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101692-02-8

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Basic Information
CAS No.: 101692-02-8
Name: (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]indene-2,5-diol
Article Data: 11
Molecular Structure:
Molecular Structure of 101692-02-8 ((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]indene-2,5-diol)
Formula: N/A
Molecular Weight: 332.483
Synonyms: (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol
Density: 1.106±0.06 g/cm3(Predicted)
Melting Point: 113-115 °C
Boiling Point: 506.1±50.0 °C(Predicted)
Related products
Synthetic route
101692-01-7

(1R,2R,3aS,9aS)-1-[(3S)-3-hydroxyoctyl]-5-methoxy-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-2-ol

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
With aluminum (III) chloride; 1-dodecylthiol In dichloromethane at 0 - 20℃; Inert atmosphere;95%
With n-butyllithium; diphenylphosphane In tetrahydrofuran; hexane for 20h; Heating;80%
With n-butyllithium; diphenylphosphane In tetrahydrofuran; hexane for 19h; Reflux;8.3 g
1425937-56-9

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 1h;85%
With methanol; sodium hydroxide at 20℃; for 1h;85%
1613271-23-0

(1R,2R,3aS,9aS)-2-((tert-butyldiphenylsilyl)oxy)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-ol

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20 - 50℃; for 25.5h; Reagent/catalyst; Temperature; Inert atmosphere;77%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20 - 50℃; for 25.5h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;77%
1425937-55-8

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S,1E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 28h;73%
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 28h;73%
Multi-step reaction with 2 steps
1: hydrogen; 5%-palladium/activated carbon / methanol / 5 h / 20 °C
2: sodium hydroxide / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; 5%-palladium/activated carbon / methanol / 5 h / 20 °C
2: sodium hydroxide; methanol / 1 h / 20 °C
View Scheme
1257983-83-7

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((3S,1E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalene-2,5-diol

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; potassium hydroxide In methanol at 20℃;72%
With 5%-palladium/activated carbon; hydrogen; potassium hydroxide In methanol at 20℃;72%

C21H29ClO3

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; triethylamine In methanol for 15h;65%
6971-51-3

3-methoxybenzyl alcohol

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 94 percent / imidazole / CH2Cl2
2: n-BuLi / hexane / 24 h / 0 - 20 °C
3: 4695 g / TBAF / tetrahydrofuran / 20 °C
4: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
5: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C
6: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C
7: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C
8: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C
9: CH2Cl2 / 2 h / 20 °C
10: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr
11: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C
12: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C
13: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating
View Scheme
136911-16-5

(2-allyl-3-methoxyphenyl)methanol

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
2: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C
3: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C
4: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C
5: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C
6: CH2Cl2 / 2 h / 20 °C
7: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr
8: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C
9: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C
10: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating
View Scheme
153974-48-2

3-methoxy-O-tert-butyldimethylsilylbenzyl alcohol

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: n-BuLi / hexane / 24 h / 0 - 20 °C
2: 4695 g / TBAF / tetrahydrofuran / 20 °C
3: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
4: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C
5: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C
6: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C
7: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C
8: CH2Cl2 / 2 h / 20 °C
9: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr
10: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C
11: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C
12: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating
View Scheme
81007-64-9

(S)-1-chloroheptane-2-ol

101692-02-8

(1R,2R,3aS,9aS)-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: TsOH*pyridine / CH2Cl2 / 15 h / 20 °C
2: BuLi / tetrahydrofuran; hexane / 15 h / 0 - 20 °C
3: NaOH / ethanol / 20 h / 20 °C
4: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C
5: 75 percent / PCC / CH2Cl2 / 15 h / 0 - 20 °C
6: BH3; Me2S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C
7: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 15 h / 20 °C
8: CH2Cl2 / 2 h / 20 °C
9: H2; K2CO3 / Pd/C / ethanol / 20 °C / 4654.33 Torr
10: NaBH4; aq. NaOH / ethanol / 6 h / -10 °C
11: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C
12: 80 percent / Ph2PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating
View Scheme
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