Category: 29841-69-8

29841-69-8, (1S,2S)-(-)-1,2-Diphenylethylenediamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Bis-aldehyde c (0.53 g,1.1 mmol) in dry THF (1.2 mL) was taken in a single-necked 50 mL round-bottom flask to which the solution of 1S,2S-(+)-1,2-diaminocyclohexane (0.14 g,1.2 mmol)/1S,2S-(-)-1,2-diphenylethane-1,2-diamine (0.27 g, 1.2 mmol) in dry THF (0.6 mL) was added slowly and the resultant solutions were stirred at room temperature. After completion of the reaction (2 h) checked on TLC, the solvent was removed completely under reduced pressure. The bright yellow solids were extracted with dichloromethane (50 mL), and the organic layer was washed with water (3 ¡Á 50 mL), brine (3 ¡Á 50 mL) and finally dried over anhydrous Na2SO4. After removal of dichloromethane under reduced pressure, the chiral dimeric macrocyclic ligands 3′ and 4′ were purified by silica gel chromatography (100-200 mesh) with a EtOAc-to-Hexane of 3:2.3′: Yield 96%. m.p. 76 C. 1H NMR (500 MHz, CDCl3): delta 1.38 (36H, s),1.67-1.93 (16H, m), 3.32 (4H, m), 3.55 (8H, t, J = 5), 3.61 (16H, t, J = 7), 4.37 (8H, s), 6.97 (4H, s), 7.20 (4H, s), 8.26 (4H, s), 13.86 (4H, br) ppm. 13C NMR (125 MHz, CDCl3): 25.0, 31.0, 34.7, 70.7, 72.2, 74.0, 74.8, 79.0, 119.8, 128.7, 131.2, 138.8, 161.6, 167.0 ppm; FT-IR (KBr): nu 3424, 2934, 2863, 2361, 1628, 1537, 1446, 1384, 1317, 1239, 1098, 940, 868, 785, 671, 563, 420 cm-1. (c = 0.052, CH2Cl2). Anal. Calcd. for C72H104N4O12 C, 71.02; H, 8.61; N, 4.60. Found C, 71.05; H, 8.63; N, 4.62. MALDI-TOF: m/z Calcd. for [C72H104N4O12] 1217.62, Found 1218.19 [M+H].4′: Yield 93%. m.p. 95 C. 1H NMR (200 MHz, CDCl3): delta 1.40 (36H, s), 3.53-3.63 (24H, m), 4.37 (8H, s), 4.71 (4H, s), 6.97 (4H, s), 7.19-7.29 (24H, m), 8.32 (4H, s), 13.78 (4H, br) ppm. 13C NMR (50 MHz, CDCl3): 29.3, 34.8, 69.1, 70.6, 73.1, 80.0, 118.1, 127.6, 128.1, 128.3, 129.8, 137.3, 139.5, 159.9, 166.7 ppm. FT-IR (KBr): nu 3452, 2952, 2865, 2361, 1626, 1446, 1386, 1357, 1320, 1266, 1208, 1100, 1035, 936, 871, 801, 775, 573 cm-1. (c = 0.108, CHCl3). Anal. Calcd. for C88H108N4O12 C, 74.76; H, 7.70; N, 3.96. Found C, 74.75; H, 7.73; N, 3.98. MALDI-TOF: m/z Calcd. for [C88H108N4O12] 1413.82, Found 1414.19 [M+H].

29841-69-8, The synthetic route of 29841-69-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Kureshy, Rukhsana I.; Roy, Tamal; Khan, Noor-Ul H.; Abdi, Sayed H.R.; Sadhukhan, Arghya; Bajaj, Hari C.; Journal of Catalysis; vol. 286; (2012); p. 41 – 50;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29841-69-8,(1S,2S)-(-)-1,2-Diphenylethylenediamine,as a common compound, the synthetic route is as follows.

To a solution of (S,S)-1,2-diphenylethane-1,2-diamine (424 mg,2 mmol) and triethylamine (280 muL, 2 mmol) in CH2Cl2 (10 mL), 4-(bromomethyl)phenylsulfonyl chloride 1 (525 mg, 1.96 mmol) in dichloromethane(10 mL) were added dropwise at 0 C. The reactionmixture was stirred at room temperature for 0.5 h. After removal ofsolvents under reduced pressure, the residue was purified by silica gelcolumn chromatography. The product 3 was obtained as white solid(0.45 g, 60%). 1H NMR (400 MHz, CDCl3) delta 7.46-7.31 (m, 2H),7.27-6.98 (m, 12H), 4.50 (s, 2H), 4.45 (d, J=5.1 Hz, 1H), 4.20 (d,J=5.2 Hz, 1H). 13C NMR (100 MHz, CDCl3) delta 141.5, 140.0, 136.9,129.0, 128.6, 128.3, 128.2, 127.7, 127.5, 127.5, 127.4, 63.0, 60.0,31.7. HRMS (ESI): m/z calculated for C21H21N2O2SBr [M+H]+:445.0580; found: 445.0583., 29841-69-8

29841-69-8 (1S,2S)-(-)-1,2-Diphenylethylenediamine 6931238, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Zheng, Dongsong; Liu, Rui; Wang, Yu; Cheng, Tanyu; Liu, Guohua; Molecular catalysis; vol. 455; (2018); p. 103 – 107;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

29841-69-8, (1S,2S)-(-)-1,2-Diphenylethylenediamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

0.592 g (2.79 mmol) of (S,S)-DPEN (MW: 212.3) was introduced into a 50-mL three-necked flask and subjected to argon-gas replacement. 25 mL of dehydrated methylene chloride and 0.41 mL (2.93 mmol) of triethylamine were added and cooled to 0 C. To this solution, a solution consisting of 0.515 g (2.79 mmol) of isohexyl sulfonyl chloride (MW: 184.68) and 25 mL of dehydrated methylene chloride was slowly added dropwise, and stirred at 0 C. for one night. This solution was washed twice with water, then the solvent in the organic layer was distilled away, and dried under reduced pressure to give 1.656 g of a crude product. The crude product was purified by silica-gel column chromatography (silica gel 60N, n-hexane:AcOEt=1:1, then AcOEt 100%) to give 0.306 g of (S,S)-(C2H5)2CHCH2SO2DPEN (30% yield). 1H NMR (400 MHz, CDCl3, rt, delta/ppm): 0.67 (q, J=7.3 Hz, 6H, (C3CH2)2CH), 1.10-1.38 (m, 4H, (CH3C2)2CH), 1.62-1.76 (m, 1H, (CH3CH2)2C), 2.22 (d, J=6.4 Hz, 2H, C2SO2), 4.29 (d, J=5.5 Hz, 1H, C6H5CNH2), 4.56 (d, J=5.5 Hz, 1H, C6H5CNHSO2), 7.15-7.45 (m, 10H, aromatic proton).

29841-69-8, 29841-69-8 (1S,2S)-(-)-1,2-Diphenylethylenediamine 6931238, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; Kanto Kagaku Kabushiki Kaisha; US2010/261924; (2010); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

29841-69-8, (1S,2S)-(-)-1,2-Diphenylethylenediamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: (1R, 2R)-N-p-styrenesulfonyl-1,2-diphenylethylenediamine was synthesized as follows: 1g of (1R, 2R)-1,2-diphenylethylenediamine (4.71mmol) was dissolved in 20mL of CH2Cl2 in the presence of excessive of triethylamine and cooled to 0C, followed by the slow addition of 5mL of CH2Cl2 solution containing 1g of p-styrenesulfonyl chloride (4.78mmol), and stirred at room temperature overnight. The solution was washed with 5% NaOH aqueous solution, dried with MgSO4, and evaporated under vacuum to remove the solvent. The obtained solid was dissolved in diethyl ether, followed by the addition of 1mL of concentrated HCl (37wt%). The formed white precipitated was filtrated, treated with 5% NaOH aqueous, and then extracted with CH2Cl2 for 3 times. The combined organic phase was washed thoroughly with brine and dried over with MgSO4. The solvent was removed under vacuum and 1.28g of light yellow solid (72% yield) was obtained, which was denoted as V-TsDPEN [11]. 1H NMR (400MHz, DMSO-d6, 298K, TMS): delta6.64-7.38 (m, 14H), 6.64-6.67 (m, 1H), 5.87 (d, 1H, J=16.8Hz), 5.35 (d, 1H, J=11.2Hz), 4.33 (d, 1H, J=7.2Hz), 3.95 (d, 1H, J=6.6Hz) ppm., 29841-69-8

As the paragraph descriping shows that 29841-69-8 is playing an increasingly important role.

Reference£º
Article; Sun, Qi; Jin, Yinying; Zhu, Longfeng; Wang, Liang; Meng, Xiangju; Xiao, Feng-Shou; Nano Today; vol. 8; 4; (2013); p. 342 – 350;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29841-69-8,(1S,2S)-(-)-1,2-Diphenylethylenediamine,as a common compound, the synthetic route is as follows.

Example 4: Preparation of RuCI [ (1 S, 2S)-p-dansylNCH (C6H5) CH (C6H5) NH2] (rl6-p-cymene) a) Preparation of (S, S)-5-dimethylamino-naphthalene-1-sulfonic acid (2-amino-1, 2-diphenyl- ethyl)-amide : To a solution of (S, S)-diphenylethylenediamine (250 mg, 1.2 mmol) and triethylamine (0.5 ml) in THF is added dropwise a solution of dansyl chloride (318 mg, 1.2 mmol) in THF (2 mi) at 0C. After stirring 16 h at RT the solvent is removed in vacuum and the residue is resolved in methylenchloride (20 ml). The organic solution is washed with NaHCO3 solution (5 ml), dried over Na2SO4 and after filtration the solvent is removed. Flash chromatographie afford (S, S)-5-dimethylamino-naphthalene-1-sulfonic acid (2-amino-1,2- diphenyl-ethyl)-amide as yellow oil which crystallizes by drying in vacuum. M: 445. 59. in- NMR (400 MHz, CDCl3) : 8.36 (t, J = 7.5 Hz, 2 H), 8.17 (dd, J = 7.2, 1.2 Hz, 1 H), 7.47 (dd, J = 8.8 Hz, 1 H), 7. 34 (dd, J = 8.5 Hz, 1 H), 7.24-7. 16 (m, 4 H), 7.11 (d, J = 7.5 Hz, 1 H), 6.99- 6.74 (m, 6 H), 4.61 (d, J = 8.5 Hz, 1 H), 4.20 (d, J = 8.5 Hz, 1 H), 2.80 (s, 6 H)

29841-69-8, The synthetic route of 29841-69-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/92294; (2005); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29841-69-8,(1S,2S)-(-)-1,2-Diphenylethylenediamine,as a common compound, the synthetic route is as follows.

trans-RuH(eta1-BH4)[(s)-xylbinap][(S,S)-dpen] was synthesized. First, trans-RuCl2[(S)-xylbinap][(S,S)-dpen] was synthesized. That is, [RuCl2(benzene)]2 (62.5 mg; 0.125 mmol) (made by Aldrich Inc.) and (R)-XylBINAP (183.5 mg; 0.25 mmol) were weighed and placed in a 75 mL Schlenk reaction tube equipped with a stirrer coated with polytetrafluoroethylene, and after depressurizing the interior of the vessel to eliminate air, argon was introduced. After then adding DMF (3 mL) with a syringe, heating in an oil bath set to 100 C. was performed for 10 minutes under an argon atmosphere. After cooling the reaction solution to room temperature, DMF was distilled off under reduced pressure(1 mmHg). (S, S)-DPEN (53.0 mg; 0.25 mmol) (made by Kankyo Kagaku Center Co., Ltd.) and methylene chloride (3 mL) were then added under an argon gas flow to the reddish-brown RuCl2[(S)-xylbinap] (dmf)n solution thus obtained and stirring at 25 C. was performed for 1 hour. A green-colored crude product obtained by distilling off the methylene chloride under reduced pressure (1 mmHg) was dissolved in a 1:1 volume ratio methylene chloride/diethyl ether mixed solvent (2 mL) and this was passed through a column packed with silica gel (5 g) using a 1:1 volume ratio diethyl ether-hexane solution as an eluate to remove impurities. A yellow solution obtained as a precursor was then concentrated until a complex precipitated and solids were separated by filtration and dried under reduced pressure (1 mmHg) to obtain trans-RuCl2[(S)-xylbinap][(S,S)-dpen] (214.8 mg; 0.192 mmol; yield: 77%) as a yellow powder. [XylBINAP] and [xylbinap] are abbreviations for 2,2′-bis(di-3,5-xylylphosphino)-1,1′-binaphthyl. [00032] The abovementioned trans-RuCl2[(S)-xylbinap] [(S,S)-dpen] (89.5 mg; 0.08 mmol) and sodium borohydride (75.6 mg; 2.0 mmol) (made by Nacalai Tesque, Inc.) were then weighed and placed in a 20 mL Schlenk reaction tube equipped with a stirrer coated with polytetrafluoroethylene, and after depressurizing the interior of the vessel to eliminate air, argon was introduced. After then adding a 1:1 volume ratio mixed solvent of benzene/ethanol (6 mL) with a syringe, heating in an oil bath set to 65 C. was performed for 5 minutes under an argon atmosphere. The reaction solution was thereafter stirred for 30 minutes at room temperature. After then drying and solidifying the crude product by distilling off the solvent under reduced pressure (1 mmHg), hexane (5 mL) was added under an argon gas flow to dissolve as much of a yellow product as possible and then the excess sodium borohydride was eliminated by filtration by celite (0.5 g). A yellow filtrate thus obtained was concentrated to approximately 1 ml by depressurization (1 mm Hg) and yellow solids thus precipitated were separated by filtration through a glass filter and dried under reduced pressure (1 mmHg) to obtain trans-RuH(eta1-BH4)[(S)-xylbinap][(S,S)-dpen] (38.3 mg; yield: 45%; see formula (4) below) as a yellow powder. Decomposition temperature: 220 C.; 1HNMR(400 MHz, C6D6) delta-13.67(t, 1, J=23.2 Hz, RuH), -0.48(brs, 4, BH4), 1.59(brs, 12, 4 CH3), 1.78(s, 6, 2CH3), 2.00(s, 6, 2CH3), 2.28-2.35(m, 2, 2NHH), 3.62-3.67(m, 1, CHNH2), 3.76-3.81(m, 2,2CHNH2), 4.09 (dd, 1, J=9.6 and 18.2 Hz, CHNH2), 5.77-8.38(m, 34, aromatics); 31PNMR(161.7 MHz, C6D6) delta73.1(d, J=41.4 Hz), 76.8(d, J=41.4 Hz); IR(toluene)2319(s), 1850(s), 1125(s)cm-1; ESI-MS m/z1063.33([M-H]+), theoretical value (C66H68BN2P2Ru): 1063.40.

29841-69-8, 29841-69-8 (1S,2S)-(-)-1,2-Diphenylethylenediamine 6931238, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; Nagoya Industrial Science Research Institute; US6720439; (2004); B1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

29841-69-8, (1S,2S)-(-)-1,2-Diphenylethylenediamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Chloro-propanoic acid (4.34 g, 0.04 mol) was dissolved in 5.0 mL of water on ice bath and carefully neutralized with cold water solution of 5.0 mL NaOH (1.60 g, 0.04 mol). Meso-1,2-diphenyl-ethylenediamine (4.24 g, 0.02 mol) was added to this solution. The mixture was being stirred for 4 h at 90 C, and during this period 5.0 mL NaOH water soltion (1.60 g, 0.04 mol) was introduced. After that, 5.6 mL 6 mol/L HCl was added and resulting solution was evaporated to the volume of 7.0 mL; 6.0 mL conc. HCl, 6.0 mL of ethanol and 6.0 mL of ether were added to the mixture. The white precipitate of meso-1,2-diphenyl-ethylenediamine-N,N’-di-3-propanoic acid dihydrochloride monohydrate, H2-1,2-dpheddp 2HCl H2O was separated by filtration and refined with solution water: ethanol = 1: 2. Yield: 4.00 g (44.69%). Anal. Calcd. for H2-1,2-dpheddp*2HCl*H2O = C20H28Cl2N2O5 (Mr = 447.344): C, 53.69; H, 6.31; N, 6.26. Found: C, 53.88; H, 6.70; N, 6.08.

29841-69-8, 29841-69-8 (1S,2S)-(-)-1,2-Diphenylethylenediamine 6931238, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Radi?, Gordana P.; Glodovi?, Verica V.; Ratkovi?, Zoran R.; Novakovi?, Sladana B.; Garcia-Granda, Santiago; Roces, Laura; Menendez-Taboada, Laura; Radojevi?, Ivana D.; Stefanovi?, Olgica D.; ?omi?, Ljiljana R.; Trifunovi?, Sre?ko R.; Journal of Molecular Structure; vol. 1029; (2012); p. 180 – 186;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29841-69-8,(1S,2S)-(-)-1,2-Diphenylethylenediamine,as a common compound, the synthetic route is as follows.

A solution of sulfonyl chloride B (10 mmol) in dichloromethane (25 mL) was slowlyadded to a stirred solution of diamine A (10 mmol), NEt3 (11 mmol) in dichloromethane(25 mL). The resulting mixture was stirred for another 3 hr, washed twice with water (25mL) and dried over Na2SO4. The solvent was removed in vacuo to give a white solid C. Toa solution of D in CH2Cl2 (40 mL) was added NEt3 (11 mmol), isobutyl carbonochloridate(11 mmol) at 0 oC under stirring. After 10 min, C was added. The reaction was allowed towarm to room temperature for another 3 hr. The mixture was washed with 1 M KHSO4solution, saturated NaHCO3 solution, and brine, dried over anhydrous Na2SO4 andconcentrated to get a white solid E. Then, TFA (10 mL) was added to the CH2Cl2 (10 mL)solution of E, and stirred until the reaction finished (1 hr). The pH value of the mixture wasbrought into the range of 10-12 by the addition of 2 N NaOH solution. The aqueousphase was extracted with CH2Cl2 (3 ¡Á 30 mL). The combined organic phase was washedwith brine, dried over anhydrous Na2SO4, and concentrated and purified through flashchromatograph as a white solid F (70% yield).

29841-69-8, The synthetic route of 29841-69-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Tang, Yu; Xu, Jian; Yang, Jian; Lin, Lili; Feng, Xiaoming; Liu, Xiaohua; Chem; vol. 4; 7; (2018); p. 1658 – 1672;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI