MD4248C1 - Способ получения 14,15-биснорлабдан-8(9)-ен-13-она - Google Patents
Способ получения 14,15-биснорлабдан-8(9)-ен-13-онаInfo
- Publication number
- MD4248C1 MD4248C1 MDA20130021A MD20130021A MD4248C1 MD 4248 C1 MD4248 C1 MD 4248C1 MD A20130021 A MDA20130021 A MD A20130021A MD 20130021 A MD20130021 A MD 20130021A MD 4248 C1 MD4248 C1 MD 4248C1
- Authority
- MD
- Moldova
- Prior art keywords
- bisnorlabdan
- hydroxyketone
- reaction
- solution
- producing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 238000004809 thin layer chromatography Methods 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 3
- NTJPIRDYMVYFNP-UHFFFAOYSA-M trimethylsilylmethanesulfonate Chemical compound C[Si](C)(C)CS([O-])(=O)=O NTJPIRDYMVYFNP-UHFFFAOYSA-M 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 150000003505 terpenes Chemical class 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- -1 acetonitrile trimethylsilylmethanesulfonate Chemical compound 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Изобретение относится к органической химии, в частности к способу получения 14,15-биснорлабдан-8(9)-ен-13-она (2) - важного и ценного промежуточного соединения для синтеза дримановых сесквитерпеноидов и высших терпеноидов.Способ включает обработку раствора гидроксикетона (1) в ацетонитриле триметилсилилметансульфонатом, взятом в молярном избытке 1:5, при комнатной температуре:При этом ход реакции контролируется методом тонкослойной хроматографии.Технический результат изобретения состоит в разработке воспроизводимого, более быстрого и с большим выходом способа получения 14,15-биснорлабдан-8(9)-ен-13-она.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20130021A MD4248C1 (ru) | 2013-04-19 | 2013-04-19 | Способ получения 14,15-биснорлабдан-8(9)-ен-13-она |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20130021A MD4248C1 (ru) | 2013-04-19 | 2013-04-19 | Способ получения 14,15-биснорлабдан-8(9)-ен-13-она |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4248B1 MD4248B1 (en) | 2013-08-31 |
| MD4248C1 true MD4248C1 (ru) | 2014-03-31 |
Family
ID=49117533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20130021A MD4248C1 (ru) | 2013-04-19 | 2013-04-19 | Способ получения 14,15-биснорлабдан-8(9)-ен-13-она |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4248C1 (ru) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD2019B2 (en) * | 2001-02-22 | 2002-10-31 | Inst De Chimie Al Academiei De | Process for obtaining of 8a-acetoxy-14,15-bisnorlabdan-13-one from sclareol diacetate |
| MD3273G2 (ru) * | 2006-07-14 | 2007-10-31 | Институт Химии Академии Наук Молдовы | Способ получения ацетата дрименола из 11-моноацетата дриман-8а,11-диола |
| MD3889C2 (ru) * | 2008-05-19 | 2009-11-30 | Институт Химии Академии Наук Молдовы | Способ получения 11-бисгомодрим-8(9)-ен-12-она |
-
2013
- 2013-04-19 MD MDA20130021A patent/MD4248C1/ru not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD2019B2 (en) * | 2001-02-22 | 2002-10-31 | Inst De Chimie Al Academiei De | Process for obtaining of 8a-acetoxy-14,15-bisnorlabdan-13-one from sclareol diacetate |
| MD3273G2 (ru) * | 2006-07-14 | 2007-10-31 | Институт Химии Академии Наук Молдовы | Способ получения ацетата дрименола из 11-моноацетата дриман-8а,11-диола |
| MD3889C2 (ru) * | 2008-05-19 | 2009-11-30 | Институт Химии Академии Наук Молдовы | Способ получения 11-бисгомодрим-8(9)-ен-12-она |
Non-Patent Citations (2)
| Title |
|---|
| Hua S.-K., Wang J., Chen X.-B., Xu Z.-Yu, Zeng B.-B. Tetrahedron 2011, No. 67, p. 1142-1144 * |
| Marcos I.S., Lourdes-Castaneda A.B., Moro R.F., David Diez P.B., Urones J.G. Synlett, 2007, No. 10, p. 1598-1590 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4248B1 (en) | 2013-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |