(+/-)-lindestrene

Base Information

• Chemical Name: (+/-)-lindestrene
• CAS No.: 16836-53-6
• Molecular Formula: C₁₅H₁₈O
• Molecular Weight: 214.307
• Mol file: 16836-53-6.mol

Synonyms:

Chemical Property of (+/-)-lindestrene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-lindestrene

There total 11 articles about (+/-)-lindestrene 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:

(4'aS,8'aS)-8'a-Methyl-5'-methylene-3',4',4'a,5',6',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene] → (+/-)-lindestrene (2221-88-7,4857-12-9,16836-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1N HCl / tetrahydrofuran / 0.5 h / 60 °C

2: 1.) LDA, ZnCl₂ / 2.) p-TsOH / 1.) -78 deg C to -0 deg C, 2.) THF, H₂O, 60 deg C, 0.5 h

With hydrogenchloride; zinc(II) chloride; lithium diisopropyl amide; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)84607-4

Reference yield:

((4'aS,5'R,8'aS)-8'a-Methyl-3',4',4'a,5',6',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-yl)-methanol (105631-45-6) → (+/-)-lindestrene (2221-88-7,4857-12-9,16836-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) o-C₆H₄(NO₂)SeCN, n-Bu₃P, 2.) 30percent H₂O₂ / 1.) THF, room temp., 0.5 h, 2.) THF, room temp., 16 h

2: 1N HCl / tetrahydrofuran / 0.5 h / 60 °C

3: 1.) LDA, ZnCl₂ / 2.) p-TsOH / 1.) -78 deg C to -0 deg C, 2.) THF, H₂O, 60 deg C, 0.5 h

With hydrogenchloride; ortho-nitrophenyl selenocyanate; tributylphosphine; dihydrogen peroxide; zinc(II) chloride; lithium diisopropyl amide; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)84607-4

Reference yield:

6-Methoxy-4a-methyl-4-oxo-1,2,3,4,4a,7-hexahydro-naphthalene-1-carboxylic acid → (+/-)-lindestrene (2221-88-7,4857-12-9,16836-53-6)

Guidance literature:

Multi-step reaction with 11 steps

1: diethyl ether / 0.5 h / -10 °C

2: NaBH₄ / ethanol / 0.5 h / 0 °C

3: 0.5M (CO₂H)2 / 0.5 h / Ambient temperature

4: 57 percent / H₂ / Pd-C / ethanol / Ambient temperature

5: 81 percent / p-TsOH / benzene / Heating

6: 1.) NaH / 1.) THF, 3 h, room temp., 2.) 40 h, room temp.

7: 80 percent / biphenyl / 16 h / 210 °C

8: 79 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

9: 1.) o-C₆H₄(NO₂)SeCN, n-Bu₃P, 2.) 30percent H₂O₂ / 1.) THF, room temp., 0.5 h, 2.) THF, room temp., 16 h

10: 1N HCl / tetrahydrofuran / 0.5 h / 60 °C

11: 1.) LDA, ZnCl₂ / 2.) p-TsOH / 1.) -78 deg C to -0 deg C, 2.) THF, H₂O, 60 deg C, 0.5 h

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; tributylphosphine; hydrogen; dihydrogen peroxide; oxalic acid; sodium hydride; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; biphenyl; diethyl ether; ethanol; benzene;

DOI:10.1016/S0040-4039(01)84607-4

upstream raw materials:

1-hydroxypropan-2-one tetrahydropyran ether

(4aS,8aS)-8a-Methyl-5-methylene-3,4,4a,5,6,8a-hexahydro-1H-naphthalen-2-one

((4'aS,5'R,8'aS)-8'a-Methyl-3',4',4'a,5',6',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-yl)-methanol

(1S,4S,4aS)-4-Hydroxy-4a-methyl-6-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalene-1-carboxylic acid methyl ester