59812-92-9

Upstream product

• 2437-56-1 1-tridecene 
• 35237-38-8 (+/-)-2-aminotridecenoic acid 
• 96947-50-1 (S)-2-aminotridecanoic acid 
• 405552-38-7 (R)-2-hydroxytridecanoic acid 
• 96883-08-8 (S)-2-hydroxytridecanoic acid 
• 96883-10-2 methyl (R)-2-hydroxytridecanoate 
• 97859-56-8 (S)-1-Phenylsulfanyl-tridecan-2-ol 
• 112-29-8 1-bromo dodecane 
• 17049-50-2 n-decyl magnesium bromide 
• 129752-93-8 Toluene-4-sulfonic acid (S)-2-hydroxy-tridecyl ester 
• 33968-46-6 (S)-1,2-dihydroxytridecane 
• 1713-31-1 (+/-)-1,2-epoxytridecane 
• 129752-93-8 (R)-2-hydroxytridecyl 4-methylbenzenesulfonate 
• 96883-16-8 (R)-1,2-dihydroxytridecane 

Downstream Products

• 10486-19-8 tridecanal 
• 33968-46-6 (S)-1,2-dihydroxytridecane 
• 1713-31-1 (R)-(+)-1,2-epoxytridecane 
• 1713-31-1 (S)-(-)-1,2-epoxytridecane 
• 1653-31-2 (S)-(+)-tridecan-2-ol 
• 120876-13-3 (S)-(+)-1-methyldodecyl acetate 
• 958221-98-2 (S)-3-Hydroxy-tetradecanenitrile 
• 140459-83-2 (R)-2-tridecanyl acetate 
• 35683-15-9 (3S)-3-hydroxytetradecanoic acid 
• 104872-04-0 Orlistat 
• 104871-99-0 (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one 

Relevant academic research and scientific papers

Stereochemistry of Δ4 dehydrogenation catalyzed by an ivy (Hedera helix) Δ9 desaturase homolog

The stereochemistry of palmitoyl-ACP Δ4 desaturase-mediated dehydrogenation has been examined by tracking the fate of deuterium atoms located on stereospecifically monodeuterated substrates-(4S)- and (4R)-[4-2H1]-palmitoyl-ACP and (5S)- and (5R)-[5- 2H1]-palmitoyl-ACP. It was found that the introduction of the (Z)-double bond between C-4 and C-5 of a palmitoyl substrate occurs with pro-R enantioselectivity - a result which matches that obtained for a closely related homolog-castor stearoyl-ACP Δ9 desaturase. These data show that despite the difference in regioselectivity between the two enzymes, the stereochemistry of hydrogen removal is conserved. The Royal Society of Chemistry.

In situ fabricated MOF-cellulose composite as an advanced ROS deactivator-convertor: Fluoroswitchable bi-phasic tweezers for free chlorine detoxification and size-exclusive catalytic insertion of aqueous H2O2

Combining the merits of structural diversity, and purposeful implantation of task-specific functionalities, metal-organic frameworks (MOFs) instigate targeted reactive oxygen species (ROS) scavenging and concurrent detoxification via self-calibrated emission modulation. Then again, grafting of catalytically active sites in MOFs can benefit developing a greener protocol to convert ROS generators to technologically important building blocks, wherein tailorable MOF-composite fabrication is highly sought for practical applications, yet unexplored. The chemo-robust and hydrogen-bonded framework encompassing free -NH2 moiety affixed pores serves as an ultra-fast and highly regenerable fluoro-probe for selective detection of toxic ROS producers hypochlorite ion (ClO-) and H2O2 with record-level nanomolar sensitivity. While the bio-relevant antioxidant l-ascorbic acid (AA) imparts notable quenching to the MOF, a significant 3.5 fold emission enhancement with bi-phasic colorimetric variation ensues when it selectively scavenges ClO- from uni-directional porous channels through an unprecedented molecular tweezer approach. Apart from a battery of experimental evidence, density functional theory (DFT) results validate "on-off-on"fluoroswitching from redistribution of MOF orbital energy levels, and show guest-mediated exclusive transition from "Tight state"to "Loose state". The coordination frustrated metal site engineered pore-wall benefits the dual-functionalized MOF in converting the potential ROS generator H2O2via selective alkene epoxidation under mild-conditions. Importantly, sterically encumbered substrates exhibit poor conversion and demonstrate first-ever pore-fitting-induced size selectivity for this benign oxidation. Judiciously planned control experiments in combination with DFT-optimized intermediates provide proof-of-concept to the ionic route of ROS conversion. Considering an effective way to broaden the advanced applications of this crystalline material, reconfigurable MOF@cotton fiber (CF) is fabricated via in situ growth, which scavenges free chlorine and concomitantly squeezes it upon exposure to AA with obvious colorimetric changes over multiple real-life platforms. Furthermore, multi-cyclic alkene epoxidation by MOF@CF paves the way to futuristic continuous flow reactors that truly serves this smart composite as a bimodal ROS deactivator-convertor and explicitly denotes it as an advanced promising analogue from contemporary state-of-the-art materials.

