Molecules

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Synthesis of the Demospongic Compounds, (6Z, 11Z)-Octadecadienoic Acid and (6Z, 11Z)-Eicosadienoic Acid

by B. A. Kulkarni, S. Chattopadhyay, A. Chattopadhyay and V. R. Mamdapur

Molecules 1997, 2(6), 99; https://doi.org/10.3390/20600099 - 30 Jun 1997

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Abstract

n/a Full article

88 KiB

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[3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diyl Diacetate

by Margaret A. Brimble and Andrew D. Johnston

Molecules 1997, 2(6), M22; https://doi.org/10.3390/M22 - 20 Jun 1997

Viewed by 3731

Abstract

To a solution of [3S*,5S*,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (1) [1] (33 mg, 0.17 mmol) in dichloromethane (10 ml) was added triethylamine (54 mg, 0.53 mmol), acetic anhydride (34 mg, 0.34 mmol) and 4-dimethylaminopyridine (3 mg).[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

80 KiB

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[4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undec-4,5-diyl Diacetate

by Margaret A. Brimble and Andrew D. Johnston

Molecules 1997, 2(6), M21; https://doi.org/10.3390/M21 - 20 Jun 1997

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Abstract

To a solution of [4R*,5R*,6S*]-1,7-dioxaspiro[5.5]undecane-4,5-diol (1) (50 mg, 0.27 mmol) in dichloromethane (10 ml) was added triethylamine (100 mg, 0.99 mmol), acetic anhydride (67 mg, 0.66 mmol) and 4-dimethylaminopyridine (3 mg).[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

80 KiB

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[3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diol

by Margaret A. Brimble and Andrew D. Johnston

Molecules 1997, 2(6), M20; https://doi.org/10.3390/M20 - 20 Jun 1997

Cited by 2 | Viewed by 3841

Abstract

The reaction and the product ratio shown in the scheme was reported [1].[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

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Scheme 1

85 KiB

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[4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undecane-4,5-diol

by Margaret A Brimble and Andrew D Johnston

Molecules 1997, 2(6), M19; https://doi.org/10.3390/M19 - 20 Jun 1997

Cited by 1 | Viewed by 3909

Abstract

A solution of [3R*,4R*,5S*,6S*]-3,4-epoxy-1,7-dioxaspiro[5.5]undecan-5-ol (1) (561 mg, 3.01mmol) in dry tetrahydrofuran (30 ml) under a nitrogen atmosphere was cooled to 0 deg.C in an ice/water bath.[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

89 KiB

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[3R*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diyl Bis(3,5-dinitrobenzoate)

by Margaret A. Brimble and Andrew D. Johnston

Molecules 1997, 2(6), M18; https://doi.org/10.3390/M18 - 20 Jun 1997

Viewed by 3861

Abstract

To a solution of [3R*,5S8,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (50 mg, 0.27 mmol) in dichloromethane (5.0 cm3), was added triethylamine (60 mg, 0.59 mmol), 4-dimethylaminopyridine (~1 mg), 3,5-dinitrobenzoyl chloride (136 mg, 0.59 mmol) and the resultant solution allowed to stand at room temperature for 120 h.[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

83 KiB

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[3R*,5S*,6S*]-5-Hydroxy-1,7-dioxaspiro[5.5]undec-3-yl 3,5-Dinitrobenzoate

by Margaret A. Brimble and Andrew D. Johnston

Molecules 1997, 2(6), M17; https://doi.org/10.3390/M17 - 20 Jun 1997

Viewed by 3614

Abstract

To a solution of [3R*,5S8,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (50 mg, 0.27 mmol) in dichloromethane (5.0 ml), was added triethylamine (56 mg, 0.55 mmol), 4-dimethylaminopyridine (~1 mg), and 3,5-dinitrobenzoyl chloride (64 mg, 0.28 mmol) and the resultant solution allowed to stand [...] Read more.

To a solution of [3R*,5S8,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (50 mg, 0.27 mmol) in dichloromethane (5.0 ml), was added triethylamine (56 mg, 0.55 mmol), 4-dimethylaminopyridine (~1 mg), and 3,5-dinitrobenzoyl chloride (64 mg, 0.28 mmol) and the resultant solution allowed to stand at room temperature for 48 h.[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

81 KiB

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[2R*,5S*,6S*]-2-Methyl-1,7-dioxaspiro[5.5]undec-2-en-5-ol

by Margaret A. Brimble and Andrew D. Johnston

Molecules 1997, 2(6), M16; https://doi.org/10.3390/M16 - 20 Jun 1997

Cited by 1 | Viewed by 3659

Abstract

The reaction and the product ratio shown in the scheme was reported [1] [...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

101 KiB

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[2R*,5S*,6S*]-2-Methyl-1,7-dioxaspiro[5.5]undec-3-en-5-ol§

by Margaret A. Brimble and Andrew D. Johnston

Molecules 1997, 2(6), M15; https://doi.org/10.3390/M15 - 20 Jun 1997

Cited by 1 | Viewed by 3661

Abstract

Isomerisations of epoxides to allylic alcohols have been effected by strong non-nucleophilic bases such as lithium dialkylamides.[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

103 KiB

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2-Ethyl-1-hydroxymethyl-4-trifluoromethyl-9H-carbazole

by Norbert Haider and Richard Wanko

Molecules 1997, 2(6), M14; https://doi.org/10.3390/M14 - 16 Jun 1997

Viewed by 3138

Abstract

The general part of the experimental section [1] has been presented elsewhere.[...] Full article

(This article belongs to the Section Molbank Section of Molecules, 1997-2001)

45 KiB

Open AccessArticle

Synthesis and Characterization of Heptamethine Cyanine Dyes

by Qun Li, Ji Tan and Bi-Xian Peng

Molecules 1997, 2(6), 91-98; https://doi.org/10.3390/20600091 - 11 Jun 1997

Cited by 22 | Viewed by 13380

Abstract

A series of meso-chlorine substituted heptamethine-cyanine dyes and related heptamethine cyanine dyes unsubstituted on the vinyl chain were synthesized by condensation of 2,3,3-trimethyl indolenium salts with reactive intermediates, 2-chloro-formyl-3-hydroxy-methylenecyclohexene or N-[5-(phenylamino)-2,4-phentadienylidene] aniline monohydro-c hloride. The structures of the dyes were characterized by virtue [...] Read more.

A series of meso-chlorine substituted heptamethine-cyanine dyes and related heptamethine cyanine dyes unsubstituted on the vinyl chain were synthesized by condensation of 2,3,3-trimethyl indolenium salts with reactive intermediates, 2-chloro-formyl-3-hydroxy-methylenecyclohexene or N-[5-(phenylamino)-2,4-phentadienylidene] aniline monohydro-c hloride. The structures of the dyes were characterized by virtue of ¹HNMR, ¹³C-NMR, IR, MS, etc. The reaction conditions and physicochemical properties of the dyes were extensively explored with classical photo-physical techniques Full article

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Scheme 1

23 KiB

Open AccessArticle

10-Undecenoic Acid, an Inexpensive Source for the Synthesis of the Pheromones of Cotton Pests, Peach Tree Borer and Cherry Tree Borer

by Archana S. Pawar and Subrata Chattopadhyay

Molecules 1997, 2(6), 87-90; https://doi.org/10.3390/20600087 - 10 Jun 1997

Cited by 6 | Viewed by 8296

Abstract

The aldehyde 7, derived from 10-undecenoic acid (5) on cis-selective Wittig reaction with pentylidenetriphenylphosphorane, subsequent deprotection and oxidation gave the pheromone (11Z)-hexadecenal (1). Wittig-Horner olefination of 1 with the phosphonate 9 furnished the conjugated ester 10 which on base catalyzed isomerization to [...] Read more.

The aldehyde 7, derived from 10-undecenoic acid (5) on cis-selective Wittig reaction with pentylidenetriphenylphosphorane, subsequent deprotection and oxidation gave the pheromone (11Z)-hexadecenal (1). Wittig-Horner olefination of 1 with the phosphonate 9 furnished the conjugated ester 10 which on base catalyzed isomerization to the (3Z)-ester 11 followed by LAH reduction and acetylation gave (3Z,13Z)-octadeadien-1-yl acetate (2). Compound 10 on the other hand was chemoselectively reduced and acetylated to furnish the pheromone (2E,13Z)-octadeadien-1-yl acetate (4). For the synthesis of (3E,13Z)-octadeadien-1-yl acetate (3), 1 was condensed with malonic acid under modified condition to afford the acid 13 which was converted to 3 by standard reaction protocol. Full article

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Molecules, Volume 2, Issue 6 (June 1997) – 12 articles , Pages 87-99, Articles M14-M22

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