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Ambroxane
Cas No: 6790-58-5
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[3aR-(3aα,5aβ,9aα,9bβ)]-Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan
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Hot Selling Pure Ambroxide Powder 98% Ambroxan
Cas No: 6790-58-5
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Ambroxane6790-58-5
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Naphtho[2,1-b]furan,dodecahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)- 6790-58-5
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Ambroxane
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6790-58-5 Usage

Definition

ChEBI: A diterpenoid derived from sclareol that is responsible for the odour of ambergris (a solid, waxy, flammable substance produced in the digestive system of sperm whales).
InChI:InChI=1/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3

6790-58-5 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (379220)  (−)-Ambroxide  99% 6790-58-5 379220-5G 1,105.65CNY Detail
Sigma-Aldrich (67369)  (−)-Ambroxide  analytical standard 6790-58-5 67369-100MG 616.59CNY Detail

6790-58-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ambroxan

1.2 Other means of identification

Product number -
Other names (-)-ambrox

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6790-58-5 SDS

6790-58-5Synthetic route

Conditions
ConditionsYield
With RuCl2(2-(diphenylphosphino)-N-(thiophen-2-ylmethyl)ethanamine)PPh3; hydrogen In toluene at 100℃; under 37503.8 Torr; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Autoclave;A 99.5%
B n/a
With RuCl2(2-(diphenylphosphino)-N-(2-(methylthio)ethyl)ethanamine)PPh3; hydrogen; sodium methylate In toluene at 100℃; for 16h; Catalytic behavior; Autoclave;A 67%
B 12%
biscyclohomofarnesane-8α,12-diol
320756-17-0

biscyclohomofarnesane-8α,12-diol

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 11h;98%
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol
38419-75-9

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With n-butyllithium; p-toluenesulfonyl chloride In tetrahydrofuran; hexane at 0 - 20℃;96%
With sodium hydride; p-toluenesulfonyl chloride In dichloromethane at 25℃;94%
With zinc(II) chloride In 1,2-dichloro-ethane for 3h;92%
Δ2(3)-ambrox
1038482-07-3

Δ2(3)-ambrox

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With 10% Pd/C; hydrogen In ethyl acetate at 20℃; for 12h;96%
With palladium 10% on activated carbon; hydrogen In methanol under 760.051 Torr;92%
aqueous sodium sulfate

aqueous sodium sulfate

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol
38419-75-9

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With hydrogenchloride In water; toluene95%
<1R-(1α,2β,4aβ,8aα)>-decahydro-1-(2-chloroethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetate
121067-50-3

<1R-(1α,2β,4aβ,8aα)>-decahydro-1-(2-chloroethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetate

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With potassium hydroxide In water; isopropyl alcohol92%
(3aS,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyl-decahydro-naphtho[2,1-b]furan-4-one
116163-57-6

(3aS,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyl-decahydro-naphtho[2,1-b]furan-4-one

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With potassium hydroxide; hydrazine90%
Conditions
ConditionsYield
With sodium tetrahydroborate; zinc(II) iodide In tetrahydrofuran for 1h; Heating;85%
Multi-step reaction with 2 steps
1: 95 percent / potassium borohydride / ethanol / 10 h / Heating
2: 92 percent / bromotrichloromethane; triphenylphosphine; NaHCO3 / CH2Cl2 / 6 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C
2: 96 percent / n-BuLi; TsCl / hexane; tetrahydrofuran / 0 - 20 °C
View Scheme
<1R-(1α,2β,4aβ,8aα)>-1-decahydro-1-(2-iodoethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetate
121067-46-7

<1R-(1α,2β,4aβ,8aα)>-1-decahydro-1-(2-iodoethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetate

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With potassium hydroxide In water; isopropyl alcohol for 18h; Heating;81%
2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol
31207-73-5

2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol

A

2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol
31222-15-8

2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol

B

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In nitromethane for 18h; Ambient temperature;A n/a
B 80%
2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol
31222-15-8