Proton Switch in the Secondary Coordination Sphere to Control Catalytic Events at the Metal Center: Biomimetic Oxo Transfer Chemistry of Nickel Amidate Complex

High-valent metal-oxo species are key intermediates for the oxygen atom transfer step in the catalytic cycles of many metalloenzymes. While the redox-active metal centers of such enzymes are typically supported by anionic amino acid side chains or porphyrin rings, peptide backbones might function as strong electron-donating ligands to stabilize high oxidation states. To test the feasibility of this idea in synthetic settings, we have prepared a nickel(II) complex of new amido multidentate ligand. The mononuclear nickel complex of this N5 ligand catalyzes epoxidation reactions of a wide range of olefins by using mCPBA as a terminal oxidant. Notably, a remarkably high catalytic efficiency and selectivity were observed for terminal olefin substrates. We found that protonation of the secondary coordination sphere serves as the entry point to the catalytic cycle, in which high-valent nickel species is subsequently formed to carry out oxo-transfer reactions. A conceptually parallel process might allow metalloenzymes to control the catalytic cycle in the primary coordination sphere by using proton switch in the secondary coordination sphere.

Total Synthesis of Tetrahydrolipstatin, Its Derivatives, and Evaluation of Their Ability to Potentiate Multiple Antibiotic Classes against Mycobacterium Species

Tetrahydrolipstatin (THL, 1a) has been shown to inhibit both mammalian and bacterial α/β hydrolases. In the case of bacterial systems, THL is a known inhibitor of several Mycobacterium tuberculosis hydrolases involved in mycomembrane biosynthesis. Herein we report a highly efficient eight-step asymmetric synthesis of THL using a route that allows modification of the THL α-chain substituent to afford compounds 1a through 1e. The key transformation in the synthesis was use of a (TPP)CrCl/Co2(CO)8-catalyzed regioselective and stereospecific carbonylation on an advanced epoxide intermediate to yield a trans-β-lactone. These compounds are modest inhibitors of Ag85A and Ag85C, two α/β hydrolases of M. tuberculosis involved in the biosynthesis of the mycomembrane. Among these compounds, 10d showed the highest inhibitory effect on Ag85A (34 ± 22 μM) and Ag85C (66 ± 8 μM), and its X-ray structure was solved in complex with Ag85C to 2.5 ? resolution. In contrast, compound 1e exhibited the best-in-class MICs of 50 μM (25 μg/mL) and 16 μM (8.4 μg/mL) against M. smegmatis and M. tuberculosis H37Ra, respectively, using a microtiter assay plate. Combination of 1e with 13 well-established antibiotics synergistically enhanced the potency of few of these antibiotics in M. smegmatis and M. tuberculosis H37Ra. Compound 1e applied at concentrations 4-fold lower than its MIC enhanced the MIC of the synergistic antibiotic by 2-256-fold. In addition to observing synergy with first-line drugs, rifamycin and isoniazid, the MIC of vancomycin against M. tuberculosis H37Ra was 65 μg/mL; however, the MIC was lowered to 0.25 μg/mL in the presence of 2.1 μg/mL 1e demonstrating the potential of targeting mycobacterial hydrolases involved in mycomembrane and peptidoglycan biosynthesis.

