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)

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 3636

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)

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 3699

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)

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 3629

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

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

Viewed by 3417

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)

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 3505

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)

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 8012

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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Scheme 1

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 12846

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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