e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

On the regioselectivity of elimination reactions in terpene derivatives

B Badet, M Julia, JM Mallet, C Schmitz

Index: Badet,B.; Julia,M.; Mallet,J.M. Tetrahedron, 1988 , vol. 44, p. 2913

Full Text: HTML

Citation Number: 8

Abstract

Tertiary alcohols with prenyl or geranyl moities, bearing a second oxygen. function in the 3, 4 or 5 position were dehydrated under various conditions: the composition of the olefinic mixture obtained was accounted for, by an intramolecular base relay effect. Basic elimination of analogous dimethylsutfonium salts gave results that could be related to the inductive effect: a correlation between regioselectivity and the Taft constantσI of the ...

2-acetoxy-6-methyl-6-heptene Structure

2-acetoxy-6-met...

~%

UNII:W5970P28N3 Structure

UNII:W5970P28N3

dimethyl-5-hexen-1-yl acetate Structure

dimethyl-5-hexe...

2-acetoxy-6-methyl-6-heptene Structure

2-acetoxy-6-met...

~%

UNII:W5970P28N3 Structure

UNII:W5970P28N3

2-acetoxy-6-methyl-6-heptene Structure

2-acetoxy-6-met...

~%

UNII:W5970P28N3 Structure

UNII:W5970P28N3

dimethyl-5-hexen-1-yl acetate Structure

dimethyl-5-hexe...

2-Methyl-2,4-butanediol Structure

2-Methyl-2,4-bu...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

O-Acetyl-2-methylpentane-2,5-diol Structure

O-Acetyl-2-meth...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

6-Methylhept-5-en-2-one Structure

6-Methylhept-5-...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

4,8-dimethyl-7-nonene-1,4-diol Structure

4,8-dimethyl-7-...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

1-acetoxy-4,8-dimethyl-7-nonen-4-ol Structure

1-acetoxy-4,8-d...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

(E)-4,8-dimethylnona-4,7-dien-1-yl acetate Structure

(E)-4,8-dimethy...

(Z)-4,8-dimethylnona-3,7-dien-1-yl acetate Structure

(Z)-4,8-dimethy...

Detail

4-methylpentane-1,4-diol Structure

4-methylpentane...

~0%

2,2-dimethyltetrahydrofuran Structure

2,2-dimethyltet...

4-methyl-3-penten-1-ol Structure

4-methyl-3-pent...

4-Methyl-4-penten-1-ol Structure

4-Methyl-4-pent...

2-Methyl-1-octene Structure

2-Methyl-1-octene

~%

2-METHYL-2-OCTENE Structure

2-METHYL-2-OCTENE

2-Octanol, 2-methyl- Structure

2-Octanol, 2-methyl-

~%

2-METHYL-2-OCTENE Structure

2-METHYL-2-OCTENE

2-Methyl-1-octene Structure

2-Methyl-1-octene

ISOPRENOL Structure

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

~%

(±)-3,7-dimethyloct-6-ene-1,3-diol Structure

(±)-3,7-dimethy...

7-Methyl-3-methylene-6-octen-1-ol Structure

7-Methyl-3-meth...

Detail

3-Buten-1-ol,3-methyl-, 1-(4-methylbenzenesulfonate) Structure

3-Buten-1-ol,3-...

~%

5-Methyl-5-hexenoic acid methyl ester Structure

5-Methyl-5-hexe...

2-Octanol, 2-methyl- Structure

2-Octanol, 2-methyl-

~%

2-METHYL-2-OCTENE Structure

2-METHYL-2-OCTENE

2-Methyl-1-octene Structure

2-Methyl-1-octene

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

dimethyl-5-hexen-1-yl acetate Structure

dimethyl-5-hexe...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

tangerine acetate Structure

tangerine acetate

Detail

2-Methyl-2,4-butanediol Structure

2-Methyl-2,4-bu...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

2-acetoxy-6-methyl-6-heptene Structure

2-acetoxy-6-met...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

5-Chloro-2-pentanol Structure

5-Chloro-2-pentanol

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

6-Methylhept-5-en-2-one Structure

6-Methylhept-5-...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

dimethyl-5-hexen-1-yl acetate Structure

dimethyl-5-hexe...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

6,10-dimethyl-9-undecene-2,6-diol Structure

6,10-dimethyl-9...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

1-acetoxy-6,10-dimethyl-9-undecen-6-ol Structure

1-acetoxy-6,10-...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

tangerine acetate Structure

tangerine acetate

(E)-6,10-dimethylundeca-6,9-dien-2-yl acetate Structure

(E)-6,10-dimeth...

Detail

4-(2-chloro-1,1,2-trifluoroethoxy)-2-methylbut-1-ene Structure

4-(2-chloro-1,1...

~%

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methylbut-2-ene Structure

1-(2-chloro-1,1...

