Category: 929-75-9

Application of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: 0.41 mmol of polyethylene glycol diamine,DIPEA105 mg, 4-fluoro-2- (2,6-dioxopiperidin-3-yl) ethindol-1,3-one,Add DMF 2mL, 90 C for 12 h. Cool to room temperature,Add water 20mL, ethyl acetate extraction,The extract is saturated with saline,Dried over anhydrous magnesium sulfate,Evaporated under reduced pressure,Silica gel column chromatography (methanol: dichloromethane 1; 10)Intermediate 7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Patent; Jilin University; Lu Haibin; Wang Shihui; Li Haiyan; Wang Chunhe; Deng Jiayu; Feng Mingming; Guo Yu; Su Runping; Jin Xiangqun; (26 pag.)CN106543185; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, A new synthetic method of this compound is introduced below., Safety of 1,11-Diamino-3,6,9-trioxaundecane

General procedure: A two-neck flaskequipped with a magnetic stirrer and reflux condenser, flushed with dry argon, was charged withcorresponding triazacycloalkane derivative 8-10 (0.15-0.29 mmol), Pd(dba)2 (16 mol%),DavePhos (18 mol%), and absolute dioxane (10-15 ml). The mixture was stirred for 2-3 min,then corresponding oxadiamine (0.15-0.29 mmol) was added followed by tBuONa (0.45-0.9mmol). The reaction mixture was stirred at reflux for 24 h, cooled down to ambient temperature,the residue was filtered off, washed with dichloromethane (5 ml), combined organic fractionswere evaporated in vacuo, and the residue was chromatographed on silica gel using a sequenceof eluents CH2Cl2,CH2Cl2-MeOH 100:1-2:1, CH2Cl2-MeOH- NH3aq100:20:1-10:4:1.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Chernichenko, Nataliya M.; Shevchuk, Vadim N.; Averin, Alexei D.; Maloshitskaya, Olga A.; Beletskaya, Irina P.; Synlett; vol. 28; 20; (2017); p. 2800 – 2806;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure for the preparation of compounds 10-15 (B) (0016) The appropriate diamines were added to compound 1a and Na2CO3 (2eq.) with stirring in DMF (5mL). The mixture was stirred overnight at room temperature. After completion, as judged by TLC, the solvent was evaporated under reduced pressure. The mixture was resolved in EtOAc and washed twice with water and brine. The organic layer was dried over Na2SO4, then filtered and concentrated. The crude product was purified by column chromatography (CH2Cl2/MeOH, 25/1 v/v) to give the target compound as a white solid.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Fei; Peng, Yiyun; Wang, Qi; Shi, Yongying; Si, Longlong; Wang, Han; Zheng, Yongxiang; Lee, Emily; Xiao, Sulong; Yu, Maorong; Li, Yingbo; Zhang, Chuanling; Tang, Hengli; Wang, Chunguang; Zhang, Lihe; Zhou, Demin; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 258 – 268;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of 3,4-dihydroxycinnamic acid (497mg, 2.76mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (794mg, 4.14mmol), 