decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one

Base Information

• Chemical Name: decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one
• CAS No.: 1216-84-8
• Molecular Formula: C16H26 O2
• Molecular Weight: 250.381
• European Community (EC) Number: 214-933-8
• DSSTox Substance ID: DTXSID50859489
• Nikkaji Number: J217.066C
• Wikidata: Q7434120
• Metabolomics Workbench ID: 46913
• Mol file: 1216-84-8.mol

Synonyms:1-Naphthaleneaceticacid, decahydro-2-hydroxy-2,5,5,8a-tetramethyl-, g-lactone (6CI,7CI,8CI); 3a,6,6,9a-Tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one

Chemical Property of decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one

Chemical Property:

• Vapor Pressure: 0.000299mmHg at 25°C
• Boiling Point: 321.4°Cat760mmHg
• Flash Point: 132.4°C
• Density: 1.009g/cm³
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 250.193280068
• Heavy Atom Count: 18
• Complexity: 387

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(C2CC(=O)O3)C)C)C

Technology Process of decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one

There total 171 articles about decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one 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: 99.0%

2-((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)propan-2-ol (145511-21-3) → (3aR)-(+)-sclareolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5)

Guidance literature:

With sodium chromate(VI); sodium acetate; acetic anhydride; acetic acid; In benzene; at 40 ℃; for 5h;

DOI:10.1016/S0040-4020(01)92289-6

Reference yield: 97.0%

12(R,S)-15-Acetoxy-8,12 epoxylabdane → (3aR)-(+)-sclareolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5)

Guidance literature:

With sodium chromate(VI); sodium acetate; acetic anhydride; In acetic acid; at 30 - 40 ℃; for 12h;

DOI:10.1016/S0040-4020(01)88343-5

Reference yield: 95.0%

8α,13(S)-epoxy-15-nor-labdan-14-al (52104-92-4) → (3aR)-(+)-sclareolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5)

Guidance literature:

With peracetic acid; at 50 - 55 ℃;

DOI:10.1081/SCC-100103265

upstream raw materials:

sclareol

((1R,2R,8aS)-2-Acetoxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-acetic acid methyl ester

((1R,2R,8aS)-2-Acetoxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-acetic acid

N,N-dimethylhomofarnesic acid amide

Downstream raw materials:

2-Hydroxy-2,5,5,8a-tetramethyl-1-(2-hydroxyethyl)-decahydronaphthalene

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

C₂₀H₃₀O₃

5S,9S,10S-(-)-(E)-labda-8⁽¹⁷⁾,11,13-trien-16,15-olide

Refernces

• 1、 Murai, Akio,Abiko, Atsushi,Masamune, Tadashi. "TOTAL SYNTHESIS OF (+/-)-APLYSIN-20". . p. 4955 - 4958. Retrieved 1984.
• 2、 Ma, Miaofeng,Feng, Jili,Li, Ruoxin,Chen, Shu-Wei,Xu, Hui. "Synthesis and antifungal activity of ethers, alcohols, and iodohydrin derivatives of sclareol against phytopathogenic fungi in vitro". . p. 2773 - 2777. Retrieved 2015.
• 3、 Lederer et al.. "-". . p. 789,792. Retrieved 1951.
• 4、 Teresa, J. de Pascual,Urones, J. G.,Pedrero, A. Montanna,Barcala, P. Basabe. "FUNCTIONALIZATION AT C-12 IN LABDANIC DITERPENES: SYNTHESIS OF THE NATURAL DITERPENIC LACTONES ISOLATED FROM CISTUS LADANIFERUS L.". . p. 5717 - 5720. Retrieved 1985.
• 5、 Seitz, Miriam,Syrén, Per-Olof,Steiner, Lisa,Klebensberger, Janosch,Nestl, Bettina M.,Hauer, Bernhard. "Synthesis of Heterocyclic Terpenoids by Promiscuous Squalene-Hopene Cyclases". . p. 436 - 439. Retrieved 2013.
• 6、 Ruzicka,Janot. "-". . p. 645,648. Retrieved 1931.
• 7、 Hodges,Reed. "-". . p. 71,74. Retrieved 1960.
• 8、 Moulines,Lamidey,Desvergnes-Breuil. "A practical synthesis of ambrox from sclareol using no metallic oxidant". . p. 749 - 758. Retrieved 2001.
• 9、 Schelwies, Mathias,Paciello, Rocco,Pelzer, Ralf,Siegel, Wolfgang,Breuer, Michael. "Palladium-Catalyzed Low Pressure Carbonylation of Allylic Alcohols by Catalytic Anhydride Activation". . p. 9263 - 9266. Retrieved 2021/05/27.
• 10、 -. "METHOD FOR PRODUCING SCLAREOLIDE". Paragraph 0027; 0028. . Retrieved 2020/12/30.