144222-34-4

Basic information

• Product Name: (R,R)-TsDPEN
• Synonyms: (R,R)-N-(P-TOLUENESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE;(R,R)-N-(2-AMINO-1,2-DIPHENYLETHYL)-P-TOLUENESULFONAMIDE;(R,R)-TSDPEN;(1R,2R)-N-(P-TOLUENESULFONYL)-1,2-DIPHENYL-1,2-ETHANEDIAMINE;(1R,2R)-TSDPEN;(1R,2R)-(-)-N-P-TOSYL-1,2-DIPHENYLETHYLENEDIAMINE;(1R, 2R)-(-)-N-(4-TOLUENE SULFONYL)1,2-DIPHENYL-1,2-ETHANE DIAMINE;(1R,2R)-(-)-N-(4-TOLUENESULFONYL)-1,2-DIPHENYLETHYLENEDIAMINE
• CAS NO: 144222-34-4
• Molecular Formula: C₂₁H₂₂N₂O₂S
• Molecular Weight: 366.48
• Product Categories: chiral;API intermediates;Asymmetric Synthesis;Synthetic Organic Chemistry;Chiral Compound;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;HydrogenationChiral Building Blocks;Organic Building Blocks;Polyamines;organic amine;Chiral Nitrogen;DPEN Series
• Mol File: 144222-34-4.mol

Chemical Properties

• Melting Point: 128-131 °C(lit.)
• Boiling Point: 537.3 °C at 760 mmHg
• Flash Point: 278.8 °C
• Appearance: White to slightly yellow/Crystals or Crystalline Powder
• Density: 1.1440 (rough estimate)
• Vapor Pressure: 1.28E-11mmHg at 25°C
• Refractive Index: -30 ° (C=0.4, CHCl3)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform, Methanol
• PKA: 10.76±0.50(Predicted)
• Water Solubility: insoluble
• CAS DataBase Reference: (R,R)-TsDPEN(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-TsDPEN(144222-34-4)
• EPA Substance Registry System: (R,R)-TsDPEN(144222-34-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 144222-34-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R,R)-TsDPEN is used as a catalyst for the stereoselective preparation of aromatic ketone derivatives and other chiral organic compounds. Its application in this industry is crucial for the synthesis of enantiomerically pure compounds, which are essential in the development of drugs with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
(R,R)-TsDPEN serves as a chiral diamine ligand in cooperative metal-Bronsted acid catalyzed greener reductive amination using hydrogen gas. This application is particularly important in the synthesis of chiral amines, which are key building blocks in the pharmaceutical, agrochemical, and fine chemical industries. The use of (R,R)-TsDPEN in this process allows for more efficient and environmentally friendly production of these valuable compounds.
Used in Asymmetric Reductive Amination:
(R,R)-TsDPEN is employed as a chiral ligand in the metal-Bronsted acid cooperative catalysis for asymmetric reductive amination. This process is vital for the production of enantiomerically enriched amines, which are widely used in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. The use of (R,R)-TsDPEN in this reaction provides a more selective and efficient method for obtaining the desired chiral products.

InChI:InChI=1/C21H22N2O2S/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17/h2-15,20-21,23H,22H2,1H3/p+1/t20-,21-/m1/s1