2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With iron(III) chloride In 1,2-dichloro-ethane at 25℃; Reagent/catalyst; enantioselective reaction;77%
Acidic conditions;
13,14,15,16-tetranor-8βH-labdane-8,12-diol
41747-05-1

13,14,15,16-tetranor-8βH-labdane-8,12-diol

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In nitromethane at 80℃; for 0.5h;76%
With toluene-4-sulfonic acid In nitromethane at 40℃; for 0.0833333h;45%
8α,12-epoxy-13,14,15,16-tetranorlabdan-19-al
152185-80-3

8α,12-epoxy-13,14,15,16-tetranorlabdan-19-al

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate In various solvent(s) for 1h; Heating;71%
With potassium hydroxide; hydrazine hydrate In various solvent(s) for 1h; Heating;71%
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-yl acetate
38419-76-0

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-yl acetate

A

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol
38419-75-9

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

B

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With sodium methylate; carbonic acid dimethyl ester In tetrahydrofuran; methanol at 65℃; for 2h;A 4%
B 67%
<1S-(1α,2β,3β,4β,4aβ,8aα)> decahydro-3-hydroxyl-2,5,5,8a-tetramethylnaphthalene-1-ethanol
158577-90-3

<1S-(1α,2β,3β,4β,4aβ,8aα)> decahydro-3-hydroxyl-2,5,5,8a-tetramethylnaphthalene-1-ethanol

A

(-)-ambroxide
6790-58-5

(-)-ambroxide

B

8β,12-epoxy-13,14,15,16-tetranorlabdane
68365-88-8

8β,12-epoxy-13,14,15,16-tetranorlabdane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 80℃; for 2h;A 48%
B 10%
(1R,2R,4aS,8aS)-1-(3-Hydroperoxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol
105735-95-3, 105735-96-4

(1R,2R,4aS,8aS)-1-(3-Hydroperoxy-3-methyl-pent-4-enyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With copper diacetate; iron(II) sulfate In methanol at 50℃; for 3h;33%
With copper diacetate; iron(II) sulfate In methanol at 50℃; for 3h; Product distribution; other amounts of reagents;
Multi-step reaction with 4 steps
1: triphenylphosphine / diethyl ether / 24 h / 20 °C
2: 83 percent / H2 / 5percent Pd/C / ethanol / 760 Torr / Ambient temperature
3: 1.) aq. NaOCl / 1.) AcOH, CCl4, 0 deg C, 3h, 2.) 30-35 deg C, 3h
4: 80percent NaH / tetrahydrofuran / 3 h / Heating
View Scheme
sclareol
515-03-7

sclareol

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With dihydrogen peroxide In water at 70℃; for 4h;20%
Multi-step reaction with 2 steps
1.1: potassium permanganate; acetic anhydride / acetone / 2 h / 0 °C
1.2: 97 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C
2.1: 92 percent / bromotrichloromethane; triphenylphosphine; NaHCO3 / CH2Cl2 / 6 h / Heating
View Scheme
Multi-step reaction with 6 steps
1.1: peracetic acid; NaOAc / ethyl acetate / 192 h / 20 °C
2.1: 1 N aq. NaOH / 2-methyl-propan-2-ol / 20 °C
2.2: H2SO4 / ethyl acetate / 2 h / 0 - 20 °C
3.1: 97 percent / NaIO4 / tetrahydrofuran; H2O / 16 h / 20 °C
4.1: 95 percent / peracetic acid / 50 - 55 °C
5.1: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C
6.1: 96 percent / n-BuLi; TsCl / hexane; tetrahydrofuran / 0 - 20 °C
View Scheme
C20H39N2O3P
113327-33-6

C20H39N2O3P

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With lithium In various solvent(s) Yield given;
(1R,2R,4aS,8aS)-1-(2-Chloro-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol
113105-33-2

(1R,2R,4aS,8aS)-1-(2-Chloro-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 3h; Heating; Yield given;
Toluene-4-sulfonic acid 2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-ethyl ester

Toluene-4-sulfonic acid 2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-ethyl ester

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
for 1h; Ambient temperature; Yield given;
(4aS,6aR,11aR,11bS)-4,4,6a,11b-Tetramethyl-dodecahydro-7,9-dioxa-cyclohepta[a]naphthalene
38419-77-1

(4aS,6aR,11aR,11bS)-4,4,6a,11b-Tetramethyl-dodecahydro-7,9-dioxa-cyclohepta[a]naphthalene

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane
(4aS)-1t-<2-hydroxy-ethyl>-2t,5,5,8a-tetramethyl-(4ar,8at)-decahydro-<2c>naphthol

(4aS)-1t-<2-hydroxy-ethyl>-2t,5,5,8a-tetramethyl-(4ar,8at)-decahydro-<2c>naphthol

(-)-ambroxide
6790-58-5

(-)-ambroxide

(4aS)-1t(?)-<2-hydroxy-ethyl>-2c(?),5,5,8a-tetramethyl-(4ar,8at-decahydro-<2t?>naphthol

(4aS)-1t(?)-<2-hydroxy-ethyl>-2c(?),5,5,8a-tetramethyl-(4ar,8at-decahydro-<2t?>naphthol

A

(-)-ambroxide
6790-58-5

(-)-ambroxide

B

8β,12-epoxy-13,14,15,16-tetranorlabdane
68365-88-8

8β,12-epoxy-13,14,15,16-tetranorlabdane

Conditions
ConditionsYield
With naphthalene-2-sulfonate Erhitzen unter vermindertem Druck;
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol
38419-75-9

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

A

2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol
31207-73-5

2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6, 7,8,8a-octahydronaphthalen-1-yl)ethan-1-ol

B

2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol
31222-15-8

2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol

C

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane for 0.5h; Heating; Title compound not separated from byproducts;A 7.2 % Chromat.
B 16.8 % Chromat.
C 67.4 % Chromat.
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 1h; Title compound not separated from byproducts;A 7.6 % Chromat.
B 16.8 % Chromat.
C 65.2 % Chromat.
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol
38419-75-9

(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

A

2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol
31222-15-8

2-[(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1-yl]ethanol

B

(-)-ambroxide
6790-58-5

(-)-ambroxide

C

8β,12-epoxy-13,14,15,16-tetranorlabdane
68365-88-8

8β,12-epoxy-13,14,15,16-tetranorlabdane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane for 30h; Heating; Title compound not separated from byproducts;A 11.2 % Chromat.
B 29.6 % Chromat.
C 59.1 % Chromat.
(E,E)-homofarnesyl triethylsilyl ether
425681-11-4

(E,E)-homofarnesyl triethylsilyl ether

A

(+)-ambrox (ent-1)

(+)-ambrox (ent-1)

B

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
Stage #1: (E,E)-homofarnesyl triethylsilyl ether With (R)-2-(o-fluorobenzyloxy)-2'-methoxy-1,1'-binaphthyl*SnCl4 In toluene at -78℃; for 72h;
Stage #2: With 1H-imidazole; triethylsilyl chloride In N,N-dimethyl-formamide at 20℃; for 5h;
Stage #3: With TFA*SnCl4 In toluene at -78℃; for 24h; Further stages. Title compound not separated from byproducts.;
(4aS)-1t(?)-<2-hydroxy-ethyl>-2c(?),5,5,8a-tetramethyl-(4ar,8at)-decahydro-<2t?>naphthol

(4aS)-1t(?)-<2-hydroxy-ethyl>-2c(?),5,5,8a-tetramethyl-(4ar,8at)-decahydro-<2t?>naphthol

A

(-)-ambroxide
6790-58-5

(-)-ambroxide

B

8β,12-epoxy-13,14,15,16-tetranorlabdane
68365-88-8

8β,12-epoxy-13,14,15,16-tetranorlabdane

Conditions
ConditionsYield
With naphthalene-2-sulfonate Erhitzen unter vermindertem Druck;
8-hydroxy-15,16-dinor-labdan-13-one
16736-51-9

