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Product Details of [ 56683-55-7 ]

CAS No. :56683-55-7 MDL No. :MFCD00143276
Formula : C15H20O7 Boiling Point : -
Linear Structure Formula :- InChI Key :FBNLTQGIRRAGRY-UHFFFAOYSA-N
M.W :312.32 Pubchem ID :2724800
Synonyms :

Safety of [ 56683-55-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 56683-55-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 56683-55-7 ]

[ 56683-55-7 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 41757-95-3 ]
  • [ 56683-55-7 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide; bromine In water at 0 - 10℃;
83% With sodium hydroxide; bromine at 20℃; for 5h;
75% With sodium hydroxide; bromine
  • 2
  • [ 56683-55-7 ]
  • [ 104989-11-9 ]
  • 1,3,3-Trimethyl-9'-carboxybenzo-15-crown-5-spiro<indoline-naphthoxazine> [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane for 24h; Ambient temperature;
  • 3
  • [ 56683-55-7 ]
  • [ 65558-67-0 ]
YieldReaction ConditionsOperation in experiment
65.1% With borane-THF In tetrahydrofuran for 3h; Ambient temperature;
  • 4
  • [ 56683-55-7 ]
  • [ 54664-43-6 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane for 0.5h; Reflux; 3.6.2. Method 2 312 mg (1 mmol) 4-carboxybenzo-15-crown-5 ether were dissolved in 25 mL dichloretane, and 0.5 mL thionyl chloride and one drop of DMF were added. The mixture was refluxed for 0.5 h, and then the solvent and the excess of thionyl chloride were removed in vacuo using a rotavap, yielding quantitatively the corresponding acid chloride. The acid chloride was dissolved in 25 mL DCM, and 203 mg 4-AAP (1 mmol) dissolved in 25 mL DCM were added, followed by 1 mL triethylamine. The reaction mixture was left overnight at room temperature, and the next day was extracted twice with 50 mL aqueous hydrochloric acid (1 M), and then twice with 50 mL aqueous sodium hydrogen carbonate (3%), followed by 50 mL water. The organic phase was then dried on anhydrous sodium sulfate, filtered off, and the solvent removed using a rotavap. The residue was chromatographied using a silica gel column (or preparative TLC plates) and ethyl acetate as eluent. Yields: ∼50%.Elemental analysis: C26H31N3O7, M = 497; calc.: C = 62.77%, H = 6.28%, N = 8.45%; found: C = 62.97%, H = 6.33%, N = 8.41%.1H NMR(CDCl3, δ ppm, J Hz): 8.87(bs, 1H, H-8); 7.56-7.21(m, 7H, H3, H-5, H-17-H-21); 6.73(bd, 1H, H-6, 8.0); 4.07(m, 4H, H-22, H-23); 3.92-3.66(m, 12H, H-CE); 3.05(s, 3H, H-15); 2.20(s, 3H, H-14).13C NMR(CDCl3, δ ppm): 165.93(C-7); 162.19(C-13); 151.93(C-16); 150.19(Cq); 148.48(Cq); 134.47(Cq); 129.38(C-18, C-20); 126.43(C-19); 124.80(C-17, C-21); 123.69(C-9); 121.51(C-5); 112.38(C-6); 113.02(C-3); 108.72(C-10); 71.04(CH2O); 70.36(CH2O); 69.24(CH2O); 68.65(CH2O); 35.96(C-15); 12.43(C-10).IR(ATR in solid, ν cm-1): 3454; 3272, 2925, 2870, 1645, 1591, 1494, 1452, 1297, 1266, 1213, 1128, 1048, 935, 761, 586.UV-Vis (methanol, λmax nm): 261.Rf (silicagel, ethyl acetate): 0.08.
100% With thionyl chloride In chloroform at 20℃; for 3h;
99% With pyridine; oxalyl dichloride In dichloromethane for 4h; Ambient temperature;
95% With thionyl chloride for 4h; Heating;
With thionyl chloride Heating;
With pyridine; oxalyl dichloride In dichloromethane for 6h; Ambient temperature;
With thionyl chloride In chloroform for 2h; Heating;
With thionyl chloride In toluene Heating;
With thionyl chloride In dichloromethane
With thionyl chloride In chloroform for 3h; Heating;
With thionyl chloride
With thionyl chloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide for 2h; Reflux; General procedure: To 2 mmol of nicotinic acid suspended in 30 mL of 1,2-dichloroethane were added two drops of DMF and 2 mL ofthionyl chloride, and the mixture was refluxed for 2 h; thesolvent and excess thionyl chloride were removed undervacuum, and to the residue were added 50 mL of DCM,2 mmol of benzocaine, and 5 mL of thiethylamine; the nextday, 50 mL of DCM were added, and the organic phaseextracted with 100 mL of diluted aqueous hydrochloricacid (10%), followed by aqueous sodium hydrogencarbonate (3%), and then dried using anhydrous sodiumsulphate. The removal of the DCM affords the crudecompound, which can be purified on preparative silica TLCplates, using DCM as an eluent.

Reference: [1]Location in patent: experimental part Remes; Paun; Zarafu; Tudose; Caproiu; Ionita; Bleotu; Matei; Ionita [Bioorganic Chemistry, 2012, vol. 41-42, p. 6 - 12]
[2]Kloos, Joey; Jansen, Nico; Houben, Menno; Casimiro, Anna; Lub, Johan; Borneman, Zandrie; Schenning, Albert P.H.J.; Nijmeijer, Kitty [Chemistry of Materials, 2021, vol. 33, # 21, p. 8323 - 8333]
[3]Haines, Alan H.; Hodgkisson, Ian; Smith, Christopher [Journal of the Chemical Society. Perkin transactions I, 1983, p. 311 - 318]
[4]Sakata, Kazunori; Shimoda, Manabu; Hashimoto, Mamoru [Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1593 - 1598]
[5]He, Gong-Xin; Wada, Fumio; Kikukawa, Kiyoshi; Shinkai, Seiji; Matsuda, Tsutomu [Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 541 - 548]
[6]Hedderwick, Robert J. M.; Hibbert, Frank; Gold, Victor [Journal of the Chemical Society. Perkin transactions II, 1991, # 5, p. 579 - 582]
[7]Nakajima, Masaki; Kimura, Keiichi; Shono, Toshiyuki [Analytical Chemistry, 1983, vol. 55, # 3, p. 463 - 467]
[8]Arafa, Ezzidin A.; Kinnear, Kenneth I.; Lockhart, Joyce C. [Journal of the Chemical Society. Chemical communications, 1992, # 1, p. 61 - 64] Kinnear, Kenneth I.; Mousley, David P.; Arafa, Ezzidin; Lockhart, Joyce C. [Journal of the Chemical Society, Dalton Transactions, 1994, # 24, p. 3637 - 3644]
[9]Gunter, Maxwell J.; Johnston, Martin R. [Tetrahedron Letters, 1992, vol. 33, # 13, p. 1771 - 1774]
[10]Gunter, Maxwell J.; Johnston, Martin R.; Skelton, Brian W.; White, Allan H. [Journal of the Chemical Society. Perkin transactions I, 1994, # 8, p. 1009 - 1018] Tokuhisa, Hideo; Yokoyama, Masaaki; Kimura, Keiichi [Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 7, p. 2123 - 2130]
[11]Leblanc; Berdague; Rault; Bayle; Judeinstein [Chemical Communications, 2000, # 14, p. 1291 - 1292]
[12]Paun, Anca; Zarafu, Irina; Caproiu, Miron T.; Draghici, Constantin; Maganu, Maria; Cotar, Ani I.; Chifiriuc, Mariana C.; Ionita, Petre [Comptes Rendus Chimie, 2013, vol. 16, # 7, p. 665 - 671]
  • 5
  • [ 56683-55-7 ]
  • [ 113475-61-9 ]
YieldReaction ConditionsOperation in experiment
66% With nitric acid In acetic anhydride; acetic acid at 80℃; for 1.5h;
  • 7
  • [ 201230-82-2 ]
  • [ 73368-13-5 ]
  • [ 56683-55-7 ]
YieldReaction ConditionsOperation in experiment
28% With sodium acetate In acetonitrile for 1h; Ambient temperature;
  • 8
  • [ 72299-76-4 ]
  • [ 56683-55-7 ]
YieldReaction ConditionsOperation in experiment
66% In potassium hydroxide; ethanol for 24h; Heating;
  • 9
  • [ 110-89-4 ]
  • [ 56683-55-7 ]
  • (benzo-15-crown-5)-4'-carboxylic acid piperidide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine In benzene at 70℃;
  • 10
  • [ 110-91-8 ]
  • [ 56683-55-7 ]
  • (benzo-15-crown-5)-4'-carboxylic acid morpholide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With triethylamine In benzene at 70℃;
  • 11
  • [ 56683-55-7 ]
  • rac-salsoline [ No CAS ]
  • (benzo-15-crown-5)-4'-carboxylic acid salsolid [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With triethylamine In benzene at 70℃;
  • 12
  • [ 56683-55-7 ]
  • (6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) [ No CAS ]
  • (benzo-15-crown-5)-4'-carboxylic acid salsolidide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With triethylamine In benzene at 70℃;
  • 13
  • [ 6066-82-6 ]
  • [ 56683-55-7 ]
  • NHS-benzo[15-crown-5]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.2% With dicyclohexyl-carbodiimide In various solvent(s) at 0℃; for 24h;
  • 14
