Tag: M.W=150-200

Sugimori, Akira; Tobita, Etsuo; Kumagai, Yasuyuki; Sato, Gen P. published the artcile< Multiple paths for photo-alkylation and -alkoxylation of 3-pyridinecarboxylic ester in alcohol. Simultaneous contribution of several kinds of excited states>, Electric Literature of 33402-75-4, the main research area is photochem alkylation alkoxylation pyridinecarboxylate.

UV irradiation of Me 3-pyridinecarboxylate (I) in acidic alc. solutions causes alkoxylation and alkylation at the pyridine ring. Photoalkylation occurs via several paths: 1) initiated by the triplet π-π* state; 2) initiated by the triplet n-π* state of the carbonyl moiety of the ester group; 3) initiated by an exciplex between a free-base form of I and a pyridinium form of I; and 4) promoted by Cl- ions. Photoalkoxylation originates from a singlet excited state of I. In the photoreactions of I in strongly acidic MeOH solutions acidified with H2SO4, 3 kinds of excited states (2 kinds of triplet states for alkylation and a singlet state for alkoxylation) contribute simultaneously.

Bulletin of the Chemical Society of Japan published new progress about Photochemical alkylation. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Electric Literature of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sartori, G.; Maggi, R. published the artcile< Carboxylic acid esters: product subclass 16: 3-heteroatom-substituted alkanoic acid esters>, COA of Formula: C6H10O5, the main research area is review heteroatom substituted alkanoic acid ester preparation organic synthesis; beta heteroatom substituted carboxylic acid ester preparation review.

A review of methods to prepare 3-heteroatom-substituted alkanoic acid esters.

Science of Synthesis published new progress about Carboxylic esters Role: SPN (Synthetic Preparation), PREP (Preparation) (β-heteroatom-substituted). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, COA of Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Yang, Jian; Wang, Xin; El-Harairy, Ahmed; Bai, Rongxian; Gu, Yanlong published the artcile< Bronsted acid-catalyzed facile synthesis of α-substituted N-arylaminoacetals and their downstream conversions to functionalized pyrroles>, Synthetic Route of 94-02-0, the main research area is glyoxal dimethyl acetal arylamine ketone Mannich Bronsted acid catalyst; aryl aminoacetal preparation dicarbonyl compound cyclization; pyrrole preparation.

The α-substituted N-arylaminoacetals RNHCH(CH(OCH3)2)CH2C(O)R1 (R = Ph, 3,4-difluorophenyl, 2-chlorophenyl, etc.; R1 = Me, Ph, thiophen-2-yl, etc.) are important building blocks for organic synthesis, which can be synthesized via Mannich reaction by using glyoxal di-Me acetal as a key precursor. As the acetal fragment was known to be susceptible to acid, in literature methods, the Mannich reaction was performed under either neutral or gently acidic conditions. As a result, only a few kinds of α-substituted N-arylaminoacetals have been synthesized via Mannich reaction until now. The Mannich adducts of glyoxal di-Me acetal, arylamines RNH2 and ketones CH3C(O)R1 are quite stable toward strong Bronsted acid. This led to use successfully p-toluenesulfonic acid as the acid catalyst to synthesize a broad range of α-substituted N-arylaminoacetals. The Mannich adducts could be obtained in good to excellent yields. Particularly, these products were demonstrated to be able to react with 1,3-dicarbonyl compounds R2C(O)CH2C(O)R3 [R2 = OCH3, Me, (4-methoxyphenyl)aminyl, etc.; R3 = H, Me, n-Bu, Ph, i-Pr] in the presence of Sc(OTf)3 catalyst. A special class of multi-substituted pyrroles I (R1 = Me, Ph) was thus synthesized and can be converted to some important heterocyclic compounds including Me 2,6-dimethyl-1-(4-methylphenyl)-5-phenyl-1H-indole-3-carboxylate and Me 5-formyl-2-methyl-1-(4-methylphenyl)-1H-pyrrole-3-carboxylate. Di-Me acetals of quinoline-2-carbaldehydes II (R4 = OCH3, H; R5 = H, OCH3; R6 = OCH3; R6R7 = -CH=CH-CH=CH-; R5R6 = -CH=CH-CH=CH-) were also synthesized via one-pot three-component reactions of glyoxal di-Me acetal, electron-rich anilines 3-R4-4-R5-5-R6-6-R7CHNH2 and acetone.

