Month: September 2020

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO269,mainly used in chemical industry, its synthesis route is as follows.,2879-20-1

General procedure: To a stirred solution of 1 (0.84 mmol) in 5 N NaOH (3 mL) was added 2-heptanone (7.18 mmol) dropwise. The reaction mixture was heated to 60 C and kept for 3 h under stirring conditions. After cooling, the mixture was then extracted with CHCl3/MeOH (10:1, v/v) in a separatory funnel. The organic layer was washed to neutral status using water, dried using anhydrous MgSO4, and filtered. The filtrate was concentrated under reduced pressure to yield a crude intermediate. The crude intermediate was dissolved in anhydrous tetrahydrofuran (8 mL), followed by adding HOAc (1.0 mL) and formaldehyde (15.06 mmol) to the solution. The reaction mixture was kept refluxing for 3 h. After the reaction was halted and the reaction mixture cooled, evaporation under reduced pressure was done to remove the solvent from the reaction mixture. The residue was acidified using aqueous 2 N HCl (2 mL), and the solution was stirred at room temperature for 1 h, and extracted with CHCl3/MeOH (10:1, v/v) in a separatory funnel. The organic layer was dried using anhydrous MgSO4, filtered, and concentrated under reduced pressure to yield the crude product. The crude product was purified using silica gel CC (elutated with CHCl3:MeOH, 20:1, v/v) to yield 3e (97 mg, 23.3% yield) as a yellow solid.

With the synthetic route has been constantly updated, we look forward to future research findings about 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone,belong benzodioxans compound

Reference£º
Article; Zhang, Zhi-Hui; Yan, Yu; Deng, An-Jun; Zhang, Hai-Jing; Li, Zhi-Hong; Yuan, Tian-Yi; Fang, Lian-Hua; Wu, Lian-Qiu; Du, Guan-Hua; Qin, Hai-Lin; Chinese Chemical Letters; vol. 29; 1; (2018); p. 131 – 135;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO467,mainly used in chemical industry, its synthesis route is as follows.,17413-10-4

General procedure: A solution of carboxylic acid (0.5 mmol) and HATU (0.55 mmol)in anhydrous DMF (2 mL) was stirred at ambient temperature for10 min. To this solution, DIPEA (0.6 mmol) and correspondingamine (0.54 mmol) were added successively and the mixture wasstirred for 18 h. After concentration under reduced pressure, thereaction mixture was treated with water (5 mL) and extracted withDCM (2 5 mL). After evaporation of the solvent, the residue wascrystallized from an appropriate solvent or subjected to columnchromatography on silica gel (DCM/MeOH) or preparative HPLC

With the synthetic route has been constantly updated, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)methanamine,belong benzodioxans compound

Reference£º
Article; Krasavin, Mikhail; Gureyev, Maxim A.; Dar’in, Dmitry; Bakulina, Olga; Chizhova, Maria; Lepikhina, Anastasia; Novikova, Daria; Grigoreva, Tatyana; Ivanov, Gleb; Zhumagalieva, Aisulu; Garabadzhiu, Alexander V.; Tribulovich, Vyacheslav G.; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2651 – 2673;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4442-54-0,2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,as a common compound, the synthetic route is as follows.

Method I Ba (1 mmol) and 2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid (or 2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. 4.5.10 (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(3-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone (C10) White crystal, mp: 105-107 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.19-3.24 (d, J = 16.2 Hz, 1H), 3.65-3.73 (m, 1H), 4.32 (t, J = 2.1 Hz, 4H), 5.72-5.78 (m, 1H), 6.78 (s, 1H), 6.95-7.09 (m, 3H), 7.23-7.26 (m, 1H), 7.44-7.53 (m, 4H), 7.57 (s, 1H), 7.62-7.65 (d, J = 8.4 Hz, 2H). MS (ESI): 403.14 (C24H20FN2O3, [M+H]+). Anal. Calcd for C24H19FN2O3: C, 71.63; H, 4.76; F, 4.72; N, 6.96; O, 11.93. Found: C, 71.37; H, 4.74; N, 6.98., 4442-54-0

4442-54-0 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid 2758833, abenzodioxans compound, is more and more widely used in various fields.

Reference£º
Article; Yang, Yu-Shun; Li, Qing-Shan; Sun, Shuai; Zhang, Yan-Bin; Wang, Xiao-Liang; Zhang, Fei; Tang, Jian-Feng; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6048 – 6058;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,4442-54-0,Molecular formula: C9H8O4,mainly used in chemical industry, its synthesis route is as follows.,4442-54-0

Method I Ba (1 mmol) and 2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid (or 2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. (3-(4-Bromophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone (C2) Yellow crystal, mp: 189-190 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.12-3.17 (d, J = 10.5 Hz, 1H), 3.70-3.77 (m, 1H), 4.29-4.34 (t, J = 4.5 Hz, 4H), 5.79-5.82 (m, 1H), 6.90-6.95 (d, J = 11.7 Hz, 2H), 7.29-7.42 (m, 3H), 7.53-7.59 (m, 4H), 7.65-7.67 (m, 3H). MS (ESI): 463.06 (C24H20BrN2O3, [M+H]+). Anal. Calcd for C24H19BrN2O3: C, 62.22; H, 4.13; Br, 17.25; N, 6.05; O, 10.36. Found: C, 62.07; H, 4.12; N, 6.06.

