(+)-trans-camphenesulfonamide: A novel enantiomerically pure primary sulfonamide

Davis, Franklin A.; Boyd, Robert L.; Zhou, Ping; Abdul-Malik, Nadia Fouad; Carroll, Patrick J.

doi:10.1016/0040-4039(96)00567-9

Cited by 6 publications

(3 citation statements)

References 7 publications

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“…2. The same one-dimensional structure has been found previously in only a few other compounds of the sulfonamide class, see Davis et al (1996) The sulfonyl oxygen atom O2 accepts an additional H-bond from the NH group of a neighbouring molecule. This interaction links molecules which are related to one another by a 2 1 operation parallel to the c-axis (see Fig.…”

Section: S1 Commentsupporting

confidence: 75%

“…For the pharmacology and synthesis of the title compound, see Goissedet et al (1936); Goissedet & Despois (1938); Mellon et al (1938); Long & Bliss (1939). For related structures, see: Hursthouse et al (1998Hursthouse et al ( , 1999a; Gelbrich et al (2008); Davis et al (1996); Costanzo et al (1999); Kubicki & Codding (2001); Yathirajan et al (2005); Denehy et al (2006); Toumieux et al (2006). For graph-set analysis, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

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Benzylsulfamide

2011

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The crystal of the title compound [systematic name: 4-(benzylamino)benzenesulfonamide], C13H14N2O2S, displays a hydrogen-bonded framework structure. Molecules are doubly N—H⋯O hydrogen bonded to one another via their NH2 groups and sulfonyl O atoms. These interactions generate a hydrogen-bonded ladder structure parallel to the a axis, which contains fused R 2 2(8) rings. The NH group serves as the hydrogen-bond donor for a second set of intermolecular N—H⋯O=S interactions.

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Section: S1 Commentsupporting

confidence: 75%

Section: Related Literaturementioning

confidence: 99%

Benzylsulfamide

2011

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“…539 The sulfonamide 415 undergoes acid-catalysed rearrangement to yield the enantiomerically pure primary sulfonamide 416. 540 Full details of preparations of the camphorsulfonyloxaziridines 417, and protocols for their application in enantioselective oxidation reactions of some tetralone derivatives have been reported. 541 A number of optically pure Te-chiral alkoxytelluranes 418 have been prepared, and an X-ray crystal structure of one of them 418 (R=Ph) has been obtained.…”

Section: Camphanes and Isocamphanesmentioning

confidence: 99%

Monoterpenoids

Grayson¹

1998

Nat. Prod. Rep.

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Species Principal constituents ReferenceAbies balsamea Mill -and -pinene, -phellandrene, limonene Achillea biebersteinii Afan piperitone, or cineol and camphor Aloysia triphylla (L'Herit.) Britton citral, limonene Alpinia conchigera Griff. cineol Alseuosmia macrophylla A. Cunn. flowers: linalool Ambrosia microcephala DC. camphor, bornyl acetate Amomum subulatum Roxb. cineol, -terpineol, -and -pinene Artemisia afra yomogi alcohol, artemisyl acetate Artemisia afra Willd. cineol, terpinen-4-ol, borneol Artemisia ordosica -and -pinene, sabinene Austromyrtus dulcis (C. T. White) L. S. Smith (chemotype) -pinene, cineol Boronia megastigma Nees. -ionone, 8-hydroxylinalyl esters, geranyloxy cinnamate Bouea macrophylla Griff. ( E)--ocimene, -pinene Calamintha cretica piperitenone, piperitenone oxide Calamintha incana (Sm.) Boiss. piperitenone oxide Callistemon speciosus Anthor. cineol, -pinene, -terpineol Canella winteriana Gaertn. stem and bark: cineol, terpinen-4-ol, -terpinyl acetate, -terpineol; leaves: myrcene Cedronella canariensis Webb et Berth. ssp. canariensis pinocarvone Chamelaucium uncinatum genotypes -pinene, citronellal, limonene, linalool, -terpinyl acetate Chenopodium ambrosioides limonene, trans-pinocarveol Chenopodium botrys -8 Chrysanthemum balsamata carvone, camphor Chrysanthemum lavandulaefolium menthol Cinnamomum camphora Nees et Ebermaier camphor, cineol, terpinen-4-ol, limonene Cinnamomum puciflorum -2 Citrus grandis limonene Clausena anisata (Willd.) J. D. Hook limonene, myrcene Coleus aromaticus carvacrol, camphor Coreopsis barteri Oliv. & Hiern limonene, -phellandrene Coreopsis grandis Hogg ex Sweet myrcene Coriandrum sativum seeds: linalool Coridothymus capitatus Reich. f. carvacrol 98, 99 Cunila fasiculata menthofuran Cunila microcephala menthofuran, limonene Curcuma aeruginosa Roxb. cineol, camphor Curcuma amada Roxb. myrcene Curcuma aromatica Salisb. cineol, camphor, isoborneol, camphene Curcuma cochinchinensis Gagnep. cineol Curcuma domestica -phellandrene, cineol, p-cymene, -pinene Curcuma pierreana Gagnep. Rhizome, stem: isoborneol, isobornyl acetate leaf: isoborneol, camphor Croton aubrevillei J. Leonard linalool Croton zambesicus Muell. Arg. linalool Cyclotrichum origanifolium (Labill.) Manden. et Scheng. cis-isopulegone, pulegone, isomenthone, menthol Cymbopogon caesius (Nees et Hook. et Arn.) Stapf. perillyl alcohol, geraniol, limonene Cymbopogon citratus (DC.) Stapf. citral, geraniol, myrcene, -and -pinene Cymbopogon khasianus (Munro ex Hack.) Bor. geraniol, geranyl acetate, linalool Cymbopogon schoenanthus piperitone, limonene Daphne mezereum flowers: linalool, linalyl oxides Echinophora chryantha Freyn et Sint. -phellandrene Egletes viscosa various terpenol acetates Elsholtzia ciliata (Thunb.) Hyland chemotype (a): elsholtzia ketone, -thujone chemotype (b): neral, geranial, limonene

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