Molecular Catalysis published new progress about 1,3-Dicarbonyl compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 94-02-0 belongs to class esters-buliding-blocks, and the molecular formula is C11H12O3, Synthetic Route of 94-02-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Delayre, Bastien; Piemontesi, Cyril; Wang, Qian; Zhu, Jieping published the artcile< TiCl3-Mediated Synthesis of 2,3,3-Trisubstituted Indolenines: Total Synthesis of (+)-1,2-Dehydroaspidospermidine, (+)-Condyfoline, and (-)-Tubifoline>, Reference of 30095-98-8, the main research area is titanium chloride mediated synthesis indolenine; dehydroaspidospermidine total synthesis; condyfoline total synthesis; tubifoline total synthesis; 1,2-rearrangements; indole alkaloids; natural products; titanium trichloride; total synthesis.

2,3,3-Trisubstituted indolenine constitutes an integral part of many biol. important monoterpene indole alkaloids. We report herein an unprecedented access to this skeleton by a TiCl3-mediated reductive cyclization of tetrasubstituted alkenes bearing a 2-nitrophenyl substituent. The proof of concept is demonstrated firstly by accomplishing a concise total synthesis of (+)-1,2-dehydroaspidospermidine (I) featuring a late-stage application of this key transformation. A sequence of reduction of nitroarene to nitrosoarene followed by 6π-electron-5-atom electrocyclization and a 1,2-alkyl shift of the resulting nitrone intermediate was proposed to account for the reaction outcome. A subsequent total synthesis of (+)-condyfoline (II) not only illustrates the generality of the reaction, but also provides a mechanistic insight into the nature of the 1,2-alkyl shift. The exclusive formation of (+)-condyfoline indicates that the 1,2-alkyl migration follows a concerted Wagner-Meerwein pathway, rather than a stepwise retro-Mannich/Mannich reaction sequence. Conditions for almost quant. conversion of (+)-condyfoline to (-)-tubifoline (III) by way of a retro-Mannich/1,3-prototropy/transannular cyclization cascade are also documented.

Angewandte Chemie, International Edition published new progress about Biomimetic synthesis. 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Reference of 30095-98-8.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Guo, Yinping; Mao, Xin; Xiong, Liang; Xia, Anjie; You, Jing; Lin, Guifeng; Wu, Chengyong; Huang, Luyi; Wang, Yiwei; Yang, Shengyong published the artcile< Structure-Guided Discovery of a Potent and Selective Cell-Active Inhibitor of SETDB1 Tudor Domain>, Synthetic Route of 252932-48-2, the main research area is cell active SETDB1 tudor domain inhibitor structure guided discovery; SETDB1; epigenetics; structure-based optimization; tool compound; tudor domain.

SET domain bifurcated protein 1 (SETDB1) is a histone lysine methyltransferase that promotes the silencing of some tumor suppressor genes and is overexpressed in many cancers. SETDB1 contains a unique tandem tudor domain (TTD) that recognizes histone H3 sequences containing both methylated and acetylated lysines. Beginning with the identification of a hit compound (Cpd1, I), we discovered the first potent and selective small mol. SETDB1-TTD inhibitor (R,R)-59 (II) through stepwise structure-guided optimization. (R,R)-59 showed a KD value of 0.088±0.045μM in the ITC assay. The high potency of (R,R)-59 was well explained by the cocrystal structure of the (R,R)-59-TTD complex. (R,R)-59 is an endogenous binder competitive inhibitor. Evidence has also demonstrated its cellular target engagement. Interestingly, the enantiomer (S,S)-59 did not show activity in all the assays, highlighting the potential of (R,R)-59 as a tool compound in exploring the biol. functions of SETDB1-TTD.