1-hydroxybenzotriazole (HOBt) (559mg, 4.14mmol), Et3N (0.58mL, 4.14mmol) in anhydrous DMF (10mL) was stirred under an atmosphere of argon for 10minat 26C. Propane-1,3-diamine (102mg, 1.38mmol) was added, and the mixture was stirred for 18hat 26C. The mixture was concentrated under reduced pressure to give a crude coupling product of the title compound (2). To facilitate isolation, the coupling product was treated with Ac2O (10mL) in pyridine (10mL) at 26C for 12h. The mixture was concentrated, and extracted with EtOAc and water for three times. The organic layers were combined and washed with water (10mL) and brine (10mL). The organic phase was dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (EtOAc elution) to afford the acetylation compound. To a solution of the acetylation compound in MeOH (10mL) was added K2CO3 (13mg, 0.13mmol). The mixture was stirred for 0.5hat 26C, and then acidified to pH 5 by addition of Dowex 50WX8-200 cationic exchange resin. The resin was then removed by filtration. The filtrate was concentrated, and purified by silica gel chromatography (EtOAc, then MeOH/CH2Cl2 1:4) to give pure compound 2 (146mg, 27% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Article; Tu, Ling-Hsien; Tseng, Ning-Hsuan; Tsai, Ya-Ru; Lin, Tien-Wei; Lo, Yi-Wei; Charng, Jien-Lin; Hsu, Hua-Ting; Chen, Yu-Sheng; Chen, Rong-Jie; Wu, Ying-Ta; Chan, Yi-Tsu; Chen, Chang-Shi; Fang, Jim-Min; Chen, Yun-Ru; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 393 – 404;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 929-75-9, These common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A two-neck flask equipped with a magnetic stirrer and reflux condenser, flushed with dry argon, was charged with diazacrown derivative 4-9 (0.2-0.25 mmol), Pd(dba)2 (8-16 mol%), BINAP or DavePhos ligand (9-18 mol%), absolute dioxane (10-12 mL), the reaction mixture was stirred for several minutes, then the corresponding polyamine (0.2-0.25 mmol) and NaOt-Bu (0.6-0.75 mmol) were added, and the reaction mixture was stirred at reflux for 24 h. After cooling down to room temperature the residue was filtered off, washed with CH2Cl2 (5-10 mL), the combined organic fractions were evaporated in vacuo, the residue was dissolved in CH2Cl2 (10 mL), washed with distilled water (3 × 10 mL), dried over 4A molecular sieves, and the solvent was evaporated in vacuo. The solid residue was chromatographed on silica gel (40-60 mum) using a sequence of eluents: CH2Cl2, CH2Cl2-MeOH 100:1-3:1, CH2Cl2-MeOH-NH3(aq) 100:20:1-10:4:1.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yakushev, Alexei A.; Chernichenko, Nataliya M.; Anokhin, Maxim V.; Averin, Alexei D.; Buryak, Alexei K.; Denat, Franck; Beletskaya, Irina P.; Molecules; vol. 19; 1; (2014); p. 940 – 965;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 929-75-9, These common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

0.500 g of cinnamic acid, 0.295 g of 1,11-diamino-3,6,9-trioxadecane, 0.647 g of EDCI, 0.037 g of DMAP, 10 mL of anhydrous dichloromethane were sequentially added to the round bottom flask, and stirred at room temperature. After 12 h, 20 mL of dichloromethane was added, and the mixture was washed successively with brine (1×30 mL) and water (2×30 mL), dried over anhydrous sodium sulfate, filtered, evaporated to dryness Chloroform/methanol = 35:1; 50:4) gave 0.178 g of a pale yellow oily substance, yield 28% (see Figure 49 for the synthetic route and Figure 50 for the characterization)

Statistics shows that 1,11-Diamino-3,6,9-trioxaundecane is playing an increasingly important role. we look forward to future research findings about 929-75-9.

Reference:
Patent; Chinese Academy Of Medical Sciences Biomedical Engineering Institute; Liu Tianjun; Wang Jiawen; Li Guoliang; Hong Ge; Wang Wenzhi; (37 pag.)CN110229110; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Diester1 (1mmol) and the appropriate diamine2-6 (1mmol) were dissolved in dry methanol (50mL) and sodium methoxide (2mmol) was added. A mixture was stirring for 72hat room temperature. After completion of the reaction (controlled by TLC), the solvent was evaporated under reduced pressure and the oily residue was purified by column chromatography (1-5% MeOH in CH2Cl2). All the macrocyclic products obtained in this way are colourless solids, stable to air.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pikus, Grzegorz; Jurczak, Janusz; Tetrahedron; vol. 72; 16; (2016); p. 1928 – 1932;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A two-necked flask equipped with a condenser and magnetic stirrer, flushed with dry argon, wascharged with compounds 14 or 15 (0.2 mmol), Pd(dba)2 (18.4 mg, 16 mol%), RuPhos (16.8 mg,18 mol%), 10 ml absolute dioxane was added followed by corresponding oxadiamine 3a-d (0.4mmol) and sodium tert-butoxide (1.2 mmol, 115 mg). The reaction mixture was stirred at refluxfor 24 h, cooled down to room temperature, the residue was filtered off and washed with 5 mldichloromethane. The combined organic fractions were evaporated in vacuo, the residue wasdissolved in 5 ml dichloromethane, washed by water (3×5 ml), dried over molecular sieves 4A,the solvent was evaporated in vacuo and chromatographed on silica gel using a sequence ofeluents: CH2Cl2, CH2Cl2/MeOH 100:1 – 3:1, CH2Cl2/MeOH/NH3aq 100:20:1 – 100:20:4.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chernichenko, Nataliya M.; Averin, Alexei D.; Beletskaya, Irina P.; Letters in Organic Chemistry; vol. 15; 5; (2018); p. 425 – 430;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: All macrocyclic compounds were obtained as previously described. 20,21 The corresponding diester (1-3) (10 mmol) and diamine (4-8) (10 mmol) were dissolved in MeOH (100 ml). The reaction mixture was stirred for 7 d at rt. After completion of the reaction (monitored by TLC), the solvent was evaporated and the residue was puriofied by chromatography on a silica gel column using 0-5% solutions of MeOH/CH2Cl2. Analytical and spectroscopic data are collected in the Supplementary Materials.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Pikus, Grzegorz; Pa?niczek, Ewa; Jurczak, Janusz; Arkivoc; vol. 2017; 2; (2017); p. 534 – 545;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 929-75-9, Formula: C8H20N2O3

To 4-carboxymethyl-7-[1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1H-1,2,3-triazol-4-yl]-2H-chromen-2-one (7a, 200 mg, 0.273 mmol) and 1,11-diamino-3,6,9-trioxaundecane (8c, 53 mg, 0.273 mmol) in THF (10 mL) at room temperature was added benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (121 mg, 0.273 mmol), and the mixture was stirred at the same temperature for 1 h. The solvent was removed, and the resulting slurry was diluted with saturated aqueous NaHCO3 and extracted with methylene chloride several times. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on a silica gel column with methylene chloride and MeOH (7:1) to give the desired product 10e (113 mg, 46%). Mp 303.9+/-0.7 C; 1H NMR (500 MHz, DMF-d7): delta=8.92 (s, 1H), 8.44 (br t, J=5.6 Hz, 1H), 7.99 (d, J=8.3 Hz, 1H), 7.94 (dd, J=8.3 and 1.5 Hz, 1H), 7.89 (d, J=1.5 Hz, 1H), 6.52 (s, 1H), 4.74 (t, J=7.0 Hz, 2H), 3.92 (s, 2H), 3.78 (m, 2H), 3.63-3.67(m, 2H), 3.60-3.63 (m, 2H), 3.57-3.60 (m, 4H), 3.55 (t, J=5.6 Hz, 2H), 3.40 (q, J=5.6 Hz, 2H), 3.24-3.33 (m, 2H), 2.43-2.56 (m, 2H), 2.31-2.31 ppm (m, 2H); 13C NMR (125 MHz, DMF-d7): delta=168.4, 160.2, 154.4, 151.1, 145.7, 135.0, 126.6, 123.2, 121.3, 119.1, 116.0, 112.9, 70.35, 70.27, 70.21, 70.18, 69.5, 67.2, 49.1, 40.1, 39.94, 39.91, 39.7, 39.6, 39.5, 39.4, 39.2, 27.8 (t, J=19.2 Hz), 21.6 ppm (t, J=3.5 Hz); IR (ATR, neat): nu=2925, 1719 (CO), 1654 (CO), 1622, 1238, 1203, 1147, 1056, 1027, 1009, 1004, 832, 823, 763 cm-1; MS (ESI): m/z: 906 [M+H+]; HRMS (EI): m/z calcd for C32H32F17N5O6: 905.2081 [M+]; [M+] not found.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,11-Diamino-3,6,9-trioxaundecane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jeon, Moon-Kook; Kang, Myoung-Ku; Park, Koon Ha; Tetrahedron; vol. 68; 30; (2012); p. 6038 – 6053;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem