A New Series of Testosterone Esters

Mooradian, A.; Cavallito, Chester J.; Bergman, Arieh; Lawson, Elmer J.; Suter, C. M.

doi:10.1021/ja01178a030

Cited by 58 publications

(41 citation statements)

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“…These compounds were conveniently prepared in 60-80% yield from the condensation of 3,4-dimethoxyphenethylamine with the appropriate aldehyde or ketone followed by reaction of the resulting imine with ethylthioacetyl chloride 28 .Treatment of 50 with 2 equiv of p-TsOH in refluxing benzene afforded 51 in 78% yield (Scheme 10). It is important to note that only one of several possible diastereomers of the fused isoquinoline lactam 51 was observed under the reaction conditions as indicated by 1 H and 13 C-NMR spectral data.…”

Section: Methodsmentioning

confidence: 99%

Application of the tandem thionium/N-acyliminium ion cascade toward heterocyclic synthesis

Padwa¹,

Danca²,

Ginn³

et al. 2001

J. Braz. Chem. Soc.

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Section: Methodsmentioning

confidence: 99%

Application of the tandem thionium/N-acyliminium ion cascade toward heterocyclic synthesis

Padwa¹,

Danca²,

Ginn³

et al. 2001

J. Braz. Chem. Soc.

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“…808/3.01 mbar. IR: 2966IR: , 2929IR: , 2873IR: , 2228IR: , 2161IR: , 2066IR: , 1702IR: , 1455IR: , 1380IR: , 1321IR: , 1247IR: , 1230IR: , 1172IR: , 1162IR: , 1123IR: , 1050IR: , 1031IR: , 1001 IR: 3055, 3014, 2960IR: 3055, 3014, , 2920IR: 3055, 3014, , 2878IR: 3055, 3014, , 2856IR: 3055, 3014, , 2222IR: 3055, 3014, , 2157IR: 3055, 3014, , 2073IR: 3055, 3014, , 1492IR: 3055, 3014, , 1457IR: 3055, 3014, , 1380IR: 3055, 3014, , 1346IR: 3055, 3014, , 1204IR: 3055, 3014, , 1172IR: 3055, 3014, , 1147IR: 3055, 3014, , 1122IR: 3055, 3014, , 1085IR: 3055, 3014, , 1056IR: 3055, 3014, , 1040IR: 3055, 3014, , 1025 (27), 41 (28). 3,6-trimethylcyclohexanecarbaldehyde (7).…”

Section: Experimental Partunclassified

Synthesis of Deuterium‐Labeled Perfume Ingredients as Internal Standards for Their GC/MS Quantification

Chapuis

Cantatore

Fankhauser

et al. 2009

Helvetica Chimica Acta

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The synthesis of various D-labeled perfume ingredients (orris-like, sandalwood-like, musky, and amber-like) is presented. These substances, possessing practically identical H 2 O/solid and solid/gas partition coefficients as their unlabeled analogues, are used as internal standards for the validation of a new analytical GC/MS method for the determination of low residual concentrations in H 2 O after biodegradability tests.

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“…To a solution of N,O-dimethylhydroxylamine hydrochloride (2.00 g, 20.70 mmol) and pyridine (3.30 ml, 41.16 mmol) in 15.0 mL acetonitrile, at 273 K, a solution of 2-(4¢-chlorophenylthio)propanoyl chloride [1] (4.84 g, 20.58 mmol) in 5 mL acetonitrile was added slowly. The reaction mixture was allowed to reach room temperature and was stirred overnight.…”

Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of N-phenyl-3-[2-(4'-chlorophenylthio)propanoyl]-2- azetidinone, C18H16ClNO2S

Zukerman-Schpector

Domingues

Olivato

et al. 2006

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialTo a solution of N,O-dimethylhydroxylamine hydrochloride (2.00 g, 20.70 mmol) and pyridine (3.30 ml, 41.16 mmol) in 15.0 mL acetonitrile, at 273 K, a solution of 2-(4¢-chlorophenylthio)propanoyl chloride [1] (4.84 g, 20.58 mmol) in 5 mL acetonitrile was added slowly. The reaction mixture was allowed to reach room temperature and was stirred overnight. Then it was concentrated and poured into 0.2 N HCl (10.0 mL) solution, washed with water and three times extracted with chloroform. The combined extracts were dried over MgSO 4. After solvent evaporation the crude material was purified by chromatography on silica gel (chloroform), giving a viscous liquid of 2-(4¢-chlorophenylthio)-N-methoxy-Nmethylpropanamide ( 3.93 g, 14.40 mmol, 70 % yield). A solution of n-butyllithium (3.00 mL, 1.9 M in n-hexane) was added to isopropylamine (0.80 mL, 5.47 mmol) in THF (6.6 mL) at 195 K. It was then added a solution of N-phenyl-2-azetidinone (0.80 g, 5.47 mmol) in THF (4.6 mL) and stirred for 30 minutes at the same temperature. Then, a solution of 1.19 g (4.56 mmol) of 2-(4¢-chlorophenylthio)-N-methoxy-N-methylpropanamide in THF (2.0 mL) was added slowly. The reaction was monitored by TLC with chloroform/n-hexane (70 : 30) as eluent. The reaction mixture was poured into aqueous NH 4 Cl and extracted with chloroform (3×). The combined extracts were dried over MgSO 4. After solvent evaporation, the obtained amorphous white solid was recrystallized from methanol giving 1.30 g of the C1(R)C3(S)/C1(S)C3(R) diastereomer of the title compound (2.05 mmol, yield 45 %; m.p. 384-386 K). Crystals for X-ray analysis were obtained by vapor diffusion from chloroform/n-hexane at 278 K. Elemental analysis: found C, 62.73 %; H, 4.88 %; N, 4.37 %; calc. for C 18H16ClNO2S C, 62.51 %; H, 4.66 %; N, 4.05 %. Experimental detailsDue to the poor diffraction quality of the crystal, the number of observed reflections was low. H atoms were geometrically fixed to their parent ones and their displacement parameters calculated as 1.2U eq(C) or 1.5Ueq(C). DiscussionThe four-membered ring is planar within experimental accuracy (r.m.s. being 0.006 Å) and makes a dihedral angle of 6.6(3)°with the phenyl ring attached to it, which can be ascribed to the short C···O interaction: d(C14···O2) = 3.114 (

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A New Series of Testosterone Esters

Cited by 58 publications

References 0 publications

Application of the tandem thionium/N-acyliminium ion cascade toward heterocyclic synthesis

Application of the tandem thionium/N-acyliminium ion cascade toward heterocyclic synthesis

Synthesis of Deuterium‐Labeled Perfume Ingredients as Internal Standards for Their GC/MS Quantification

Crystal structure of N-phenyl-3-[2-(4'-chlorophenylthio)propanoyl]-2- azetidinone, C18H16ClNO2S

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