  • benzo-15-crown-5-41-thiocarboxamide [ No CAS ]
  • [ 56683-55-7 ]
YieldReaction ConditionsOperation in experiment
33% With potassium hydroxide In 1,4-dioxane at 80 - 83℃; for 2h;
  • 15
  • [ 56683-55-7 ]
  • [ 39684-80-5 ]
  • [ 909804-21-3 ]
YieldReaction ConditionsOperation in experiment
94.2% With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2h; 1.1 To a solution of mixture of 4-carboxybenzo 15-crown-5 (0.77 g, 2.5 mmol, 1.1 equivalent (eq.)) and potassium carbonate (0.93 g, 6.7 mmol, 3.0 eq.) in anhydrous N,N-dimethylformamide (20.0 mL), a solution of 2-(Boc-amino)ethyl bromide (0.50 g, 2.2 mmol, 1.0 eq.) in anhydrous N,N-dimethylformamide (8.0 mL) was added, and the resulting mixture was stirred under Ar atmosphere at 50°C for 2 hours. The reaction mixture was filtered to remove potassium carbonate. The filtrate was added to dichloromethane (150 mL) and the resulting organic solution was washed with water (100 mL x 6). The obtained organic solution was dried over Na2SO4. The solvent was evaporated under vacuum to obtain yellow crystals (yield: 94.2%). 1H NMR (300 MHz; CDCl3, r.t., TMS, d / ppm) 1.44 (s, 9 H, CCH3), 3.50-3.55 (m, 2 H, NHCH2), 3.75-3.80 (m, 8 H, CH2 OCH2 CH2 OCH2), 3.90-3.95 (m, 4 H, ArOCH2CH2O), 4.15-4.20 (m, 4 H, ArOCH2CH2O), 4.35 (t, J = 5.1 Hz, 2 H, CH2 OCO), 4.85-4.95 (brs, 1 H, NH), 6.85 (d, J = 8.3 Hz, 1 H, ArH), 7.53 (s, 1 H, ArH), 7.67 (d, J = 8.3 Hz, 1 H, ArH). TLC : Rf = 0.4 (SiO2 chloroform: methanol = 20:1, v/v)
  • 16
  • [ 56683-55-7 ]
  • 3-amino-3-deoxy-β-cyclodextrin [ No CAS ]
  • N-(4'-carbonylbenzo-15-crown-5)-3-amino-3-deoxy-β-cyclodextrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 13h;
  • 17
  • [ 56683-55-7 ]
  • 6-amino-6-deoxy-β-cyclodextrin [ No CAS ]
  • N-(4'-carbonylbenzo-15-crown-5)-6-amino-6-deoxy-β-cyclodextrin [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 13h;
  • 18
  • [ 56683-55-7 ]
  • C37H55N3O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 86.2 percent / DCC / various solvent(s) / 24 h / 0 °C 2: 105 mg / CH2Cl2 / 24 h / 20 °C
  • 19
  • [ 638-56-2 ]
  • [ 56683-55-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaOH / ethanol / 48 h / Heating 2: KMnO4 / H2O
  • 20
  • [ 56683-55-7 ]
  • 6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecene-2-carboxylic acid 4-{4-[(E)-2-(2,3,4-tris-hexyloxy-phenyl)-vinyl]-phenylazo}-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride 2: pyridine / CHCl3
  • 21
  • [ 56683-55-7 ]
  • 6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecene-2-carboxylic acid 2,3-dimethyl-4-{4-[(E)-2-(2,3,4-tris-hexyloxy-phenyl)-vinyl]-phenylazo}-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride 2: pyridine / CHCl3
  • 22
  • [ 56683-55-7 ]
  • 6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecene-2-carboxylic acid 2,3-dimethoxy-4-{4-[(E)-2-(2,3,4-tris-hexyloxy-phenyl)-vinyl]-phenylazo}-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride 2: pyridine / CHCl3
  • 23
  • [ 56683-55-7 ]
  • 6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecene-2-carboxylic acid 2,3-bis-hexyloxy-4-{4-[(E)-2-(2,3,4-tris-hexyloxy-phenyl)-vinyl]-phenylazo}-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride 2: pyridine / CHCl3
  • 24
  • [ 112-60-7 ]
  • [ 56683-55-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / dimethylformamide / 6 h / Heating 2: NaOH / ethanol / 48 h / Heating 3: KMnO4 / H2O
  • 25
  • [ 60835-72-5 ]
  • [ 56683-55-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 54 percent / dimethylsulfoxide / 8 h / Heating 2: 66 percent / ethanol; aq. KOH / 24 h / Heating
