1-Naphthalenepropanol,.alp

Base Information

• Chemical Name: 1-Naphthalenepropanol,.alp
• CAS No.: 1438-62-6
• Molecular Formula: C20H34 O
• Molecular Weight: 290.489
• Mol file: 1438-62-6.mol

Synonyms:1-Naphthalenepropanol,a-ethenyldecahydro-a,5,5,8a-tetramethyl-2-methylene-,[1S-[1a(R*),4ab,8aa]]-; Labda-8(20),14-dien-13-ol, (13S)- (8CI);(13S)-Manool; 13-Epimanool; 13-epi-Manool; Epimanool; epi-13-Manool

Chemical Property of 1-Naphthalenepropanol,.alp

Chemical Property:

• Melting Point: 35-38 °C
• Boiling Point: 368.2±11.0 °C(Predicted)
• PKA: 14.47±0.29(Predicted)
• PSA: 20.23000
• Density: 0.93±0.1 g/cm3(Predicted)
• LogP: 5.50240

Purity/Quality:

98% ^*data from raw suppliers

13-Epimanool 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Naphthalenepropanol,.alp

There total 15 articles about 1-Naphthalenepropanol,.alp 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: 82.0%

Toluene-4-sulfonic acid (2R,4aR,5S,8aR)-5-((S)-3-hydroxy-3-methyl-pent-4-enyl)-1,1,4a-trimethyl-6-methylene-decahydro-naphthalen-2-yl ester → (+)-manool (596-85-0,29461-42-5,41357-91-9,106631-38-3,1438-62-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

Reference yield: 40.0%

(E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8) → (+)-manool (596-85-0,29461-42-5,41357-91-9,106631-38-3,1438-62-6) + manool (596-85-0) + 8(17),13(E)-labdadien-15-ol (10395-43-4)

Guidance literature:

With DL-dithiothreitol; recombinant (+)-copalyl diphosphate synthase-GST fusion protein; recombinant Rv₃₃₇₈c enzyme from Mycobacterium tuberculosis; magnesium chloride; at 30 ℃; for 15h; pH=7.5; diastereoselective reaction; aq. buffer; Enzymatic reaction;

DOI:10.1039/c0ob00884b

Reference yield: 40.0%

labda-8(17),13-diene (10483-51-9) → 13-epimanool (1438-62-6) + epimanool (596-85-0) + labda-8(17),13(16)-dien-14-ol (19884-99-2,61091-79-0,61091-80-3)

Guidance literature:

With oxygen; rose bengal; triethyl phosphite; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) CH₂Cl₂, CH₃OH, irradiation, 90 min;

DOI:10.1021/jo00320a027

upstream raw materials:

3-oxo-8⁽¹⁷⁾-labdadien-13R-ol

sclareol

8⁽¹⁷⁾-labdadien-3R,13R-diol

(E,E,E)-geranylgeranyl diphosphate

Downstream raw materials:

4-Methoxy-2-[(E)-3-methyl-5-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enyl]-phenol

manoyl oxide

4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one

7-(5,5,8a-trimethyl-2-methylenedecahydronaphthyl)-5-methyl-hept-4-enal

Refernces

• 1、 Agarwal, S. G.,Thappa, R. K.,Dhar, K. L.. "Oxidation studies on 8(17),14-labdadien-3R,13R-diol: A major diterpene of Juniperus pseudosabina Hook". . p. 669 - 671. Retrieved 2007/10/03.
• 2、 Hieda, Tadaharu,Mikami, Yoichi,Obi, Yukiteru,Kisaki, Takuro. "Plasmid-determined Transformation of cis Abienol and Sclareol in Nocardia restricta JTS-162". . p. 3055 - 3062. Retrieved 2007/10/02.