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methyl-3-butanol Structure

1-(2-chloro-1,1...

~%

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methylbut-2-ene Structure

1-(2-chloro-1,1...

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methyl-3-butanol Structure

1-(2-chloro-1,1...

~%

4-(2-chloro-1,1,2-trifluoroethoxy)-2-methylbut-1-ene Structure

4-(2-chloro-1,1...

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methylbut-2-ene Structure

1-(2-chloro-1,1...

2-methylheptane-2,6-diol Structure

2-methylheptane...

~%

tetrahydro-2,2,6-trimethyl-2H-pyran Structure

tetrahydro-2,2,...

sulcatol Structure

6-methylhept-6-en-2-ol Structure

6-methylhept-6-...

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methyl-3-butanol Structure

1-(2-chloro-1,1...

~%

4-(2-chloro-1,1,2-trifluoroethoxy)-2-methylbut-1-ene Structure

4-(2-chloro-1,1...

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methylbut-2-ene Structure

1-(2-chloro-1,1...

4-methylpent-4-enoxybenzene Structure

4-methylpent-4-...

~%

4-methylpent-3-enoxybenzene Structure

4-methylpent-3-...

4-methylpentane-1,4-diol Structure

4-methylpentane...

~%

4-methylpent-3-enoxybenzene Structure

4-methylpent-3-...

4-methyl-3-penten-1-ol Structure

4-methyl-3-pent...

Phenol Structure

~48%

4-methylpent-3-enoxybenzene Structure

4-methylpent-3-...

4-Methyl-4-penten-1-ol Structure

4-Methyl-4-pent...

~%

4-methylpent-3-enoxybenzene Structure

4-methylpent-3-...

2-methylheptane-2,6-diol Structure

2-methylheptane...

~%

tetrahydro-2,2,6-trimethyl-2H-pyran Structure

tetrahydro-2,2,...

sulcatol Structure

6-methylhept-6-en-2-ol Structure

6-methylhept-6-...

1-butoxy-3-methyl-3-butanol Structure

1-butoxy-3-meth...

~%

4-butoxy-2-methylbut-1-ene Structure

4-butoxy-2-meth...

2-Butene, 1-butoxy-3-methyl- Structure

2-Butene, 1-but...

4-Methyl-4-penten-1-ol Structure

4-Methyl-4-pent...

Phenol Structure

~47%

4-methylpent-4-enoxybenzene Structure

4-methylpent-4-...

4-methylpentane-1,4-diol Structure

4-methylpentane...

~%

4-methylpent-4-enoxybenzene Structure

4-methylpent-4-...

2-methylheptane-2,6-diol Structure

2-methylheptane...

~%

6-methylhept-5-en-2-yloxybenzene Structure

6-methylhept-5-...

6-methylhept-6-en-2-yloxybenzene Structure

6-methylhept-6-...

~%

6-methylhept-5-en-2-yloxybenzene Structure

6-methylhept-5-...

6-methylhept-6-en-2-ol Structure

6-methylhept-6-...

~%

6-methylhept-5-en-2-yloxybenzene Structure

6-methylhept-5-...

sulcatol Structure

Phenol Structure

~53%

6-methylhept-5-en-2-yloxybenzene Structure

6-methylhept-5-...

O-Acetyl-2-methylpentane-2,5-diol Structure

O-Acetyl-2-meth...

~%

acetic acid,4-methylpent-3-en-1-ol Structure

acetic acid,4-m...

4-methylpentane-1,4-diol Structure

4-methylpentane...

~63%

2,2-dimethyltetrahydrofuran Structure

2,2-dimethyltet...

4-methyl-3-penten-1-ol Structure

4-methyl-3-pent...

4-Methyl-4-penten-1-ol Structure

4-Methyl-4-pent...

1-Acetoxy-3-methyl-3-butanol Structure

1-Acetoxy-3-met...

~%

Prenyl acetate Structure

isoprenyl acetate Structure

isoprenyl acetate

ISOPRENOL Structure

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

~%

(±)-3,7-dimethyloct-6-ene-1,3-diol Structure

(±)-3,7-dimethy...

7-Methyl-3-methylene-6-octen-1-ol Structure

7-Methyl-3-meth...

Detail

6-methylhept-6-en-2-ol Structure

6-methylhept-6-...

Phenol Structure

~52%

6-methylhept-6-en-2-yloxybenzene Structure

6-methylhept-6-...

2-methylheptane-2,6-diol Structure

2-methylheptane...

~%

6-methylhept-6-en-2-yloxybenzene Structure

6-methylhept-6-...

Prenylation of isopentenyl derivatives with 2-methyl-3-buten...

[Julia, M.; Schmitz, C. Bulletin de la Societe Chimique de France, 1986 , # 4 p. 630 - 636]