8-hydroxy-15,16-dinor-labdan-13-one

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 83 percent / sodium chromate; acetic anhydride; glacial acetic acid / benzene / 4 h / 70 °C
2: 95 percent / potassium borohydride / ethanol / 10 h / Heating
3: 92 percent / bromotrichloromethane; triphenylphosphine; NaHCO3 / CH2Cl2 / 6 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 83 percent / sodium chromate; acetic anhydride; glacial acetic acid / benzene / 4 h / 70 °C
2: 85 percent / zinc iodide; sodium borohydride / tetrahydrofuran / 1 h / Heating
View Scheme
Farnesal
502-67-0

Farnesal

(-)-ambroxide
6790-58-5

(-)-ambroxide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 96 percent / PhLi / tetrahydrofuran; cyclohexane; diethyl ether / 1 h / 20 °C
2.1: tetrahydrofuran / 24 h / 20 °C
3.1: H2O2; NaOH / tetrahydrofuran
4.1: 100 percent / imidazole / dimethylformamide / 20 °C
5.1: (R)-2-(o-fluorobenzyloxy)-2'-methoxy-1,1'-binaphthyl*SnCl4 / toluene / 72 h / -78 °C
5.2: ClSiEt3; imidazole / dimethylformamide / 5 h / 20 °C
5.3: TFA*SnCl4 / various solvent(s); toluene / 24 h / -78 °C
View Scheme
2-((trifluoromethyl)thio)isoindoline-1,3-dione
719-98-2

2-((trifluoromethyl)thio)isoindoline-1,3-dione

(-)-ambroxide
6790-58-5

(-)-ambroxide

(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2-((trifluoromethyl)thio)dodecahydronaphtho[2,1-b]furan

(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2-((trifluoromethyl)thio)dodecahydronaphtho[2,1-b]furan

Conditions
ConditionsYield
With sodium benzoate; [Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(4,4'-di-tert-butyl-2,2'-bipyridine)](PF6) In acetonitrile at 20℃; for 2h; Inert atmosphere; Irradiation; regioselective reaction;95%
Conditions
ConditionsYield
With dipotassium hydrogenphosphate; C17H18ClFeN6O6(2-); 3-chloro-benzenecarboperoxoic acid In water; acetonitrile at 20℃;90%
With (R,R)-Fe(PDP); dihydrogen peroxide; acetic acid regioselective reaction;80%
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetramesitylporphyrinato)ruthenium(IV) In 1,2-dichloro-ethane at 40℃; for 24h; Reagent/catalyst; Inert atmosphere; regioselective reaction;80%
P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

(-)-ambroxide
6790-58-5

(-)-ambroxide

ambroxide-12-carbonitrile
1338695-87-6

ambroxide-12-carbonitrile

Conditions
ConditionsYield
With benzophenone In acetonitrile at 20℃; for 2h; Inert atmosphere; UV-irradiation; stereoselective reaction;89%
With benzophenone In acetonitrile at 20℃; for 2h; Inert atmosphere; UV-irradiation; chemoselective reaction;89%
1,1-bis(phenylsulfonyl)ethylene
39082-53-6

1,1-bis(phenylsulfonyl)ethylene

(-)-ambroxide
6790-58-5

(-)-ambroxide

C30H40O5S2

C30H40O5S2

Conditions
ConditionsYield
With [Ir(dF(CF3)ppy)2(5,5'dCF3bpy)]PF6; dibutylphosphoric acid tetrabutylammonium salt In dichloromethane at 20℃; for 24h; Glovebox; Inert atmosphere; Irradiation;88%
With 2-chloroanthracene-9,10-dione In dichloromethane at 20℃; for 4h; Irradiation; Optical yield = 48 %de; diastereoselective reaction;
(-)-ambroxide
6790-58-5

