16240-42-9

Upstream product

• 693-89-0 1-methylcyclopent-1-ene 
• 98486-09-0 (+/-)-2t-chloro-1-methyl-cyclopentan-r-ol 
• 60-29-7 diethyl ether 
• 628-92-2 Cycloheptene 

Downstream Products

• 765-70-8 3-methyl-1,2-cyclopentanedione 
• 101704-30-7 (1RS,2RS)-1-methyl-2-phenylthiocyclopentanol 
• 693-89-0 1-methylcyclopent-1-ene 
• 69429-55-6 2-Fluoro-2-methyl-cyclopentanol 
• 1120-72-5 2-Methylcyclopentanone 
• 765-47-9 1,2-dimethylcyclopentene 
• 19550-45-9 1,2-Dimethylcyclopentan-1-ol 
• 1430230-83-3 2-chloro-4-[[(1R,2R)-2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile 
• 1430230-84-4 2-chloro-4-[[2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile 

Relevant academic research and scientific papers

2-Chloro-4-[[(1R,2R)-2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrile: A Transdermal Selective Androgen Receptor Modulator (SARM) for Muscle Atrophy

A transdermal SARM has a potential to have therapeutic benefit through anabolic activity in muscle while sparing undesired effects of benign prostate hyperplasia (BPH) and liver-mediated decrease in HDL-C. 2-Chloro-4-[(2-hydroxy-2-methyl-cyclopentyl)amino

Developing a multistep continuous manufacturing process for (1R,2R)-2-amino-1-methylcyclopentan-1-ol

A multistep continuous manufacturing process to synthesize (1R,2R)-2-amino-1-methylcyclopentan-1-ol (2) was developed. The step 1/2 flow process mitigated the safety hazard associated with high exothermicity during epoxidation, the epoxide-opening reaction, and the low onset of the epoxide intermediate. Process improvements included a hybrid plug flow reactor (PFR)/continuous stirred tank reactor (CSTR) reaction and a continuous quench/work-up process in step 1; a continuous reaction, extraction, washing, and thin-film distillation work-up in step 2; and a continuous trickle bed hydrogenation in step 3, which provided the desired product with high purity and high ee. The end-to-end continuous process provided significant advantages of cost-saving, minimization of manufacturing space and utilities, and reduction of the cycle time.

Synthesis of chiral hydroxylated cyclopentanones and cyclopentanes

A method for the synthesis of enantiomeric 1,3-dihydroxy and 2,3-dihydroxy cyclopentanones, starting from a commercially available 3-methyl-cyclopentane-1,2-dione 1, is described. Dione 1 was subjected to asymmetric 3-hydroxylation to afford 3-methyl-3-hydroxy-1,2-dione 2. The carbonyl groups in 2 were selectively differentiated by converting them either in dimethylacetal 5 or acetonide 6. Stereoselective reduction of those acetals by using NaBH4 afforded chiral methyl 1,2-dihydroxy cyclopentanone 9 and 1,3-dihydroxy cyclopentanone 10, respectively. The diols obtained were further converted to the corresponding diastereomeric triols 11-13 by hydride reduction.

Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel

Formation of β-Ga2O3nanorings from metal-organic frameworks and their high catalytic activity for epoxidation of alkenes

Here we report a novel synthesis of hollow high-quality β-Ga2O3 nanorings based on an interesting structural evolution from concave Ga-MOF nanodisks. The concave low-crystallinity nanodisks were constructed by non-classical crystallization with particle a

Method for epoxidizing small-molecular olefin

The invention relates to a micromolecular olefin epoxidation method, which is characterized by comprising the following steps: contacting micromolecular olefin, an organic peroxide and a titanium-silicon composite oxide under epoxidation reaction conditions of at least two reaction temperatures of A and B to obtain an alkylene oxide-containing product, wherein the A is 80-95 DEG C, the B is 100-120 DEG C, the titanium-silicon composite oxide is of an amorphous structure, is formed by aggregation of nano-particles and has mesopores in the range of 16-50 nm, the ratio of the volume of the mesopores to the total pore volume is larger than or equal to 80%, and the volume of the mesopores is larger than or equal to 0.5 cm/g. According to the method, the amorphous titanium-silicon-titanium-silicon composite oxide is taken as the catalyst, and at least two sections of conditions with different reaction temperatures are combined, so that compared with the prior art, the catalyst is stable in structure, low in cost, high in olefin epoxidation reaction activity and good in product selectivity.

SELECTIVE ANDROGEN RECEPTOR MODULATORS

The present invention provides novel selective androgen receptor modulators and their salts and pharmaceutical compositions thereof.

Epoxidation of alkenes and their derivatives over Ti-YNU-1

The catalytic properties of Ti-YNU-1 for the epoxidation of various alkenes and their derivatives have been investigated in detail, and further were made a comparison with those of Ti-Beta. The much higher efficiency of Ti-YNU-1 than Ti-Beta was observed in catalyzing the epoxidation of alkenes and their electron-rich analogues. Although it was less active in the epoxidation of α,β-unsaturated ketones, it showed much higher stability. In contrast, Ti leaching from the framework sites occurred to Ti-Beta, and the leaching degree increased with the carbon number of ketones. It was also shown that the catalytic conditions, including the Ti content in samples, H 2O2/substrate ratio, reaction temperature and time, acid washing and catalyst amount, significantly influenced the activity, selectivity and H2O2 efficiency. Co-oxidation of different alkenes led to the activity and epoxide selectivity being different from those obtained in the oxidation of single olefin as a result of the differences in adsorption properties of substrates over various titanosilicates, which affected the diffusion of substrate molecules and accounted for the unique shape-selectivity of Ti-YNU-1.

Effect of a trimethylsilyl moiety on the nucleophilic character of the C=C bond: A comparative kinetic investigation of the epoxidation of substituted and unsubstituted cycloalkenes

The rates of epoxidation of twelve cycloalkenes (6-17) with MCPBA were determined at four temperatures (298, 303, 308 and 313 K). All of them were found to follow second-order kinetics. The silylated cycloalkenes (10-13) react faster than the corresponding unsubstituted cycloalkenes (6-9), but slower than the corresponding methyl cycloalkenes (14-17). Thus, for epoxidation, the silyl moiety is a deactivating group relative to an alkyl group, while it is activating in comparison with hydrogen. When the homologous series 6-9, 10-13 and 14-17 are considered, the order of the rates of epoxidation in each series seems to follow the order of strain energy of its members, i.e., the rate decreases in the sequence: 5-membered > 8-membered > 7-membered > 6-membered. The rate data obtained at four temperatures were employed to calculate ΔH?, ΔS? and ΔG?, based on which a common reaction mechanism is proposed.

Influence of strain on chemical reactivity. Relative reactivity of torsionally distorted double bonds in MCPBA epoxidations

The second-order reaction rates were measured for the MCPBA epoxidation in CH2Cl2 for a series of cyclic olefins including bridgehead olefms and trans-cycloalkenes. As expected, strained bridgehead alkenes and trans-cycloalkenes showed faster reaction rates than nonstrained cis-cycloalkenes. The MM-2 steric energies of alkenes, alkanes, and their corresponding epoxides were calculated to evaluate the strain energy released in each reaction (ΔSE). Plots of log krel vs olefin strain did not show a good correlation. However, the plot of log krel vs ΔSE (which is defined as the steric energy difference between olefin and the corresponding epoxide) showed a good correlation for each set of di- and trisubstituted olefins. This result suggests that ΔSE directly reflects strain energy relief in the transition state. From the slope for the plot log krel vs ΔSE, it was thought that approximately 42% of strain (ΔSE) was released in the transition state for the MCPBA epoxidation. Also, trialkyl-subtituted alkenes were found to be about 50 times more reactive than dialkyl-substituted alkenes in cases where the strain energy relief (ΔSE) is the same. The reaction rate is also plotted versus ionization potential of the olefin, assuming that the major orbital interaction lies between the LUMO of the peracid and the HOMO of the olefin. Although, in some cases, a rough correlation of the reaction rate with the ionization potential of the olefin exists, the frontier orbital interaction is not viewed as the dominant factor since conjugated alkenes, which have higher HOMO energies than simple olefins, are not more reactive in MCPBA epoxidation.