Ambrox Dl
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Product Name :
Ambrox Dl
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CAS No :
3738-00-9
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Project State :
Commercial
Application
General Description
Cost-effective and customizable Ambrox Dl 3738-00-9 supplier
- Molecular Formula:C16H28 O
- Molecular Weight:236.398
- Appearance/Colour:White crystalline solid
- Melting Point:75-85ºC
- Boiling Point:273.9 ºC at 760 mmHg
- Flash Point:104.8 ºC
- PSA：9.23000
- Density:0.939 g/cm3
- LogP:4.40800
AMBROX DL(Cas 3738-00-9) Usage
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Preparation |
Racemic sclareolide can be prepared by cyclization of homofarnesic acid in the presence of SnCl4 as a catalyst . Pure diastereomers are obtained by acid cyclization of (E)- and (Z)-4-methyl-6-(2,6,6-trimethylcyclohex-l(2)-enyl)-3- hexen-1-ol, prepared from 2-methyl-4-(2,6,6-trimethylcyclohex-l(2)-enyl)-2- butenal [394]. If the racemic sclareolide mixture is resolved into its enantiomers, the (–)-oxide may also be obtained by a totally synthetic route |
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Synthesis Reference(s) |
Synthesis, p. 216, 1983 DOI: 10.1055/s-1983-30287 |
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Trade name |
Compound starting from natural sclareol: Ambermore, Ambermore-DL, Ambermore-EX (Aromor), Ambrox? Super (Firmenich), Ambroxan? (Kao), Ambroxide (Symrise); compound starting from homofarnesic acid derivatives: Ambrox? DL (Firmenich); compound starting from 2-methyl- 4-(2,6,6-trimethylcyclohex-l(2)enyl)-2-butenal: Cetalox? (Firmenich), Cetalor (Aromor). |
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
3738-00-9 Relevant articles
Synthesis and Applications of Cyclohexenyl Halides Obtained by a Cationic Carbocyclisation Reaction
Alonso, Pedro,Pardo, Pilar,Fontaneda, Raquel,Fa?anás, Francisco J.,Rodríguez, Félix
, p. 13158 - 13163 (2017/09/06)
The synthesis of cyclic alkenyl halides ...
Diastereoselective Synthesis of (±)-Ambrox by Titanium(III)-Catalyzed Radical Tandem Cyclization
Rosales, Antonio,Foley,Padial, Natalia M.,Muoz-Bascn, Juan,Sancho-Sanz, Iris,Roldan-Molina, Esther,Pozo-Morales, Laura,Iras-lvarez, Adriana,Rodrguez-Maecker, Roman,Rodrguez-Garca, Ignacio,Oltra, J. Enrique
, p. 369 - 374 (2016/02/09)
A synthesis of (±)-ambrox, a compound wi...
Scalable Synthesis of the Amber Odorant 9-epi-Ambrox through a Biomimetic Cationic Cyclization/Nucleophilic Bromination Reaction
Fontaneda, Raquel,Alonso, Pedro,Fa?anás, Francisco J.,Rodríguez, Félix
supporting information, p. 4626 - 4629 (2016/09/28)
A novel biomimetic nucleophilic bromocyc...
Synthesis of five-membered cyclic ethers by reaction of 1,4-diols with dimethyl carbonate
Aricó, Fabio,Tundo, Pietro,Maranzana, Andrea,Tonachini, Glauco
experimental part, p. 1578 - 1586 (2012/10/07)
The reaction of 1,4-diols with dimethyl ...
3738-00-9 Process route
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(d,l)-8α,12-epoxy-3β-hydroxy-13,14,15,16-tetranorlabdane
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3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6
(±)-ambrox
| Conditions | Yield |
|---|---|
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(d,l)-8α,12-epoxy-3β-hydroxy-13,14,15,16-tetranorlabdane;
With
dmap; pentafluorophenoxythiocarbonyl chloride;
In
dichloromethane;
at 0 - 20 ℃;
for 4h;
With
2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride;
In
benzene;
for 3h;
Reflux;
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74% |
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Multi-step reaction with 2 steps
1: 98 percent / trifluoromethanesulfonyl chloride, 4-DMAP / CH2Cl2 / 7 h / 0 °C
2: 100 percent / H2 / Pd/C / methanol / 760 Torr
With
dmap; trifluoromethane sulfonyl chloride; hydrogen;
palladium on activated charcoal;
In
methanol; dichloromethane;
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(d,l)-13,14,15,16-tetranor-8α,12-epoxy-2-labdene
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3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6
(±)-ambrox
| Conditions | Yield |
|---|---|
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With
hydrogen;
palladium on activated charcoal;
In
methanol;
under 760 Torr;
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100% |
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