Upstream product

• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 191592-36-6 (+)-5-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-8-hydroxy-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepin-4-one 
• 1101899-76-6 [1,2-diphenyl-2-(toluene-4-sulfonylamino)-ethyl]-carbamic acid methyl ester 
• 1245809-68-0 N-((1R,2R)-2-(4-(3,5-dimethylcyclohexa-1,4-dienyl)-butylamino)-1,2-diphenylethyl)-4-methylbenzene-sulfonamide 
• 1241389-19-4 C₃₂H₃₆N₄O₆S₂ 
• 851051-44-0 N-[(1R,2R)-2-(3-cyclohexa-1,4-dienylpropylamino)-1,2-diphenylethyl]-4-methylbenzenesulfonamide 
• 851051-41-7 N-(1R,2R)-[2-(3-cyclohexa-1,4-dienyl-propylamino)-1,2-diphenyl-ethyl]-4-methyl-benzene sulphonamide 
• 1245811-44-2 C₁₈H₂₆N₂O₂S 
• 1402063-40-4 (R,R)-N-(1-benzyl-1,2,3-triazole-4-ylmethyl)-N’-4-toluenesulphonyl-1,2-diphenylethylenediamine 
• 1402063-41-5 (R,R)-N-propargyl-N-methyl-N’-4-toluenesulphonyl-1,2-diphenylethylenediamine 
• 1402063-42-6 (R,R)-N-propargyl-N’-4-toluenesulphonyl-N’methyl-1,2-diphenylethylenediamine 
• 1402063-43-7 (R,R)-N-(1-benzyl-1,2,3-triazole-4-ylmethyl)-N-methyl-N’-4-toluenesulphonyl-1,2-diphenylethylenediamine 
• 1402063-44-8 (R,R)-N-(1-benzyl-1,2,3-triazole-4-ylmethyl)-N’-4-toluenesulphonyl-N’-methyl-1,2-diphenylethylenediamine 

Relevant articles and documents

Synthesis of simple enantiopure tetrahydro-β-carbolines and tetrahydroisoquinolines

Enantioselective hydrogenation of the imines 11-13, 27 and 30 with the Ru complex (R,R)-5 led to the tetrahydro-β-carbolines (1S)-14, (1R)-21 and (1S)-22, and the tetrahydroisoquinoline (1S)-31 with ee > 95%. By employing (S,S)-5 the enantiomers are accessible. The imines 11-12 and 27 were obtained by oxidation of racemic 14, 21 and 22 with KMnO4 in > 58% yield.

A four-hydrogenated 1, 8 - naphthyridine apperception composition preparation method and its prepared chiral products

The invention discloses a preparation method of a tetrahydro 1, 8-naphthyridine compound. The preparation method comprises the following steps: under the existence of a chiral catalyst, enabling a compound with the structure shown in the formula (1) (in the description) and hydrogen to be subjected to addition reaction, wherein the chiral catalyst is a coordination compound with the structure shown in the formula (2) (in the description). The invention further provides a chiral product of the tetrahydro 1, 8-naphthyridine compound, prepared through the preparation method. According to the invention, the proper compound with the structure shown in the formula (1) (in the description) is used as a substrate, and the proper coordination compound with the structure shown in the formula (2) (in the description) is used as the chiral catalyst to perform selective hydrogenation reduction on 1, 8-naphthyridine compound with the structure shown in the formula (1) by adopting hydrogen, so that the chiral product of the tetrahydro 1, 8-naphthyridine compound is prepared with low cost. The chiral product of the tetrahydro 1, 8-naphthyridine compound can be used as a biologically active compound and a structural building block of a chiral drug.

O-bicyclic amine compounds as well as preparation method and chiral products thereof

The invention relates to the field of asymmetric synthesis methods, and discloses a preparation method of o-bicyclic amine compounds. The method comprises the step of enabling a compound having a structure as shown in a formula (1) and hydrogen to be subjected to an addition reaction in presence of a chiral catalyst, wherein the chiral catalyst is a complex having a structure as shown in a formula (2). The invention also provides chiral products of the o-bicyclic amine compounds prepared by the method, and the o-bicyclic amine compounds. After the method is adopted, the selective hydrogenation reduction of the compound having the structure as shown in the formula (1) is realized by using the hydrogen, so that octahydrogenated products, i.e., the o-bicyclic amine compounds shown in a formula (4) are produced with low cost. The formula (1), the formula (2) and the formula (4) are described in the description.

A four-hydrogenated 1, 5 - naphthyridine apperception composition preparation method and its prepared chiral products

The invention discloses a method for preparing a tetrahydro-1,5-naphthyridine compound. The method comprises the following steps: carrying out an addition reaction between a compound with the structure shown as a formula (1) and hydrogen in the presence of a chiral catalyst, wherein the chiral catalyst is a coordination complex with a structure shown as a formula (2). The invention also provides a chiral product of the tetrahydro-1,5-naphthyridine compound prepared by the method. The proper compound with the structure shown as the formula (1) is selected as a substrate, the proper coordination complex with the structure shown as the formula (2) is selected as the chiral catalyst, and selective hydrogenation reduction of the 1,5-naphthyridine compound with the structure shown as the formula (1) is realized by adopting hydrogen, so that the chiral product of the tetrahydro-1,5-naphthyridine compound is prepared at low cost. The chiral product of the tetrahydro-1,5-naphthyridine compound prepared by the invention can serve as a structure block of bioactive compounds and chiral drugs.

(1R,2R)-(+)-(1,2)-DPEN-Bonded Sulfonic Acid Resin: A Trifunctional Heterogeneous Catalyst for Asymmetric Michael Additions of Acetone to Nitroolefins

Based on (1R,2R)-(+)-(1,2)-DPEN skeleton, a series of primary amine-sulfamide bifunctional catalysts were synthesized, which exhibited excellent catalytic performance in the Michael addition of acetone to β-nitrostyrene. Therefore, a trifunctional heterogeneous catalyst was designed and prepared by simple N-sulfonyl reaction of (1R,2R)-(+)-(1,2)-DPEN and sulfonyl chloride resin. It was employed for the aforementioned addition without any additive and satisfactory results (80.5% conversion; 84.3% ee) were obtained. Meanwhile, the structural and textural properties of the catalyst were characterized by infrared spectroscopy (FT-IR), elemental analysis, SEM, and N2 adsorption and desorption experiments. Finally, the generality of the catalyst was investigated.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Organocatalytic michael addition of 1,3-dicarbonyl indane compounds to nitrostyrenes

To map out the efficient organocatalyst requirements in the Michael addition of 1,3-dicarbonyl indane compounds to nitrostyrenes, a dozen different amino organocatalysts containing a p-toluenesulfonyl group (Ts) have been evaluated; excellent enantioselectivities (up to er 92:8) were obtained with a primary amine-based Ts-DPEN catalyst and a plausible catalytic reaction mechanism was proposed on the basis of the experimental results. Copyright

Enantioselective Michael addition of ketones to maleimides catalyzed by bifunctional monosulfonyl DPEN salt

An unprecedented enantioselective Michael addition of various ketones to maleimides catalyzed by a simple bifunctional primary amine, monosulfonyl DPEN salt, is reported and provides the desired adducts in good to excellent yields (up to 99%) with excellent enantioselectivities (up to 99%).

Asymmetric de novo synthesis of fluorinated d-glucitol and d-mannitol analogues

A highly efficient anti-SE2′ electrophilic fluorination of enantioenriched allylsilanes a subsequent dihydroxylation of the resulting allylic fluorides were used as key steps for the synthesis of three fluorinated carbohydrate analogues, 1,5-di-O-benzyl-2-deoxy-2-fluoro-d-glucitol, 2,6-di-O-benzyl-5-deoxy-5-fluoro-l-glucitol and 1,5-di-O-benzyl-2-deoxy-2-fluoro-d-mannitol. A new catalytic asymmetric route to 1-benzyloxy-4-trimethylsilyl-but-3-yn-2-ol, a common precursor to two advanced allylsilanes, is also described featuring a Noyori asymmetric transfer hydrogenation reaction.

Vanadium-catalyzed asymmetric epoxidation of allylic alcohols in water

Asymmetric V-catalyzed epoxidation of allylic alcohols can be carried out in water with chiral ligands, which incorporate sulfonamide and hydroxamic acid fragments. Furthermore, the reaction, notorious for its ligand-deceleration effect, in water turned into the ligand-accelerated process. By using this aqueous protocol, a range of allylic alcohols were epoxidized with up to 94% ee.