(1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one

Base Information

• Chemical Name: (1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one
• CAS No.: 1379474-00-6
• Molecular Formula: C₂₄H₂₈Cl₂O₄
• Molecular Weight: 451.39
• Mol file: 1379474-00-6.mol

Synonyms:(1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one

Chemical Property of (1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one

There total 4 articles about (1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-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: 63.0%

(1S,3'aR,4'aR,8'aR,9'aR)-2,2-dichloro-8'a-methyl-3'-methylenedecahydro-2'H-spiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one (1379473-95-6) + 1-iodo-3,4-dimethoxybenzene (5460-32-2) → (1S,3'aR,4'aR,8'aR,9'aR,E)-2,2-dichloro-3'-(3,4-dimethoxybenzylidene)-8'a-methyldecahydro-2'H-spiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one (1379473-99-0) + (1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one (1379474-00-6)

Guidance literature:

With palladium diacetate; caesium carbonate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 120 ℃; for 8h; Inert atmosphere; Molecular sieve;

DOI:10.1007/s10600-012-0213-5

Reference yield:

isoalantolactone (470-17-7) → (1S,3'aR,4'aR,8'aR,9'aR,E)-2,2-dichloro-3'-(3,4-dimethoxybenzylidene)-8'a-methyldecahydro-2'H-spiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one (1379473-99-0) + (1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one (1379474-00-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 1.9 h / -5 °C

2: palladium diacetate; caesium carbonate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere; Molecular sieve

With N-benzyl-N,N,N-triethylammonium chloride; palladium diacetate; caesium carbonate; tris-(o-tolyl)phosphine; sodium hydroxide; In water; N,N-dimethyl-formamide; 2: Heck reaction;

DOI:10.1007/s10600-012-0213-5

Reference yield:

C20H29Cl2NO3 → (1S,3'aR,4'aR,8'aR,9'aR,E)-2,2-dichloro-3'-(3,4-dimethoxybenzylidene)-8'a-methyldecahydro-2'H-spiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one (1379473-99-0) + (1S,4'aR,8'aR,9'aS)-2,2-dichloro-3'-(3,4-dimethoxybenzyl)-8'a-methyl-4',4'a,6',7',8',8'a,9',9'a-octahydro-2'Hspiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one (1379474-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile / 2 h / 20 °C

2: sodium hydrogencarbonate / water

3: palladium diacetate; caesium carbonate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere; Molecular sieve

With palladium diacetate; sodium hydrogencarbonate; caesium carbonate; tris-(o-tolyl)phosphine; In water; N,N-dimethyl-formamide; acetonitrile; 3: Heck reaction;

DOI:10.1007/s10600-012-0213-5

upstream raw materials:

isoalantolactone

(1S,3'aR,4'aR,8'aR,9'aR)-2,2-dichloro-8'a-methyl-3'-methylenedecahydro-2'H-spiro{cyclopropan-1,5'-naphtho[2,3-b]furan}-2'-one

1-iodo-3,4-dimethoxybenzene