cassaine

Base Information

• Chemical Name: cassaine
• CAS No.: 468-76-8
• Molecular Formula: C₂₄H₃₉NO₄
• Molecular Weight: 405.578
• Mol file: 468-76-8.mol

Synonyms:Acetic acid,(dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene)-,2-(dimethylamino)ethyl ester, [1R-(1a,2E,4aa,4bb,7b,8aa,10ab)]-; Cassaine (6CI,7CI);Podocarpane-D13,a-acetic acid, 3b-hydroxy-14a-methyl-7-oxo-,2-(dimethylamino)ethyl ester, (E)- (8CI); (+)-Cassaine

Chemical Property of cassaine

Chemical Property:

• Vapor Pressure: 6.87E-13mmHg at 25°C
• Melting Point: 142.5°
• Boiling Point: 517.9°Cat760mmHg
• PKA: 15.04±0.70(Predicted)
• Flash Point: 267°C
• PSA: 66.84000
• Density: 1.093g/cm³
• LogP: 3.45610

Purity/Quality:

CASSAINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cassaine

There total 45 articles about cassaine 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: 76.0%

(E)-2-(dimethylamino)ethyl 2-((1R,4aS,4bR,7S,8aR,10aS)-7-(methoxymethoxy)-1,4b,8,8-tetramethyl-10-oxododecahydrophenanthren-2(3H)-ylidene)acetate (1072195-29-9) → Cassaine (468-76-8)

Guidance literature:

With lithium tetrafluoroborate; water; In acetonitrile; at 75 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja805097s

Reference yield:

(2S,4aS,7S,8aR)-2-(benzyloxy)-1,1,4a-trimethyl-7-(prop-1-en-2-yl)decahydronaphthalene (1492141-97-5) → Cassaine (468-76-8)

Guidance literature:

Multi-step reaction with 28 steps

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 20 °C

2.1: silica gel-NaIO₄ / dichloromethane / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 16 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / methanol / 16 h / 20 °C / Inert atmosphere

5.1: dipyridinium dichromate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

6.1: sodium hydride; potassium hydride / mineral oil; tetrahydrofuran / 2 h / Inert atmosphere; Reflux

7.1: pyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

7.2: 2 h / 0 - 20 °C / Inert atmosphere

7.3: 0.25 h

8.1: caesium carbonate / ethyl acetate / 24 h / 20 °C / Inert atmosphere

9.1: sodium ethanolate / ethanol / 2 h / 20 °C / Inert atmosphere

10.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / -78 °C / Inert atmosphere

11.1: 1H-imidazole; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

12.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / 775.74 Torr

13.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere

14.1: lithium; ammonia / tert-butyl alcohol; tetrahydrofuran / 2 h / -33 °C

15.1: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; tetrahydrofuran / Inert atmosphere; Reflux

16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

17.1: dipyridinium dichromate; pyridine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

18.1: sodium hydride; potassium hydride / mineral oil; tetrahydrofuran / 2 h / Inert atmosphere; Reflux

19.1: sodium tetrahydroborate / ethanol / -10 °C / Inert atmosphere

20.1: pyridine; thionyl chloride / 1 h / 0 - 20 °C / Inert atmosphere

21.1: magnesium / methanol / 5 h / 20 °C / Inert atmosphere

22.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

23.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

24.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

24.2: -78 - 0 °C / Inert atmosphere

25.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 3 h / 20 °C / Inert atmosphere

26.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

27.1: potassium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride / 1-methyl-pyrrolidin-2-one / 16 h / 100 °C / 5171.62 Torr

28.1: lithium tetrafluoroborate; water / acetonitrile / 16 h / 75 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; osmium(VIII) oxide; dipyridinium dichromate; lithium tetrafluoroborate; thionyl chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; sodium ethanolate; tetra-(n-butyl)ammonium iodide; lithium; potassium hydride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; magnesium; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil; tert-butyl alcohol; 14.1: |Birch Reduction;

DOI:10.1021/ol4030937

Reference yield:

C23H36O3 (1569079-85-1) → Cassaine (468-76-8)

Guidance literature:

Multi-step reaction with 27 steps

1.1: silica gel-NaIO₄ / dichloromethane / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / methanol / 16 h / 20 °C / Inert atmosphere

4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

5.1: sodium hydride; potassium hydride / mineral oil; tetrahydrofuran / 2 h / Inert atmosphere; Reflux

6.1: pyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

6.2: 2 h / 0 - 20 °C / Inert atmosphere

6.3: 0.25 h

7.1: caesium carbonate / ethyl acetate / 24 h / 20 °C / Inert atmosphere

8.1: sodium ethanolate / ethanol / 2 h / 20 °C / Inert atmosphere

9.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.17 h / -78 °C / Inert atmosphere

10.1: 1H-imidazole; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

11.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / 775.74 Torr

12.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere

13.1: lithium; ammonia / tert-butyl alcohol; tetrahydrofuran / 2 h / -33 °C

14.1: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; tetrahydrofuran / Inert atmosphere; Reflux

15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

16.1: dipyridinium dichromate; pyridine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

17.1: sodium hydride; potassium hydride / mineral oil; tetrahydrofuran / 2 h / Inert atmosphere; Reflux

18.1: sodium tetrahydroborate / ethanol / -10 °C / Inert atmosphere

19.1: pyridine; thionyl chloride / 1 h / 0 - 20 °C / Inert atmosphere

20.1: magnesium / methanol / 5 h / 20 °C / Inert atmosphere

21.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

22.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

23.1: potassium hexamethylsilazane / toluene; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

23.2: -78 - 0 °C / Inert atmosphere

24.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 3 h / 20 °C / Inert atmosphere

25.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

26.1: potassium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride / 1-methyl-pyrrolidin-2-one / 16 h / 100 °C / 5171.62 Torr

27.1: lithium tetrafluoroborate; water / acetonitrile / 16 h / 75 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; dipyridinium dichromate; lithium tetrafluoroborate; thionyl chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; sodium ethanolate; tetra-(n-butyl)ammonium iodide; lithium; potassium hydride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; magnesium; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol; 13.1: |Birch Reduction;

DOI:10.1021/ol4030937

upstream raw materials:

2-(dimethylamino)ethyl chloride

(E)-2-(dimethylamino)ethyl 2-((1R,4aS,4bR,7S,8aR,10aS)-7-(methoxymethoxy)-1,4b,8,8-tetramethyl-10-oxododecahydrophenanthren-2(3H)-ylidene)acetate

(2S,4aS,7S,8aR)-2-(benzyloxy)-1,1,4a-trimethyl-7-(prop-1-en-2-yl)decahydronaphthalene

C₂₃H₃₆O₃

Downstream raw materials:

Cassainsaeure

(3β-hydroxy-7-oxo-14α-methyl-podocarpanyl-(13α))-acetic acid

Refernces

• 1、 Ravindar, Kontham,Caron, Pierre-Yves,Deslongchamps, Pierre. "Total synthesis of (+)-cassaine utilizing an anionic polycyclization strategy". supporting information. p. 6270 - 6273. Retrieved 2014/01/17.