooling with ice

9.2: 24 h / 20 °C / Inert atmosphere

10.1: sodium hydroxide / water; ethanol / 3 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; acetic anhydride; sodium hydride; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; isopropyl alcohol; toluene; 3.1: |Nef Reaction / 9.1: |Horner-Wadsworth-Emmons Olefination / 9.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.tet.2015.12.022

Reference yield:

C21H34O3 → 5-(2-methylene-5,5,8a-trimethyl-(1R,4aR,8aR)-decahydronaphthalen-1-yl)-3-methylpent-2E-enoic acid (20257-75-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sulfuric acid / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

2.1: dmap / toluene / 3 h / 90 - 100 °C / Inert atmosphere

2.2: 5 h / 120 °C / Inert atmosphere

3.1: dmap / tetrahydrofuran / 2 h / Reflux; Inert atmosphere

3.2: 3 h / 100 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere; Cooling with ice

4.2: 24 h / 20 °C / Inert atmosphere

5.1: sodium hydroxide / water; ethanol / 3 h / 20 °C / Inert atmosphere

With dmap; sulfuric acid; sodium hydride; sodium hydroxide; In tetrahydrofuran; ethanol; water; toluene; 2.1: |Barton-McCombie Deoxygenation / 2.2: |Barton-McCombie Deoxygenation / 3.1: |Barton-McCombie Deoxygenation / 3.2: |Barton-McCombie Deoxygenation / 4.1: |Horner-Wadsworth-Emmons Olefination / 4.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.tet.2015.12.022

upstream raw materials:

(+/-)-Labda-8(20),13-dien-15-oic acid

methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate

2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)acetaldehyde

3α-hydroxy-13-oxo-15,16-dinor-ent-labda-8(17)-ene

Downstream raw materials:

methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate