Ambreinolide

Base Information

• Chemical Name: Ambreinolide
• CAS No.: 468-84-8
• Deprecated CAS: 21288-58-4
• Molecular Formula: C17H28 O2
• Molecular Weight: 264.408
• European Community (EC) Number: 207-413-7
• UNII: 8M8TY60818
• DSSTox Substance ID: DTXSID10883386
• Nikkaji Number: J41.436K
• Wikidata: Q27896558
• Mol file: 468-84-8.mol

Synonyms:Ambreinolide;Ambreinolid;(+)-Ambreinolide;468-84-8;8M8TY60818;3H-Naphtho(2,1-b)pyran-3-one, dodecahydro-4a,7,7,10a-tetramethyl-, (4aR,6aS,10aS,10bR)-;3H-Naphtho[2,1-b]pyran-3-one, dodecahydro-4a,7,7,10a-tetramethyl-, (4aR,6aS,10aS,10bR)-;EINECS 207-413-7;AMBREINOLIDE, (+)-;SCHEMBL5148266;UNII-8M8TY60818;DTXSID10883386;3H-Naphtho(2,1-b)pyran-3-one, dodecahydro-4a,7,7,10a-tetramethyl-, (4aR-(4aalpha,6abeta,10aalpha,10bbeta))-;Q27896558;14,15,16-Trinorlabdan-13-oic acid, 8-hydroxy-, .delta.-lactone;14,15,16-Trinorlabdan-13-oic acid, 8-hydroxy-, delta-lactone;1-Naphthalenepropionic acid, decahydro-2-hydroxy-2,5,5,8a-tetramethyl-,delta-lactone;(4AR,6AS,10AS,10BR)-DODECAHYDRO-4A,7,7,10A-TETRAMETHYL-3H-NAPHTHO(2,1-B)PYRAN-3-ONE;(4AR-(4aalpha,6abeta,10aalpha,10bbeta))-dodecahydro-4a,7,7,10a-tetramethyl-3H-naphth(2,1-b)pyran-3-one;1-NAPHTHALENEPROPIONIC ACID, DECAHYDRO-2-HYDROXY-2,5,5,8A-TETRAMETHYL-, .DELTA.-LACTONE;3H-NAPHTHO(2,1-B)PYRAN-3-ONE, DODECAHYDRO-4A,7,7,10A-TETRAMETHYL-, (4AR-(4A.ALPHA.,6A.BETA.,10A.ALPHA.,10B.BETA.))-

Chemical Property of Ambreinolide

Chemical Property:

• Boiling Point: 335.5°Cat760mmHg
• Flash Point: 139°C
• Density: 0.994g/cm³
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 264.208930132
• Heavy Atom Count: 19
• Complexity: 400

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3(C2CCC(=O)O3)C)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CCC(=O)O3)C)(C)C

Technology Process of Ambreinolide

There total 59 articles about Ambreinolide 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: 93.0%

ent-8α-hydroxy-labda-13(16),14-dien (10207-79-1) → ambreinolide (468-84-8)

Guidance literature:

ent-8α-hydroxy-labda-13(16),14-dien; With ozone; In methanol; at -78 ℃;

With hydrogen; Lindlar's catalyst; In methanol; at 20 ℃;

DOI:10.1023/A:1012331013282

Reference yield: 92.1%

2-[(1R,2R,4aS,8aS)-2,5,5,8a-Tetramethyl-2-(tetrahydro-pyran-2-yloxy)-decahydro-naphthalen-1-ylmethyl]-malonic acid dimethyl ester (188539-97-1) → ambreinolide (468-84-8)

Guidance literature:

With potassium hydroxide; In ethanol; at 55 ℃; for 1.5h;

DOI:10.1016/S0040-4020(97)00103-8

Reference yield: 92.0%

3-(2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-acrylic acid methyl ester (591215-34-8) → ambreinolide (468-84-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; atmospheric pressure;

DOI:10.1016/j.tetasy.2006.11.015

upstream raw materials:

(5S,9S,10S)-14,15,16-trisnorlabda-8⁽¹⁷⁾-en-13-oic acid

Ambrein

lead(IV) tetraacetate

acetic acid

Downstream raw materials:

8-hydroxy-14,15,16-trinor-8ξH,9ξH-labdan-13-oic acid-lactone

Δ¹¹-ambreinolide

methyl (5S,8R,9R,10S,13S)-8-hydroxylabdan-15-oate

(+)-ambreine

Refernces

• 1、 Kukovinets,Zainullin,Odinokov,Kislitsyn,Roshchin,Galin,Tolstikov. "Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXIV. Synthesis of ambreinolide and 8α,13-Epoxy-14,15,16-trisnorlabd-12-ene proceeding from isoabienol ozonolysis". . p. 235 - 237. Retrieved 2001.
• 2、 Christenson, Philip A.. "Synthesis of Dodecahydro-3a,6,6,69a-tetramethyl naphthofuran via Alkoxy Radical Fragmentation.". . p. 1925 - 1932. Retrieved 1988.
• 3、 Toshima, Hiroaki,Oikawa, Hideaki,Yada, Hiroshi,Ono, Hiroshi,Toyomasu, Tomonobu,Sassa, Takeshi. "Total synthesis of (+/-)-syn-copalol.". . p. 2504 - 2510. Retrieved 2007/10/03.