Angewandte Chemie, International Edition published new progress about Antitumor agents. 252932-48-2 belongs to class esters-buliding-blocks, and the molecular formula is C7H10N2O2, Synthetic Route of 252932-48-2.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Prasanth, C. P.; Joseph, Ebbin; Abhijith, A.; Nair, D. S.; Ibnusaud, Ibrahim; Raskatov, Jevgenij; Singaram, Bakthan published the artcile< Stabilization of NaBH4 in Methanol Using a Catalytic Amount of NaOMe. Reduction of Esters and Lactones at Room Temperature without Solvent-Induced Loss of Hydride>, COA of Formula: C6H10O5, the main research area is sodium borohydride methanol catalysis reduction ester lactone.

Rapid reaction of NaBH4 with MeOH precludes its use as a solvent for large-scale ester reductions We have now learned that a catalytic amount of NaOMe (5 mol %) stabilizes NaBH4 solutions in methanol at 25 °C and permits the use of these solutions for the reduction of esters to alcs. The generality of this reduction method was demonstrated using 22 esters including esters of naturally occurring chiral γ-butyrolactone containing dicarboxylic acids. This method permits the chemoselective reductions of esters in the presence of cyano and nitro groups and the reductive cyclization of a pyrrolidinedione ester to a fused five-membered furo[2,3-b]pyrrole and a (-)-crispine A analog in high optical and chem. yields. Lactones, aliphatic esters, aromatic esters containing electron-withdrawing groups, and heteroaryl esters are reduced more rapidly than aryl esters containing electron-donating groups. The 11B NMR spectrum of the NaOMe-stabilized NaBH4 solutions showed a minor quartet due to monomethoxyborohydride (NaBH3OMe) that persisted up to 18 h at 25 °C. We postulate that NaBH3OMe is probably the active reducing agent. In support of this hypothesis, the activation barrier for hydride transfer from BH3(OMe)- onto benzoic acid Me ester was calculated as 18.3 kcal/mol.

Journal of Organic Chemistry published new progress about Aliphatic esters Role: RCT (Reactant), RACT (Reactant or Reagent). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, COA of Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Gualtierotti, Jean-Baptiste; Pasche, Delphine; Wang, Qian; Zhu, Jieping published the artcile< Phosphoric acid catalyzed desymmetrization of bicyclic bislactones bearing an all-carbon stereogenic center: Total syntheses of (-)-rhazinilam and (-)-leucomidine B>, HPLC of Formula: 30095-98-8, the main research area is bicyclic bislactone alc desymmetrization ring opening phosphate catalyst; rhazinilam asym total synthesis; leucomidine B asym total synthesis; alkaloids; natural products; organocatalysis; synthetic methods; total synthesis.

In the presence of a catalytic amount of an imidodiphosphoric acid, enantioselective desymmetrization of bicyclic bislactones by reaction with alcs. took place smoothly to afford enantiomerically enriched monoacids having an all-C stereogenic center. Concise catalytic enantioselective syntheses of both (-)-rhazinilam and (-)-leucomidine B were subsequently developed using Me (S)-4-ethyl-4-formylpimelate monoacid as a common starting material.

Angewandte Chemie, International Edition published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, HPLC of Formula: 30095-98-8.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

White, James D.; Lincoln, Christopher M.; Yang, Jongtae; Martin, William H. C.; Chan, David B. published the artcile< Total Synthesis of Solandelactones A, B, E, and F Exploiting a Tandem Petasis-Claisen Lactonization Strategy>, Application In Synthesis of 617-55-0, the main research area is solandelactone A B E F total synthesis; Petasis Claisen lactonization tandem total synthesis solandelactone; Nozaki Hiyama Kishi coupling total synthesis solandelactone; Simmons Smith cyclopropanation total synthesis solandelactone; methylenation Petasis total synthesis solandelactone.

Solandelactones A, B, E, and F I (R = α-OH, R1 = H; R = β-OH, R1 = H; R = α-OH, R12 = bond; R = β-OH, R12 = bond, resp.) were synthesized using Nozaki-Hiyama-Kishi coupling of iododiene (3S,1E,5Z)-ICH:CHCH(OH)CH2CH:CH(CH2)4Me with aldehydes II obtained by oxidation of the corresponding alcs. Key steps in the synthesis of the latter alcs. (i) a Nagao asym. acetate aldol reaction of aldehyde (E)-Me3CPh2SiOCH2CH:CHCHO with thionothiazolidine III to set in place an alc. that becomes the (7S) lactone center of solandelactones, (ii) a Simmons-Smith cyclopropanation of (3R,4E)-Me3CPh2SiOCH2CH:CHCH(OH)CH2CON(MeO)Me directed by this alc., and (iii) Petasis methylenation of cyclic carbonate IV in tandem with a Claisen rearrangement that generates the octenalactone portion of solandelactones. Synthesis of solandelactones A, B, E, and F confirmed their gross structure and absolute configuration at C7, 8, 10, and 14 but showed that alc. configuration at C11 must be reversed in pairs, A/B and E/F, from the previous assignment made to these hydroid metabolites. A biogenesis of solandelactones is proposed for these C22 oxylipins that parallels a hypothesis put forward previously to explain the origin of C20 cyclopropane-containing algal products.

Journal of Organic Chemistry published new progress about Aldol addition, stereoselective (Nagao). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Application In Synthesis of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Rachedi, Khadidja Otmane; Ouk, Tan-Sothea; Bahadi, Rania; Bouzina, Abdeslem; Djouad, Seif-Eddine; Bechlem, Khaoula; Zerrouki, Rachida; Ben Hadda, Taibi; Almalki, Faisal; Berredjem, Malika published the artcile< Synthesis, DFT and POM analyses of cytotoxicity activity of α-amidophosphonates derivatives: Identification of potential antiviral O,O-pharmacophore site>, Reference of 2743-40-0, the main research area is acylaminoester preparation phosphorylation ethylphosphite; amidophosphonate preparation anticancer agent optimized geometry DFT; amino acid acylation phosphorylation reaction.

The authors studied the cytotoxic activity of three compounds prepared starting from amino acids. These derivatives were evaluated for their in vitro antitumor activity against human cell lines (PRI, K562 and JURKAT). Their cytotoxicity was also evaluated at different concentrations on several cell lines. However, DFT calculation was used to analyze the electronic and geometric characteristics. The HOMO, LUMO and gap energies were also deduced for the stable structure for each compound These results will be correlated with the exptl. values. The bioinformatic POM (Petra/Osiris/Molinspiration) analyses of the relative cytotoxicity of these derivatives are reported in comparison to Chlorambucil.

Journal of Molecular Structure published new progress about Amino acids Role: RCT (Reactant), RACT (Reactant or Reagent). 2743-40-0 belongs to class esters-buliding-blocks, and the molecular formula is C8H18ClNO2, Reference of 2743-40-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Manna, Kartic; Ganguly, Tanusree; Baitalik, Sujoy; Jana, Ranjan published the artcile< Visible-Light- and PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature>, Electric Literature of 30095-98-8, the main research area is secondary amine photochem preparation triphenylphosphine mediator; nitroarene boronic acid intermol reductive amination.

Herein a metal-free, visible-light- and triphenylphosphine-mediated intermol., reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst is presented. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.

Organic Letters published new progress about Amination catalysts (photochem). 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Electric Literature of 30095-98-8.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics