Naphtho(1,2-c)furan-1(3H)-one, 4,5,5a,6,7,8,9,9a-octahydro-6,6,9a-trimethyl-, trans-

Base Information

• Chemical Name: Naphtho(1,2-c)furan-1(3H)-one, 4,5,5a,6,7,8,9,9a-octahydro-6,6,9a-trimethyl-, trans-
• CAS No.: 1684-54-4
• Molecular Formula: C15H22 O2
• Molecular Weight: 234.338
• DSSTox Substance ID: DTXSID30168561
• Nikkaji Number: J14.530K
• Wikidata: Q83038175
• Mol file: 1684-54-4.mol

Synonyms:Isodrimenin;(+)-Isodrimenin;1684-54-4;4,5,5a,6,7,8,9,9a-Octahydro-6,6,9a-trimethylnaphtho(1,2-c)furan-1(3H)-one trans-;Naphtho(1,2-c)furan-1(3H)-one, 4,5,5a,6,7,8,9,9a-octahydro-6,6,9a-trimethyl-, trans-;MEGPFBRAROUGQD-NHYWBVRUSA-;DTXSID30168561;InChI=1/C15H22O2/c1-14(2)7-4-8-15(3)11(14)6-5-10-9-17-13(16)12(10)15/h11H,4-9H2,1-3H3/t11-,15-/m0/s1

Chemical Property of Naphtho(1,2-c)furan-1(3H)-one, 4,5,5a,6,7,8,9,9a-octahydro-6,6,9a-trimethyl-, trans-

Chemical Property:

• Vapor Pressure: 1.57E-05mmHg at 25°C
• Boiling Point: 365.5°C at 760 mmHg
• Flash Point: 152.9°C
• Density: 1.07g/cm³
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 405

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3=C2C(=O)OC3)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CCC3=C2C(=O)OC3)(C)C

Technology Process of Naphtho(1,2-c)furan-1(3H)-one, 4,5,5a,6,7,8,9,9a-octahydro-6,6,9a-trimethyl-, trans-

There total 8 articles about Naphtho(1,2-c)furan-1(3H)-one, 4,5,5a,6,7,8,9,9a-octahydro-6,6,9a-trimethyl-, trans- 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: 75.0%

(5aS,9aS)-1,3-Dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan (81306-20-9,81369-47-3,81369-48-4,81369-51-9,87859-71-0) → (+)-isodrimenin (1684-54-4) + (+)-confertifoline (1811-23-0)

Guidance literature:

With hydrogenchloride; In diethyl ether; acetone; for 0.5h; Ambient temperature;

Reference yield: 10.0%

(5aR,9aR)-1,3-Dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan (81306-20-9,81369-47-3,81369-48-4,81369-51-9,87859-71-0) → (+/-)-confertifolin (1811-23-0,69779-99-3,123809-45-0) + (+/-)-isodrimenin (1684-54-4)

Guidance literature:

With hydrogenchloride; In acetone; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(01)83030-6

Reference yield:

11,12-diethoxy-11,12-epoxydrim-8-ene (124313-88-8,124377-32-8,124377-33-9,124377-34-0) → (+)-isodrimenin (1684-54-4) + (+)-confertifoline (1811-23-0)

Guidance literature:

With hydrogenchloride; In acetone; for 0.5h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/0040-4020(89)80155-3

upstream raw materials:

(5aS,9aS)-1,3-Dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan

(+)-winterin

11,12-diethoxy-11,12-epoxydrim-8-ene

(5aR,9aR)-1,3-Dimethoxy-6,6,9a-trimethyl-1,3,4,5,5a,6,7,8,9,9a-decahydro-naphtho[1,2-c]furan

Downstream raw materials:

7α-hydroxy-8-drimen-11,12-olide

Refernces

• 1、 Hueso-Rodriguez, Juan A.,Rodriguez, Benjamin. "A NEW AND EFFICIENT ROUTE TO OPTICALLY ACTIVE DRIMANES. SYNTHESIS OF (+)-WINTERIN, (+)-CONFERTIFOLIN, (+)-ISODRIMENIN, AND (+)-BICYCLOFARNESOL". . p. 1567 - 1576. Retrieved 2007/10/02.
• 2、 Ley, Steven V.,Mahon, Michael. "Synthesis of the Drimane-related Sesquiterpenes Euryfuran, Confertifolin, and Valdiviolide". . p. 1379 - 1381. Retrieved 2007/10/02.