106818-49-9

Basic information

• Product Name: 15-hydroxydihydrokaurenoic acid methyl ester
• Synonyms: 15-hydroxydihydrokaurenoic acid methyl ester
• CAS NO: 106818-49-9
• Molecular Formula: C21H34O3
• Molecular Weight: 334.49286
• Mol File: 106818-49-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 425.6°Cat760mmHg
• Flash Point: 163.8°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 5E-09mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: 15-hydroxydihydrokaurenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 15-hydroxydihydrokaurenoic acid methyl ester(106818-49-9)
• EPA Substance Registry System: 15-hydroxydihydrokaurenoic acid methyl ester(106818-49-9)

Safety Data

• Hazardous Substances Data: 106818-49-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H34O3/c1-13-14-6-7-16-19(2)9-5-10-20(3,18(23)24-4)15(19)8-11-21(16,12-14)17(13)22/h13-17,22H,5-12H2,1-4H3/t13?,14?,15-,16-,17?,19+,20+,21?/m0/s1

Upstream product

• 36100-66-0 (-)-4α-kaura-9(11),16-dien-19-oic acid methyl ester 
• 18671-79-9 methyl ent-kaur-15-en-19-oate 
• 5524-25-4 kaurenoic acid methyl ester 
• 5095-09-0 kaurenoic acid 
• 22343-41-5 methyl ent-15β-hydroxy-kaur-16-en-19-oate 
• 22376-47-2 methyl ent-15-oxokaur-16-en-19-oate 
• 6619-96-1 Methyl 15β-hydroxy-ent-kaur-16-en-19-oate 
• 78037-84-0 methyl ent-15-oxokauran-19-oate 
• 78037-83-9 methyl ent-15α-acetoxykauran-19-oate 
• 6619-98-3 methyl xylopate 
• 6619-97-2 15β–acetoxy–(–)–kaur–16–en–l9–oic acid 
• 250718-32-2 methyl ent-15β-hydroxy-16α-kauran-19-oate 

Downstream Products

• 77970-49-1 methyl ent-15α-hydroxykauran-19-oate 
• 78037-84-0 methyl ent-15-oxokauran-19-oate 

Relevant articles and documents

Fluorinated Kaurenoids. Part 2. Preparation of Methyl ent-17,17,17-Trifluorokaur-15-en-19-oate and ent-16,16-Difluoro-17-norkauran-19-oic Acid from Xylopic Acid

An attempt to convert methyl ent-16-oxo-17-norkauran-19-oate (3), derived from xylopic acid, into methyl ent-17,17-difluorokaur-16-en-19-oate failed.However, treatment of the norketone (3) with diethylaminosulphurtrifluoride (DAST) gave methyl ent-16,16-difluoro-17-norkauran-19-oate (5).The latter afforded the corresponding acid (4) which was active as a growth promoter in a dwarf-rice bioassay.Treatment of methyl deacetylxylopate (18) with DAST, followed by cleavage of the terminal methylene group, yielded methyl ent-15-fluoro-16-oxo-17-norkauran-19-oate (15), which on reaction with dibromodifluoromethane and tris(dimethylamino)phosphine gave, not the expected 17,17-difluoro-olefin (19), but methyl ent-17,17,17-frifluorokaur-15-en-19-oate (28) in poor yield.Reduction of methyl xylopate with di-imide gave the 16β-methyl compound (24) stereospecifically.The latter was readily converted into methyl 15-oxokauranoate (26), but steric hindrance prevented the reaction of the oxo-group with DAST to give the 15,15-difluoride, under normal reaction conditions; using a much longer reaction time a trace of the gem-difluoride was formed.During reduction of the dithiocarbonate (27) of methyl deacetylxylopate with tri-n-butyltin hydride into the isomeric methyl kaurenoates (8) and (31), the 17-thiol ester (32) was also formed by a sigmatropic rearrangement.

Fluorination of kaurenoic acid derivatives by remote functionalization

Kauranoids and related tetracyclic diterpenoids have recently shown an increasing interest because of the discovery of new biological activities that can be modified by the introduction of a fluorine atom. In this article it is described the stereospecific fluorination of the kauranols 6 and 7 by remote functionalization at the 'unactivated' C-7 position.