5-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2β,3α-dimethylnaphthalen-1-yl]-1,3-benzodioxole

Base Information

• Chemical Name: 5-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2β,3α-dimethylnaphthalen-1-yl]-1,3-benzodioxole
• CAS No.: 24150-38-7
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.419
• Mol file: 24150-38-7.mol

Synonyms:1,3-Benzodioxole,5-(1,2,3,4-tetrahydro-6,7-dimethoxy-2,3-dimethyl-1-naphthalenyl)-, [1S-(1a,2b,3a)]-; Naphthalene, 1,2,3,4-tetrahydro-6,7-dimethoxy-2b,3a-dimethyl-1a-[3,4-(methylenedioxy)phenyl]- (7CI,8CI);(+)-Isogalcatin; Isogalcatin; Isootobain; O-Methylotobaphenol; Otobaphenol,O-methyl-

Chemical Property of 5-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2β,3α-dimethylnaphthalen-1-yl]-1,3-benzodioxole

Chemical Property:

• PSA: 36.92000
• LogP: 4.39270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2β,3α-dimethylnaphthalen-1-yl]-1,3-benzodioxole

There total 21 articles about 5-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2β,3α-dimethylnaphthalen-1-yl]-1,3-benzodioxole 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: 80.0%

C21H26O5 → (-)-Isogalcatin (10240-19-4,24150-38-7,96170-95-5)

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile; at 20 ℃;

DOI:10.1016/j.bmcl.2018.04.049

Reference yield:

(E)-3-(methoxycarbonyl)-4-(3,4-dimethoxyphe-nyl)but-3-enoic acid (115061-18-2) → isogalcatin (10240-19-4,24150-38-7,96170-95-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 10 g / hydrogen / 10percent palladium-charcoal / methanol / 5 h

2: 11.2 g / potassium hydroxide / ethanol; H₂O

3: 6.4 g / calcium chloride, sodium borohydride / ethanol / 1.) -10 deg C, 3 h, 2.) room temperature, 5 h

4: 1.) lithium di-isopropylamide, 2.) trifluoroacetic acid / 1.) THF, -20 deg C, 1 h, 2.) dichloromethane, room temperature, 3 h

5: 1.15 g / lithium aluminium hydride / tetrahydrofuran / 3 h / Ambient temperature

6: 1.) toluene-p-sulphonyl chloride, pyridine, 2.) lithium aluminium hydride / 1.) 0 deg C, 2 h, 2.) THF

With pyridine; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; p-toluenesulfonyl chloride; trifluoroacetic acid; calcium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1039/P19810001681

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → isogalcatin (10240-19-4,24150-38-7,96170-95-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 13.5 g / sodium methoxide / methanol / 1.5 h / Heating

2: 10 g / hydrogen / 10percent palladium-charcoal / methanol / 5 h

3: 11.2 g / potassium hydroxide / ethanol; H₂O

4: 6.4 g / calcium chloride, sodium borohydride / ethanol / 1.) -10 deg C, 3 h, 2.) room temperature, 5 h

5: 1.) lithium di-isopropylamide, 2.) trifluoroacetic acid / 1.) THF, -20 deg C, 1 h, 2.) dichloromethane, room temperature, 3 h

6: 1.15 g / lithium aluminium hydride / tetrahydrofuran / 3 h / Ambient temperature

7: 1.) toluene-p-sulphonyl chloride, pyridine, 2.) lithium aluminium hydride / 1.) 0 deg C, 2 h, 2.) THF

With pyridine; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; sodium methylate; p-toluenesulfonyl chloride; trifluoroacetic acid; calcium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1039/P19810001681

upstream raw materials:

1,2-(methylenedioxy)-4-bromobenzene

t-2,c-3-bishydroxymethyl-6,7-dimethoxy-r-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydronaphthalene

dimethyl sulfate

(6S,7R,8R)-8-Benzo[1,3]dioxol-5-yl-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol

Refernces

• 1、 Liu, Xiaoyu,Chen, Panpan,Li, Xiaoyu,Ba, Mingyu,Jiao, Xiaozhen,Guo, Ying,Xie, Ping. "Design, synthesis and biological evaluation of substituted (+)-SG-1 derivatives as novel anti-HIV agents". . p. 1699 - 1703. Retrieved 2018/05/04.
• 2、 Mpango, G. B.,Snieckus, V.. "TANDEM CONJUGATE ADDITION-α-ALKYLATION OF UNSATURATED AMIDES. SYNTHESIS OF 1-ARYLTETRALIN LIGNANS". . p. 4827 - 4830. Retrieved 2007/10/02.