  • 26
  • [ 56683-55-7 ]
  • C74H84N6O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / CHCl3 / 3 h / Heating 2: 61 percent / Py / CH2Cl2 / 4.5 h / Heating
Multi-step reaction with 2 steps 1: SOCl2 / CH2Cl2
  • 27
  • [ 56683-55-7 ]
  • C38H58N2O15Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / CHCl3 / 2 h / Heating 2: CHCl3 / 12 h / Ambient temperature
  • 28
  • [ 56683-55-7 ]
  • [ 4637-24-5 ]
  • [ 1013693-21-4 ]
YieldReaction ConditionsOperation in experiment
90% at 120℃; for 12h;
  • 29
  • [ 56683-55-7 ]
  • tribytyltin acetate [ No CAS ]
  • (CH3(CH2)3)3SnOCOC14H19O5*0.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In benzene byproducts: AcOH; equimolar amts., refluxing for 25 h; evapn. (vac.); elem. anal.;
  • 30
  • dibutyltin(IV) oxide [ No CAS ]
  • [ 56683-55-7 ]
  • [ 257280-62-9 ]
YieldReaction ConditionsOperation in experiment
98% In benzene stoich. amts., refluxing for 48 h; evapn. (vac.), recrystn. (petroleum ether/CH2Cl2); elem. anal.;
  • 31
  • [ 179091-70-4 ]
  • [ 56683-55-7 ]
  • C32H46N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 32
  • [ 56683-55-7 ]
  • [ 35373-95-6 ]
  • C28H38N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 33
  • [ 56683-55-7 ]
  • (S)-2-amino-N-hexyl-3-phenylpropanamide [ No CAS ]
  • C30H42N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 34
  • [ 56683-55-7 ]
  • [ 852331-99-8 ]
  • C34H50N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 35
  • [ 56683-55-7 ]
  • C14H30N2O [ No CAS ]
  • C29H48N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 36
  • [ 56683-55-7 ]
  • C13H28N2O [ No CAS ]
  • C28H46N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 37
  • [ 56683-55-7 ]
  • [ 84004-98-8 ]
  • C29H48N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 38
  • [ 56683-55-7 ]
  • (S)-2-amino-N-octylpropanamide [ No CAS ]
  • C26H42N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 39
  • [ 56683-55-7 ]
  • [ 97515-33-8 ]
  • C25H40N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
  • 40
  • [ 56683-55-7 ]
  • C30H51NO5 [ No CAS ]
  • C45H69NO11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;
  • 41
  • [ 56683-55-7 ]
  • octadecyl N-(tert-butoxycarbonyl)-L-tyrosinate [ No CAS ]
  • C47H73NO11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;
  • 42
  • [ 56683-55-7 ]
  • C24H39NO5 [ No CAS ]
  • C39H57NO11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;
  • 43
  • [ 56683-55-7 ]
  • C26H43NO5 [ No CAS ]
  • C41H61NO11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;
  • 44
  • [ 56683-55-7 ]
  • tetradecyl N-(tert-butoxycarbonyl)-L-tyrosinate [ No CAS ]
  • C43H65NO11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;
  • 45
  • [ 56683-55-7 ]
  • [ 112-71-0 ]
  • C29H48O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 18h;
  • 46
  • [ 56683-55-7 ]
  • [ 155130-15-7 ]
  • C32H46O14S [ No CAS ]
  • 47
  • [ 56683-55-7 ]
  • [ 4549-32-0 ]
  • C23H35BrO7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate In acetonitrile at 85℃; for 12h;
  • 48
  • [ 56683-55-7 ]
  • [ 37688-96-3 ]
  • C29H47BrO7 [ No CAS ]
  • 49
  • [ 56683-55-7 ]
  • C48H73NO6 [ No CAS ]
  • 8-(2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecin-15-yl)-2 ,3,6,11,12-pentakis(pentyloxy)triphenyleno[1,2-d]oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% Stage #1: 2,3-(4'-carboxybenzo)-1,4,7,10,13-pentaoxacyclopentadeca-2-ene With oxalyl dichloride; N,N-dimethyl-formamide for 0.166667h; Reflux; Inert atmosphere; Stage #2: C48H73NO6 With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 72h; Reflux; Inert atmosphere; 27 Example 27 - Method of Synthesising Compound 27 Compound 27 was synthesised using the following method. A solution of 4 -Carboxybenzo- 15-crown-5 (600 mg, 1.92 mmol), Oxalyl chloride (2.0 ml_, 23.6 mmol) and Dimethylformamide (0.01 ml, 0.129 mmol) was heated and held at reflux for 10 minutes under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. A solution of Precursor 2 (100 mg, 0.132 mmol) and N,N-Diisopropylethylamine (0.1 ml_, 0.574 mmol) in PhMe (5 ml_) was added. The reaction was then heated and held at reflux for 72 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 mins under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 10 % EtOAc: 90 % n- hexane) to afford compound 27 as a brown solid (22 mg, 17 %). The name for Compound 27 is 8-(2,3,5,6,8,9, 11 , 12- octahydrobenzo[b][1 ,4,7, 10, 13]pentaoxacyclopentadecin-15-yl)-2,3,6, 11 , 12- pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole. Compound 27 had the following characterisation data: 1 H NMR bH: (300 MHz, CDCb) 10.10 (1 H, s), 8.04-7.80 (6 H, m), 6.99 (1 H, d, 8.35), 4.53-4.38 (4 H, m), 4.33-4.17 (10 H, m), 4.06-3.90 (4 H, m), 3.89-3.73 (8 H, m), 2.10-1.88 (10 H, m), 1.69-1.44 (20 H, m), 1.07-0.92 (15 H, m) ppm. 13C NMR bC: (100 MHz, CDCb) 161.6, 152.1 , 149.6, 149.1 , 148.9, 148.4, 142.9, 140.7, 140.1 , 127.2, 124.7, 124.0, 123.6, 123.4, 121.7, 120.5, 1 16.4, 1 13.2, 1 12.9, 1 11.1 , 108.3, 107.0, 103.4, 71.3, 70.6, 70.5, 70.0, 70.0, 69.9, 69.6, 69.5, 69.2, 68.9, 68.7, 29.8, 29.4, 29.3, 29.3, 28.7, 28.5, 28.4, 22.8, 22.7, 14.3, 14.3 ppm. MALDI m/z 965.9 ([M]+ 100%).
17% Stage #1: 2,3-(4'-carboxybenzo)-1,4,7,10,13-pentaoxacyclopentadeca-2-ene With oxalyl dichloride; N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Reflux; Stage #2: C48H73NO6 With N-ethyl-N,N-diisopropylamine In toluene for 72h; Reflux; Inert atmosphere; Method of Synthesising Compound 27 Compound 27 was synthesised using the following method. A solution of 4'-Carboxybenzo-15- crown-5 (600 mg, 1.92 mmol), Oxalyl chloride (2.0 mL, 23.6 mmol) and Dimethylformamide (0.01 ml, 0.129 mmol) was heated and held at reflux for 10 minutes under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. A solution of Precursor 2 (100 mg, 0.132 mmol) and N,N-Diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was added. The reaction was then heated and held at reflux for 72 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 mins under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 10 % EtOAc: 90 % n-hexane) to afford compound 27 as a brown solid (22 mg, 17 %). The name for Compound 27 is 8-(2,3,5,6,8,9, 11,12- octahydrobenzo[b][1 ,4,7,10,13]pentaoxacyclopentadecin-15-yl)-2,3,6,11,12- pentakis(pentyloxy)triphenyleno[1,2-d]oxazole. Compound 27 had the following characterisation data: 1H NMR δH: (300 MHz, CDCI3) 10.10 (1 H, s), 8.04 - 7.80 (6 H, m), 6.99 (1 H, d, J 8.35 Hz), 4.53 - 4.38 (4H, m), 4.33 - 4.17 (10H, m), 4.06 - 3.90 (4H, m), 3.89 - 3.73 (8H, m), 2.10 - 1.88 (10H, m), 1.69 - 1.44 (20H, m), 1.07 0.92 (15H, m) ppm. 13C NMR δc: (100 MHz, CDCI3) 161.6, 152.1, 149.6, 149.1 , 148.9, 148.4, 142.9, 140.7, 140.1 , 127.2, 124.7, 124.0, 123.6, 123.4, 121.7, 120.5, 116.4, 113.2, 112.9, 111.1 , 108.3, 107.0, 103.4, 71.3, 70.6, 70.5, 70.0, 70.0, 69.9, 69.6, 69.5, 69.2, 68.9, 68.7, 29.8, 29.4, 29.3, 29.2, 28.7, 28.5, 28.4, 22.8, 22.7, 14.4, 14.3 ppm. MALDI m/z. 965.9 ([M]+ 100%).
17% Stage #1: 2,3-(4'-carboxybenzo)-1,4,7,10,13-pentaoxacyclopentadeca-2-ene With oxalyl dichloride; N,N-dimethyl-formamide for 0.166667h; Reflux; Inert atmosphere; Stage #2: C48H73NO6 With N-ethyl-N,N-diisopropylamine In toluene for 72h; Reflux; Inert atmosphere; Method of Synthesising Compound 27 Compound 27 was synthesised using the following method. A solution of 4'-Carboxybenzo-15- crown-5 (600 mg, 1.92 mmol), Oxalyl chloride (2.0 mL, 23.6 mmol) and Dimethylformamide (0.01 ml, 0.129 mmol) was heated and held at reflux for 10 minutes under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. A solution of Precursor 2 (100 mg, 0.132 mmol) and N,N-Diisopropylethylamine (0.1 mL, 0.574 mmol) in PhMe (5 mL) was added. The reaction was then heated and held at reflux for 72 h under N2. The reaction was cooled to room temperature and then evaporated to dryness in vacuo. The solid was then heated and held at 240 °C for 15 mins under N2. The crude black solid was then cooled to room temperature and purified via flash column chromatography (silica, 10 % EtOAc: 90 % n-hexane) to afford compound 27 as a brown solid (22 mg, 17 %). The name for Compound 27 is 8-(2,3,5,6,8,9, 11,12- octahydrobenzo[b][1 ,4,7,10,13]pentaoxacyclopentadecin-15-yl)-2,3,6,11,12- pentakis(pentyloxy)triphenyleno[1 ,2-d]oxazole. Compound 27 had the following characterisation data: 1H NMR 6H: (300 MHz, CDCh) 10.10 (1 H, s), 8.04 - 7.80 (6 H, m), 6.99 (1 H, d, J 8.35 Hz), 4.53 - 4.38 (4H, m), 4.33 - 4.17 (10H, m), 4.06 - 3.90 (4H, m), 3.89 - 3.73 (8H, m), 2.10 - 1.88 (10H, m), 1.69 - 1.44 (20H, m), 1.07 0.92 (15H, m) ppm. 13C NMR 6c: (100 MHz, CDCh) 161.6, 152.1 , 149.6, 149.1 , 148.9, 148.4, 142.9, 140.7, 140.1 , 127.2, 124.7, 124.0, 123.6, 123.4, 121.7, 120.5, 116.4, 113.2, 112.9, 111.1, 108.3, 107.0, 103.4, 71.3, 70.6, 70.5, 70.0, 70.0, 69.9, 69.6, 69.5, 69.2, 68.9, 68.7, 29.8, 29.4, 29.3, 29.2, 28.7, 28.5, 28.4, 22.8, 22.7, 14.4, 14.3 ppm. MALDI m/z: 965.9 ([M]+ 100%).
  • 50
  • [ 56683-55-7 ]
  • Na2[Mo6I8(MeO)6] [ No CAS ]
  • 2Na(1+)*C90H114I8Mo6O42(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In dimethyl sulfoxide at 90℃; for 18h; Inert atmosphere;
  • 51
  • [ 56683-55-7 ]
  • [ 1003863-35-1 ]
  • N-((2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl)-2,3,5,6,8,9,11,12-octahydrobenzo[b][1,4,7,10,13]pentaoxacyclopentadecine-15-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 2,3-(4'-carboxybenzo)-1,4,7,10,13-pentaoxacyclopentadeca-2-ene With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 2-(azidomethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine With tributylphosphine In tetrahydrofuran at 0 - 20℃; for 3h;
  • 52
  • [ 56683-55-7 ]
  • [ 132139-11-8 ]
  • C36H54N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;
Same Skeleton Products
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