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,belong benzodioxans compound

Reference£º
Article; Yang, Yu-Shun; Li, Qing-Shan; Sun, Shuai; Zhang, Yan-Bin; Wang, Xiao-Liang; Zhang, Fei; Tang, Jian-Feng; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6048 – 6058;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

4442-54-0, 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid (9.0 g, 50 mmol) in methanol (50 mL) containing concentrated H2SO4 (5 mL) was refluxed overnight. Water (100 mL) was added, the organic phases were washed with saturated NaCl (100 mL) and dried over Na2SO4, and the solvents were evaporated., 4442-54-0

As the paragraph descriping shows that 4442-54-0 is playing an increasingly important role.

Reference£º
Article; Sun, Juan; Cao, Ning; Zhang, Xiao-Min; Yang, Yu-Shun; Zhang, Yan-Bin; Wang, Xiao-Ming; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4895 – 4902;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,4442-54-0,Molecular formula: C9H8O4,mainly used in chemical industry, its synthesis route is as follows.,4442-54-0

Method I Ba (1 mmol) and 2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid (or 2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. 4.5.14 (3-(4-Bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone (C14) White crystal, mp: 140-141 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.23-3.29 (d, J = 17.1 Hz, 1H), 3.80-3.87 (m, 1H), 4.35-4.37 (t, J = 3.9 Hz, 4H), 5.63-5.69 (m, 1H), 6.90-6.96 (m, 2H), 7.11 (m, 1H), 7.33-7.35 (d, J = 6.6 Hz, 1H), 7.47-7.50 (m, 4H), 7.59 (s, 1H), 7.66-7.69 (d, J = 8.4 Hz, 2H). MS (ESI): 481.05 (C24H19BrFN2O3, [M+H]+). Anal. Calcd for C24H18BrFN2O3: C, 59.89; H, 3.77; Br, 16.60; F, 3.95; N, 5.82; O, 9.97. Found: C, 59.72; H, 3.74; N, 5.82.

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,belong benzodioxans compound

Reference£º
Article; Yang, Yu-Shun; Li, Qing-Shan; Sun, Shuai; Zhang, Yan-Bin; Wang, Xiao-Liang; Zhang, Fei; Tang, Jian-Feng; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6048 – 6058;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)methanamine,17413-10-4,Molecular formula: C9H11NO2,mainly used in chemical industry, its synthesis route is as follows.,17413-10-4

A mixture of compound 5 (50 mg, 0.127 mmol), (2,3-dihydrobenzo[b]-[1,4] dioxin-6-yl) methanamine (40 mg, 0.242 mmol), and DIPEA (0.1 mL, 0.127 mmol) in EtOH (0.6 mL) was placedinto sealed tube and stirred at 160C under microwave irradiation for 1 h. The mixture was cooled and purified by silica gel column chromatography (EtOAc-n-hexane; 22 : 67) to yield 6a(20 mg, 30%) as a colorless solid. 1H-NMR (400 MHz, CDCl3) delta: 8.60 (1H, br s), 8.28 (1H, d,J=2.0 Hz), 7.58 (1H, d, J=2.4 Hz), 7.45 (1H, br s), 7.34 (1H,d, J=8.8 Hz), 7.31 (1H, s), 7.23 (1H, d, J=8.8 Hz), 6.87 (1H,d, J=1.2 Hz), 6.82 (1H, d, J=1.2 Hz), 6.81 (1H, s), 6.61 (1H, t,J=55.2 Hz), 6.27 (1H, br s), 4.60 (2H, d, J=5.2 Hz), 4.56 (2H,d, J=5.6 Hz), 4.24 (4H, s), 2.43 (3H, s), 1.94 (1H, s), 1.59 (6H,s). 13C-NMR (100 MHz, CDCl3) delta: 167.3, 156.7, 154.9, 143.5,142.7, 137.6, 135.9 (t, J=4.3 Hz), 135.7, 132.8 (t, J=20.9 Hz),132.5, 131.7, 130.1 (t, J=2.1 Hz), 125.4 (t, J=7.4 Hz), 120.7,117.3, 116.6, 114.1 (t, J=238 Hz), 108.9, 106.0, 94.3, 79.2,65.7, 64.4, 64.3, 44.4, 43.5, 31.6, 18.2. MS (ESI) m/z: 522.1(M+H)+. FAB-MS m/z: 522.2230 (Calcd for C29H30F2N3O4+:522.2204). HPLC purity 95.1% (6.14 min, method A).