Dinuclear Iron(III) and Nickel(II) Complexes Containing N-(2-Pyridylmethyl)-N′-(2-hydroxyethyl)ethylenediamine: Catalytic Oxidation and Magnetic Properties

Dinuclear FeIII and NiII complexes, [(phenO)Fe(N3)]2(NO3)2 (1) and [(phenOH)Ni(N3)2]2 (2), were prepared by treating Fe(NO3)3?9 H2O and Ni(NO3)2?6 H2O in methanol, respectively, with phenOH (=N-(2-pyridylmethyl)-N′-(2-hydroxyethyl)ethylenediamine) and NaN3; both 1 and 2 were characterized by elemental analysis, IR spectroscopy, X-ray diffraction, and magnetic susceptibility measurements. Two ethoxo-bridged FeIII and two azido-bridged NiII were observed in 1 and 2, respectively; corresponding antiferromagnetic interaction via the bridged ethoxo groups and strong ferromagnetic coupling via the bridged end-on azido ligands within the dimeric unit were observed. Complex 1 did not exhibit any catalytic activity, while 2 exhibited excellent catalytic activities for the epoxidation of aliphatic, aromatic, and terminal olefins.

Regiocontrolled syntheses of FAHFAs and LC-MS/MS differentiation of regioisomers

An efficient regiospecific total synthesis of several branched fatty acyl hydroxyl-fatty acids (FAHFA) has been achieved from available terminal alkenes and alkynes. The key steps feature a boron trifluoride mediated epoxide ring opening with acetylide carbanions, followed by hydrogenation of the alkyne function. The carboxylic acid of the hydroxylated chains is introduced at the last step of the synthesis to allow the esterification of the branched hydroxyl group by fatty acids beforehand. The chemical syntheses of a "linear" FAHFA and a branched FAHFA analog containing a Z-olefin in the hydroxyl-fatty acid chain are also reported. A LC-MS/MS method has been developed. Several reversed phase columns were compared. Regioisomers were separated.

Trinuclear nickel and cobalt complexes containing unsymmetrical tripodal tetradentate ligands: Syntheses, structural, magnetic, and catalytic properties

The coordination chemistries of the tetradentate N2O2-type ligands N-(2-pyridylmethyl)iminodiethanol (H2pmide) and N-(2-pyridylmethyl)iminodiisopropanol (H2pmidip) have been investigated with nickel(ii) and cobalt(ii/iii) ions. Three novel complexes prepared and characterized are [(Hpmide)2Ni3(CH3COO)4] (1), [(Hpmide)2Co3(CH3COO)4] (2), and [(pmidip)2Co3(CH3COO)4] (3). In 1 and 2, two terminal nickel(ii)/cobalt(ii) units are coordinated to one Hpmide- and two CH3CO2-. The terminal units are each connected to a central nickel(ii)/cobalt(ii) cation through one oxygen atom of Hpmide- and two oxygen atoms of acetate ions, giving rise to nickel(ii) and cobalt(ii) trinuclear complexes, respectively. Trinuclear complexes 1 and 2 are isomorphous. In 3, two terminal cobalt(iii) units are coordinated to pmidip2- and two CH3CO2-. The terminal units are each linked to a central cobalt(ii) cation through two oxygen atoms of pmidip2- and one oxygen atom of a bidentate acetate ion, resulting in a linear trinuclear mixed-valence cobalt complex. 1 shows a weak ferromagnetic interaction with the ethoxo and acetato groups between the nickel(ii) ions (g = 2.24, J = 2.35 cm-1). However, 2 indicates a weak antiferromagnetic coupling with the ethoxo and acetato groups between the cobalt(ii) ions (g = 2.37, J = -0.5 cm-1). Additionally, 3 behaves as a paramagnetic cobalt(ii) monomer, due to the diamagnetic cobalt(iii) ions in the terminal units (g = 2.53, =D= = 36.0 cm-1). No catalytic activity was observed in 1. However, 2 and 3 showed significant catalytic activities toward various olefins with modest to good yields. 3 was slightly less efficient toward olefin epoxidation reaction than 2. Also 2 was used for terminal olefin oxidation reaction and was oxidised to the corresponding epoxides in moderate yields (34-75%) with conversions ranging from 47-100%. The cobalt complexes 2 and 3 promoted the O-O bond cleavage to ～75% heterolysis and ～25% homolysis.

A discrete {Co4(μ3-OH)4}4+ cluster with an oxygen-rich coordination environment as a catalyst for the epoxidation of various olefins

Using the sterically hindered terphenyl-based carboxylate, the tetrameric Co(ii) complex [Co4(μ3-OH)4(μ-O2CAr4F-Ph)2(μ-OTf)2(Py)4] (1) with an asymmetric cubane-type core has been synthesized and fully characterized by X-ray diffraction, UV-vis spectroscopy, and electron paramagnetic resonance spectroscopy. Interestingly, the cubane-type cobalt cluster 1 with 3-chloroperoxybenzoic acid as the oxidant was found to be very effective in the epoxidation of a variety of olefins, including terminal olefins which are more challenging targeting substrates. Moreover, this catalytic system showed a fast reaction rate and high epoxide yields under mild conditions. Based on product analysis and Hammett studies, the use of peroxyphenylacetic acid as a mechanistic probe, H218O-exchange experiments, and EPR studies, it has been proposed that multiple reactive cobalt-oxo species CoVO and CoIVO were involved in the olefin epoxidation.

Synthesis, characterization, crystal structure determination and catalytic activity in epoxidation reaction of two new oxidovanadium(IV) Schiff base complexes

The five coordinated vanadium(IV) Schiff base complexes of VOL1 (1) and VOL2 (2), HL1?=?2-{(E)-[2-bromoethyl)imino]methyl}-2- naphthol, HL2?=?2-{(E)-[2-chloroethyl)imino]methyl}-2- naphthol, have been synthesized and they were characterized by using single-crystal X-ray crystallography, elemental analysis (CHN) and FT-IR spectroscopy. Crystal structure determination of these complexes shows that the Schiff base ligands (L1 and L2) act as bidentate ligands with two phenolato oxygen atoms and two imine nitrogen atoms in the trans geometry. The coordination geometry around the vanadium(IV) is distorted square pyramidal in which vanadium(IV) is coordinated by two nitrogen and two oxygen atoms of two independent ligands in the basal plane and by one oxygen atom in the apical position. The catalytic activity of the Schiff base complexes of 1 and 2 in the epoxidation of alkenes were investigated using different reaction parameters such as solvent effect, oxidant, alkene/oxidant ratio and the catalyst amount. The results showed that in the presence of TBHP as oxidant in 1: 4 and 1:3 ratio of the cyclooctene/oxidant ratio, high epoxide yield was obtained for 1 (76%) and 2 (80%) with TON(= mole of substrate/mole of catalyst) of 27 and 28.5, respectively, in epoxidation of cyclooctene.

Terminal and internal olefin epoxidation with cobalt(II) as the catalyst: Evidence for an active oxidant CoII-acylperoxo species

A simple catalytic system that uses commercially available cobalt(II) perchlorate as the catalyst and 3-chloroperoxybenzoic acid as the oxidant was found to be very effective in the epoxidation of a variety of olefins with high product selectivity under mild experimental conditions. More challenging targets such as terminal aliphatic olefins were also efficiently and selectively oxidized to the corresponding epoxides. This catalytic system features a nearly nonradical-type and highly stereospecific epoxidation of aliphatic olefin, fast conversion, and high yields. Olefin epoxidation by this catalytic system is proposed to involve a new reactive CoII-OOC(O)R species, based on evidence from H218O-exchange experiments, the use of peroxyphenylacetic acid as a mechanistic probe, reactivity and Hammett studies, EPR, and ESI-mass spectrometric investigation. However, the O-O bond of a CoII-acylperoxo intermediate (CoII-OOC(O)R) was found to be cleaved both heterolytically and homolytically if there is no substrate.