(-)-ambroxide

C16H27N3O

C16H27N3O

Conditions
ConditionsYield
With 4-toluenesulfonyl azide; 4-Benzoylpyridine In benzene at 20℃; for 3h; UV-irradiation; Inert atmosphere; chemoselective reaction;77%
(prop-2-ene-1,2-diyldisulfonyl)dibenzene
2525-55-5

(prop-2-ene-1,2-diyldisulfonyl)dibenzene

(-)-ambroxide
6790-58-5

(-)-ambroxide

C25H36O3S

C25H36O3S

Conditions
ConditionsYield
With pentacene-5,7,12,14-tetraone; potassium carbonate In dichloromethane at 20℃; for 24h; Inert atmosphere; Irradiation;74%
(-)-ambroxide
6790-58-5

(-)-ambroxide

(1S,6S)-2-(2-bromoethyl)-1,3,7,7-tetramethylbicyclo[4.4.0]dec-2-ene
308255-94-9

(1S,6S)-2-(2-bromoethyl)-1,3,7,7-tetramethylbicyclo[4.4.0]dec-2-ene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; tetraethylammonium bromide In dichloromethane at 20℃; Ring cleavage;72%
(4-methoxy)benzenesulfonylmethanal O-benzyl oxime

(4-methoxy)benzenesulfonylmethanal O-benzyl oxime

(-)-ambroxide
6790-58-5

(-)-ambroxide

C24H35NO2

C24H35NO2

Conditions
ConditionsYield
With 4-Benzoylpyridine In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; UV-irradiation;70%
(-)-ambroxide
6790-58-5

(-)-ambroxide

(4aS,8aS)-5-(2-iodoethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene
308255-96-1

(4aS,8aS)-5-(2-iodoethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene

Conditions
ConditionsYield
With aluminium trichloride; sodium iodide In dichloromethane; acetonitrile at 20℃; Ring cleavage;69%
4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

(-)-ambroxide
6790-58-5

(-)-ambroxide

A

methyl 4-((2R,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)benzoate

methyl 4-((2R,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)benzoate

B

methyl 4-((2S,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)benzoate

methyl 4-((2S,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)benzoate

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); 5,5'-dimethyl-2,2'-bipyridine; (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; sodium carbonate In benzene at 20℃; for 96h; Schlenk technique; diastereoselective reaction;A 69%
B n/a
With bis(acetylacetonate)nickel(II); 5,5'-dimethyl-2,2'-bipyridine; (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; sodium hydrogencarbonate In benzene at 20℃; for 96h; Schlenk technique; Inert atmosphere; Irradiation; Overall yield = 69 %; Overall yield = 76.7 mg; diastereoselective reaction;A n/a
B n/a
Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

(-)-ambroxide
6790-58-5

(-)-ambroxide

2-(phenyl((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)methyl)malononitrile

2-(phenyl((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)methyl)malononitrile

Conditions
ConditionsYield
With eosin In tert-butyl alcohol at 0 - 60℃; for 48h; Sealed tube; Inert atmosphere; Irradiation;68%
(-)-ambroxide
6790-58-5

(-)-ambroxide

C16H28O3
1217488-90-8

C16H28O3

Conditions
ConditionsYield
With Botrytis cynerea for 72h; Microbiological reaction; chemoselective reaction;60%
Conditions
ConditionsYield
With [((S,S)-N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine)FeII(OTf)2]; dihydrogen peroxide; acetic acid In water; acetonitrile at 0 - 20℃; Catalytic behavior; Inert atmosphere; regiospecific reaction;A 29%
B 54%
isoquinoline
119-65-3

isoquinoline

(-)-ambroxide
6790-58-5

(-)-ambroxide

1-((3aR,5aS,9aS,9bR)-3 a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)isoquinoline

1-((3aR,5aS,9aS,9bR)-3 a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)isoquinoline

Conditions
ConditionsYield
With ethanol; bis-[(trifluoroacetoxy)iodo]benzene In dimethyl sulfoxide; 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; diastereoselective reaction;53%

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