cas 4410-99-5, 2-Phenylethanethiol | Articles data

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The benzyl can be selectively removed by visible light or near visible light. Method for protecting allyl and propargyl group
The invention provides a method for selectively removing benzyl, allyl and propargyl protecting groups by visible light or near visible light, namely a substrate containing benzyl, allyl or propargyl protecting groups. The method has the advantages of simple operation, safe and clean visible light or near visible light as excitation conditions, cheap and easily available reagents, high reaction yield, high reaction chemistry and regional selectivity, and is suitable for selective removal of benzyl, allyl and propargyl protecting groups in various substrates.
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Paragraph 0032

(2021/10/16)

Spontaneous substitution of azulene-derived benzylic alcohols by thiols and its application to labeling/protection of biothiols
By mixing guaiazulene-3-methanol derivatives and thiols at room temperature, benzylic substitution of the alcohol proceeded to yield the corresponding sulfide. Because of the blue color of the guaiazulene derivative, this spontaneous reaction was used for labeling of paper-immobilized biothiols. By treatment with tris(2-carboxyethyl)phosphine hydrochloride, the guaiazulene-3-ylmethyl part of the sulfide could be removed and the original thiol recovered. Based on these findings, a guaiazulene-3-methanol derivative was used as a protective group for the synthesis of cysteine derivatives.
Jin, Yu,Akagawa, Kengo,Kudo, Kazuaki
supporting information

(2021/02/27)

Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols
In this paper we report an efficient and mild procedure for the conversion of organic thiocyanates to thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. The method avoids the use of expensive and hazardous transition metals and harsh reducing agents, as required by reported methods, and provides an attractive alternative to the existing methods for the conversion of organic thiocyanates to thiols.
Maurya, Chandra Kant,Mazumder, Avik,Gupta, Pradeep Kumar
supporting information
p. 1184 - 1188
(2017/07/03)

A method for preparing thiol compounds
The invention provides a preparation method of a thiol compound. According to the preparation method, gas-liquid reaction is carried out on sulfuretted hydrogen and an organic compound containing carbon-carbon double bonds in a solid base catalyst and a reaction solvent through Michael addition under the conditions that the temperature is 20-80 DEG C and the pressure is 0.10-0.12MPa, so as to prepare the thiol compound. The preparation method is mild in reaction condition; the adopted solid base catalyst is strong in alkalinity; the alkaline catalysis position has relatively strong steric hindrance, and the applicability is wide; the solid base catalyst is easy to filter and recover, and can be repeatedly used after being activated; the reaction conversion rate and the selectivity are high; the side reaction is reduced; and the atomic economic utilization rate of the reaction is high.
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Paragraph 0052-0053

(2017/05/12)

Two-step three-component process for one-pot synthesis of 8-alkylmercaptocaffeine derivatives
A highly efficient, odourless and two-step three-component process for one-pot synthesis of some 8-alkylmercaptocaffeine derivatives has been described. The catalyst-free three-component reaction of alkyl bromides, thiourea, and 8-bromocaffeine gave 8-alkylmercaptocaffeine products in excellent to quantitative yields. In addition, the impact of parameters on sample reaction is discussed.
Rad, M. N. Soltani,Maghsoudi
p. 70335 - 70342
(2016/08/06)

Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues
In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl)sulfanyl]caffeine (IC50 = 0.223 μM) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl]caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[(phenylethyl)sulfanyl]caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 μM. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl)sulfanyl]caffeine analogues.
Mostert, Samantha,Mentz, Wayne,Petzer, Anél,Bergh, Jacobus J.,Petzer, Jacobus P.
p. 7040 - 7050
(2013/01/15)

Thioacetate deprotection
A method of thioacetate deprotection by providing a compound of the formula R1—S—CO—R2, and reacting the compound with a quaternary ammonium cyanide salt in the presence of a protic solvent in an inert atmosphere to convert the compound to a product of the formula R1—SH. R1 is an organic group in which the bonding to sulfur is through a saturated carbon, and R2 is an aliphatic group.
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Sheet 1/2

(2008/06/13)

A mild and practical deprotection method for benzyl thioethers
A highly effective and mild deprotection method was developed for benzyl thioethers using dibutylmagnesium in the presence of a catalytic amount of titanocene dichloride. This methodology is applicable to both aromatic and aliphatic benzyl thioethers.
Akao, Atsushi,Nonoyama, Nobuaki,Yasuda, Nobuyoshi
p. 5337 - 5340
(2007/10/03)

Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide
A series of thiol-functionalized organic compounds were selected to analyze the scope and efficiency of a new thioacetate deprotection method using catalytic tetrabutylammonium cyanide (TBACN) to effect the transformation of a thioacetate group to a free thiol in the presence of a protic solvent. Particularly attractive are the mild reaction and workup conditions, reduced byproduct formation typically seen using literature methods and yields of greater than 80% for the free aliphatic thiols. This method is effective on aliphatic thiols with trityl, benzyl, p-halo-benzyl, phenethyl, phenoxyethyl, and cyclohexylethyl structural moieties, but it is not effective with thiophenols.
Holmes, Brian T.,Snow, Arthur W.
p. 12339 - 12342
(2007/10/03)

Synthesis of N-glyoxyl prolyl and pipecolyl amides and thioesters and evaluation of their in vitro and in vivo nerve regenerative effects
The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.
Hamilton, Gregory S.,Wu, Yong-Qian,Limburg, David C.,Wilkinson, Douglas E.,Vaal, Mark J.,Li, Jia-He,Thomas, Christine,Huang, Wei,Sauer, Hansjorg,Ross, Douglas T.,Soni, Raj,Chen, Yi,Guo, Hongshi,Howorth, Pamela,Valentine, Heather,Liang, Shi,Spicer, Dawn,Fuller, Mike,Steiner, Joseph P.
p. 3549 - 3557
(2007/10/03)

A general and mild synthesis of thioesters and thiols from halides
The conversion of a wide variety of halides to thioesters by reaction with potassium thiocetate under mild conditions is described, and the generality of the method is demonstrated.
Zheng, Tu-Cai,Burkart, Maureen,Richardson, David E.
p. 603 - 606
(2007/10/03)

Inhibition of human cytomegalovirus protease N(o) with monocyclic β- lactams
Monocyclic β-lactams have been identified as potent and selective inhibitors of the human cytomegalovirus protease (HCMV) N(o). Two series of these inhibitors are described, a peptidyl series of compounds and non- peptidic molecules featuring lower molecular weights. The SAR work that lead to the discovery of these inhibitors, together with their synthesis is also disclosed.
Deziel,Malenfant
p. 1437 - 1442
(2007/10/03)

The reaction of carbon radicals with sulfur. A convenient synthesis of thiols from carboxylic acids
A new synthesis of thiols in high yield utilizing carbon radicals and elemental sulfur is demonstrated. The procedure is applicable to 1°, 2° and 3° carboxylic acids.
Barton, Derek H. R.,Castagnino, Enzo,Jaszberenyi, Joseph Cs.
p. 6057 - 6060
(2007/10/02)

Glycosylsulfenyl and (Glycosylthio)sulfenyl Halides (Halogeno and Halogenothio 1-Thioglycosides, Resp.): Preparation and Reaction with Alkenes
The disulfides 11-17 and 20 were prepared from 7, 9, and 18 via the dithiocarbonates 8, 10, and 19, respectively (Scheme 2).The structure of 11 and of 13 was established by X-ray analysis.Chlorolysis (SO2Cl2) of 11 gave mostly the sulfenyl chloride 24, characterized as the sulfenamide 26, a small amount of 21, characterized as the (glycosylthio)sulfenamide 23, and the glycosyl chloride 27 (Scheme 3).Bromolysis of 11 followed by treatment of the crude with PhNH2 yielded only 28.Chlorolysis of the diglycosyl disulfide 13, however, gave mostly the (glycosylthio)sulfenyl chloride 21 and 27, besides 24.Bromolysis of 13 (-> 22 and traces of 25) followed by treatment with PhNH2 gave an even higher proportion of 23.Similarly, 20 led to 29 and hence to 30.In solution (CH2Cl2) the sulfenyl chloride 24 decomposes faster than the (thio)sulfenyl chloride 21, and both interconvert.Addition of crude 24 to styrene (-78 deg C) yielded the chloro-sulfide 31 and some 37, both in low yields.The product of the addition of 24 to 1-methylcyclohexene was transformed into the triol 32.Silyl ethers of allylic alcohols reacted with 24 only at room temperature, yielding, after desilylation, isomer mixtures 33 and 34, and pure 35.Much higher yields were achieved for the addition of (thio)sulfenyl halides yielding halogeno-disulfides.Good diastereoselectivities were only obtained with 21, its cyclohexylidene-protected analogue, and 22, and this only in the addition to styrene (-> 36, 37, 38), to (E)-disubstituted alkenes (-> 46, 48, 49a,b, 50a,b, 53), and to trisubstituted alkenes (-> 47, 51, 52, 54, 55).Other monosubstituted alkenes (-> 41-45) and (Z)-hex-2-ene (-> 49c,d, 50c,d) reacted with low diastereoselectivities.Where structurally possible, a stereospecific trans-addition was observed: regioselectivity was observed in the addition to mono- and trisubstituted alkenes and to derivatives of allyl alcohols.The absolute configuration of the 2-chloro-disulfides was either established by X-ray analysis (47a) or determined by transforming (LiAlH4) the chloro-disulfides into known thiiranes (Scheme 5).Thus, 37, 48, and the mixtures of 49a/b and 50a/b gave the thiiranes 56, 61, and 64, respectively, in good-to-acceptable yields (Scheme 5).Harsher conditions transformed 56 into the thiols 57 and 58.Similarly, 61 gave 62.The enantiomeric excesses of these thiols were determined by GC analysis of their esters obtained with (-)-camphanoyl chloride.Addition of 21 to trimethylsilane, followed by LiAlH4 reduction and desilylation, gave the known 66 (63percent, e.e. 74percent).The diastereoselectivity of the addition of 21 to trans-disubstituted and trisubstituted alkenes is rationalized by assuming a preferred conformation of the (thio)sulfenyl chloride and destabilizing steric interactions with one of the alkene substituents, . . .
Huerzeler, Marianne,Bernet, Bruno,Vasella, Andrea
p. 557 - 588
(2007/10/02)

Reductions des thio- et dithioacides et de leurs derives par le complexe BH3-Me2S; transformations fonctionnelles des dithioacides au moyen du catecholborane
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Jabre, Imad,Saquet, Monique,Truillier, Andre
p. 756 - 784
(2007/10/02)

A practical, one-step synthesis of primary thiols under mild and neutral conditions using bis(triorganotin) sulfides
Thiols are obtained from primary organic halides and bis(triaryl/alkyltin) sulfides in the presence of fluoride ion in CH3CN/H2O at 20°C. This simple one-step methodology involving fluorodestannylation is carried out under mild and neutral conditions, in sharp contrast to virtually all known methods. Some attempts at utilizing triorganotin and triorganogermanium mercaptans for the same purpose are reported.
Gingras,Harpp
p. 1397 - 1400
(2007/10/02)

Carbanions Derived from 2-Alkylthiobenzothiazoles. A Novel α-Lithiomethyl Mercaptan Synthon for Mercaptomethylation.
2-Methylthiobenzothiazole readily gives a methyl group lithio derivative which reacts cleanly with electrophiles.The products are conveniently converted into the corresponding thiols by BuLi at -78 deg C, and this sequence thus provides a convenient two-step mercaptomethylation procedure for alkyl halides, aldehydes, and ketones.
Katritzky, Alan R.,Aurrecoechea, Jose M.,Vazques de Miguel, Luis M.
p. 769 - 774
(2007/10/02)

FORMATION OF SULPHUR COMPOUNDS DURING THE HYDRODENITROGENATION OF ANILINE, CYCLOHEXYLAMINE, BENZYLAMINE, AND 2-PHENYLETHYLAMINE ON A NICKEL-TUNGSTEN CATALYST IN THE PRESENCE OF HYDROGEN SULPHIDE
Hydrodenitrogenations of aniline, cyclohexylamine, benzylamine, and 2-phenylethylamine were performed on a sulphided nickel-tungsten catalyst at 300 deg C in an autoclave filled with hydrogen in the absence and in the presence of hydrogen sulphide.Due to the presence of hydrogen sulphide the degree of conversion increased from 0.9 to 3,6percent for aniline and from 72 to 99percent for benzylamine, and the fraction of neutral substances increased from 2.4 to 7percent for cyclohexylamine and from 5.0 to 8.9percent for 2-phenylethylamine.The neutral fractions contained cyclohexanethiol, thiobenzamide, 2-phenylethanethiol, and other sulphur compounds giving evidence that the increased degree of conversion of the amines was due to the hydrogen sulphide taking direct part in the chemical reaction.
Cerny, Mirko,Trka, Antonin
p. 2387 - 2392
(2007/10/02)