With the synthetic route has been constantly updated, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)methanamine,belong benzodioxans compound

Reference£º
Article; Takahashi, Bitoku; Funami, Hideaki; Shibata, Makoto; Maruoka, Hiroshi; Koyama, Makoto; Kanki, Satomi; Muto, Tsuyoshi; Chemical and Pharmaceutical Bulletin; vol. 63; 10; (2015); p. 825 – 832;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone,2879-20-1,Molecular formula: C10H10O3,mainly used in chemical industry, its synthesis route is as follows.,2879-20-1

General procedure: Carbonyl substrate, 0.02 mol, was added in portions to a suspension of 0.01 mol NaBH4 in 0.3 mol of the corresponding alcohol solvent, and the mixture was stirred for 2-2.5 h at 20C. The resulting boron derivatives of benzyl alcohols were decomposed with 10% aqueous HCl (3.7 mL), and the mixture was stirred for a required time at a required temperature(see Tables 1-5), cooled, and poured into 200 mL of cold water. The products were extracted with diethylether (2 ¡Á 40 mL), the combined extracts were washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off on a rotary evaporator, and the residue was analyzed by 1H NMR. If necessary,benzyl ethers were isolated by chromatography. Alcohol coreactants poorly soluble in water were removed from the diethyl ether extracts by vacuum distillation, and the target ethers ware isolated from the still residue. Ethers 2a [9], 2c [3], 2h, 4a [10], 4b [11], 4i,4l, 7e, 10c, 10d, 10e [4], and 13a [12] were described previously. Ethers 2b, 2d-2g, 2i, 4c-4h, 4j, 4k, 4m-4w, 7a-7d, 7f, 7g, and 13b-13f are mobile liquids, and 7h-7j, 10a, 10b, and 10f-10i are viscous liquids.

With the synthetic route has been constantly updated, we look forward to future research findings about 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone,belong benzodioxans compound

Reference£º
Review; Mochalov; Fedotov; Trofimova; Zefirov; Russian Journal of Organic Chemistry; vol. 52; 4; (2016); p. 503 – 512; Zh. Org. Khim.; vol. 52; 4; (2016); p. 503 – 512,10;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO25,mainly used in chemical industry, its synthesis route is as follows.,4442-54-0

To a stirred solution of 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid 1a (1.80?g, 10?mmol) in MeOH (20?mL) was added SOCl2 (1.45?mL, 20?mmol) dropwise at 0?¡ãC over 1?h. The mixture was further stirred 12?h at 50?¡ãC. The solution was cooled to room temperature and diluted with water (25?mL). MeOH was evaporated and the pH adjusted to ?6 with aqueous NaHCO3. The mixture was extracted three times with EtOAc and successively washed with brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give 2a (1.6?g, 83percent) as a colorless solid. 1H NMR (DMSO-d6, 500?MHz): delta [ppm]?=?3.80 (3H, s), 4.19 (2H, m), 4.23 (2H, m), 6.80 (1H, m), 7.47 (2H, m). 13C NMR (DMSO-d6, 125?MHz): delta [ppm]?=?50.5, 62.7, 63.2, 115.7, 117.6, 122.0, 141.7, 146.4, 165.2. EI-MS: m/z 194 (M+).

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,belong benzodioxans compound

Reference£º
Article; Lo Monte, Fabio; Kramer, Thomas; Gu, Jiamin; Brodrecht, Martin; Pilakowski, Johannes; Fuertes, Ana; Dominguez, Juan Manuel; Plotkin, Batya; Eldar-Finkelman, Hagit; Schmidt, Boris; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 26 – 40;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO26,mainly used in chemical industry, its synthesis route is as follows.,2879-20-1

General procedure: 1a-j (0.0299 – 0.0532 g, 0.299 mmol, 1 eq.), 2a-d (0.0166 – 0.228 g, 0.224 mmol, 0.75 eq.), FeCl3 (0.0145 g, 0.0897 mmol, 0.3 eq.), (NH4)2S2O8 (0.1363 g, 0.598 mmol, 2 eq.), and DCE / CCl4 (0.75 mL, 1 / 1) were stirred in Schott culture tubes (H ¡Á diam. 160 mm ¡Á 16 mm) at 120 C for 3 h. Further, after adding a solution of 2a-d (0.055 – 0.0763, 0.0748 mmol, 0.25 eq.) and DCE / CCl4 (0.08 mL, 1 / 1), the reaction mixture was stirred at 120 C for 3 h (3 times at 3-hour intervals). Next it was stirred at 120 C for 12 h. The yields of 3a-f,a-d were determined by 1H NMR (CDCl3) after the filtration of the reaction mass through a thin pad (0.4 – 0.5 cm) of silica gel (0.015 – 0.040 mm) using 20 mL of DCM and evaporation of solvent in vacuum. Products 3c,b and 3d,a-d were isolated by gradient flash chromatography (eluent: petroleum ether / ethyl acetate).

With the synthetic route has been constantly updated, we look forward to future research findings about 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone,belong benzodioxans compound

Reference£º
Article; Arzumanyan, Ashot V.; Tetrahedron Letters; vol. 58; 50; (2017); p. 4667 – 4671;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem