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Chemistry
Organic Building Blocks
Aryls
benzo-crown-ether
Dibenzo-24-crown-8
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benzo-crown-ether

[ CAS No. 14174-09-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 14174-09-5
Chemical Structure| 14174-09-5
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Product Details of [ 14174-09-5 ]

CAS No. :14174-09-5 MDL No. :MFCD00005101
Formula : C24H32O8 Boiling Point : -
Linear Structure Formula :- InChI Key :UNTITLLXXOKDTB-UHFFFAOYSA-N
M.W : 448.51 Pubchem ID :84238
Synonyms :

Safety of [ 14174-09-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14174-09-5 ]

* 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 [ 14174-09-5 ]

[ 14174-09-5 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 14174-09-5 ]
  • [ 17455-23-1 ]
Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1688 - 1695
  • 2
  • [ 14174-09-5 ]
  • 2-[(Anthracen-9-ylmethyl)-amino]-ethanethiol; hydrobromide [ No CAS ]
  • C34H32N2S2*2C24H32O8*2H(1+)*2I3(1-) [ No CAS ]
Reference： [1]Chemical Communications,1998,p. 1437 - 1438
  • 3
  • [ 14174-09-5 ]
  • [ 142-64-3 ]
  • C24H32O8*C4H10N2*2ClH [ No CAS ]
Reference： [1]Journal of Solution Chemistry,1998,vol. 27,p. 755 - 759
  • 4
  • C24H32O8*C4H10N2*2ClH [ No CAS ]
  • [ 14174-09-5 ]
  • [ 142-64-3 ]
Reference： [1]Journal of Solution Chemistry,1998,vol. 27,p. 755 - 759
  • 5
  • [ 14174-09-5 ]
  • [ 24424-99-5 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C24H32O8*C22H29NO3*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Chemistry Letters,1999,p. 1015 - 1016
  • 6
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C12H19NO*F6P(1-)*H(1+) [ No CAS ]
  • C24H32O8*C21H27NO2*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Chemistry Letters,1999,p. 1015 - 1016
[2]Journal of Organic Chemistry,2006,vol. 71,p. 5093 - 5104
  • 7
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C26H29NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5093 - 5104
[2]Chemistry Letters,1999,p. 1015 - 1016
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 1182 - 1205
  • 8
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C18H19NO*F6P(1-)*H(1+) [ No CAS ]
  • C27H27NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Chemistry Letters,1999,p. 1015 - 1016
[2]Journal of Organic Chemistry,2006,vol. 71,p. 5093 - 5104
  • 9
  • [ 14174-09-5 ]
  • [ 6613-44-1 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C26H29NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5093 - 5104
[2]Chemistry Letters,1999,p. 1015 - 1016
  • 10
  • [ 14174-09-5 ]
  • [ 133415-14-2 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 4419 - 4426
[2]Chemistry - A European Journal,2016,vol. 22,p. 14264 - 14272
  • 11
  • [ 50-00-0 ]
  • [ 14174-09-5 ]
  • [ 429692-50-2 ]
Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6094 - 6104
[2]Journal of the American Chemical Society,2002,vol. 124,p. 4329 - 4335
[3]Chemical Communications,2011,vol. 47,p. 896 - 898
  • 12
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C20H28N2O2*2F6P(1-)*2H(1+) [ No CAS ]
  • C38H44N2O4*C24H32O8*2F6P(1-)*2H(1+) [ No CAS ]
  • C38H44N2O4*2C24H32O8*2F6P(1-)*2H(1+) [ No CAS ]
Reference： [1]Chemical Communications,2002,p. 2720 - 2721
  • 13
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C22H32N2O2*2F6P(1-)*2H(1+) [ No CAS ]
  • C40H48N2O4*C24H32O8*2F6P(1-)*2H(1+) [ No CAS ]
  • C40H48N2O4*2C24H32O8*2F6P(1-)*2H(1+) [ No CAS ]
Reference： [1]Chemical Communications,2002,p. 2720 - 2721
  • 14
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C24H28N2O2*2F6P(1-)*2H(1+) [ No CAS ]
  • C42H44N2O4*2C24H32O8*2F6P(1-)*2H(1+) [ No CAS ]
  • C42H44N2O4*C24H32O8*2F6P(1-)*2H(1+) [ No CAS ]
Reference： [1]Chemical Communications,2002,p. 2720 - 2721
  • 15
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C34H58N4O2*4F6P(1-)*4H(1+) [ No CAS ]
  • C52H74N4O4*4C24H32O8*4F6P(1-)*4H(1+) [ No CAS ]
Reference： [1]Chemical Communications,2002,p. 2720 - 2721
  • 16
  • [ 14174-09-5 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • 3,5-dimethyl-thiobenzoic acid <i>S</i>-pyridin-2-yl ester [ No CAS ]
  • C26H29NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Chemistry Letters,2002,p. 924 - 925
  • 17
  • [ 14174-09-5 ]
  • [ 603-35-0 ]
  • 4-tert-butylbenzyl-4'-bromomethylbenzylammonium hexafluorophosphate [ No CAS ]
  • [2]-{(N-4-tert-butylbenzyl)-N-{4-[(triphenylphosphonio)methyl]benzyl}ammonium}(dibenzo[24]crown-8)rotaxane} bis(hexafluorophosphate) [ No CAS ]
Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 5170 - 5183
  • 18
  • [ 14174-09-5 ]
  • [ 603-35-0 ]
  • Bis(4-bromomethylbenzyl)ammonium hexafluorophosphate [ No CAS ]
  • C52H47NP2(2+)*3F6P(1-)*H(1+) [ No CAS ]
  • [2]-{bis{4-[(triphenylphosphonio)methyl]benzyl}ammonium}(dibenzo[24]crown-8)rotaxane} tris(hexafluorophosphate) [ No CAS ]
Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 5170 - 5183
[2]Organic Letters,1999,vol. 1,p. 129 - 132
  • 19
  • [ 14174-09-5 ]
  • [ 198695-69-1 ]
Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 2547 - 2558
  • 20
  • [ 14174-09-5 ]
  • (E)-N-(4-tert-butylbenzyl)-4-(1-methyl-2-phenylvinyl)benzylammonium hexafluorophosphate [ No CAS ]
  • [2]-[(Z)-N-(4-tert-butylbenzyl)-4-(1-methyl-2-phenylvinyl)benzylammonium]-(dibenzo[24]crown-8)}rotaxane hexafluorophosphate [ No CAS ]
Reference： [1]Chemical Communications,2003,p. 2250 - 2251
[2]Journal of Organic Chemistry,2009,vol. 74,p. 2374 - 2379
  • 21
  • [ 14174-09-5 ]
  • [ 1493-13-6 ]
  • [ 25569-79-3 ]
  • 2-[(2,2'-dimethoxy-[1,1']binaphthalenyl-3-ylmethyl)-amino]-ethanol [ No CAS ]
  • C34H33NO4*C24H32O8*CHF3O3S [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 3438 - 3439
  • 22
  • [ 14174-09-5 ]
  • C36H43NS*F6P(1-)*H(1+) [ No CAS ]
  • C36H43NS*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Chemistry Letters,2004,vol. 33,p. 52 - 53
  • 23
  • [ 14174-09-5 ]
  • [ 54132-75-1 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C26H30N2O2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% A mixture of sec-ammonium salt S6 (2.0 g, 5.0 mmol) and <strong>[14174-09-5]dibenzo-24-crown-8</strong>-ether (DB24C8) (2.5 g, 5.5 mmol) in CHCl3 (7.0 mL) was stirred for 10 min at room temperature. To the solution was added 3,5-dimethylphenyisocyanate (1.4 mL, 10 mmol) and DBTDL (47 muL, 50 mumol) as catalyst at the same temperature. The reaction mixture was stirred for 24 h and poured into diethyl ether and the precipitates were collected by decantation. The residue was purified by silica gel column chromatography (eluent: CHCl3 / CH3CN = 100/5, Rf = 0.4) to give ure-Rot·PF6 (3.2 g, 3.2 mmol, 64%) as a white solid. m.p. 158.0-160.0 C; 1H NMR (400 MHz, CDCl3, 298 K) delta 7.56 (s, 1H, NH), 7.35 (d, J = 8.0 Hz, 2H), 7.29 (d, J = 8.0 Hz, 2H), 7.27 (s, 2H), 7.11 (s, 2H), 6.91 - 6.88 (m, 4H), 6.85 (s, 1H), 6.81 - 6.78 (m, 4H), 6.68 (s, 1H), 5.09 (s, 2H), 4.60 (t, 2H), 4.42 (t, 2H), 4.09 (s, 8H), 3.75 (s, 8H), 3.42 (s, 8H), 2.27 (s, 6H), 2.15 (s, 6H) ppm; 13C NMR (100 MHz, CDCl3, 298 K) delta 147.5, 138.6, 138.3, 137.8, 131.4, 131.3, 130.6, 129.6, 128.1, 126.6, 125.1, 121.7, 116.9, 112.7, 70.6, 70.1, 68.2, 65.7, 52.6, 52.3, 21.4, 21.2 ppm; IR (KBr) nu 3394, 3156, 2919, 1731, 1613, 1550, 1505, 1454, 1253, 1216, 1124, 1057, 954, 843, 747, 557 cm-1; FAB HR-MS Calc?d for [M-PF6]+: m/z = 851.4478; found: m/z = 851.4486.
Reference： [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 179 - 185
[2]Chemistry Letters,2016,vol. 45,p. 445 - 447
  • 24
  • [ 14174-09-5 ]
  • [ 54132-75-1 ]
  • N-3,5-di-tert-butylbenzyl-N-3-hydroxypropylammonium hexafluorophosphate [ No CAS ]
  • C27H40N2O2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 179 - 185
  • 25
  • [ 14174-09-5 ]
  • N-3,5-di-tert-butylbenzyl-N-3-hydroxypropylammonium hexafluorophosphate [ No CAS ]
  • [ 822-06-0 ]
  • C44H74N4O4*2C24H32O8*2F6P(1-)*2H(1+) [ No CAS ]
Reference： [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 179 - 185
  • 26
  • [ 14174-09-5 ]
  • [ 22201-45-2 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C28H33NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2004,vol. 6,p. 4507 - 4509
  • 27
  • [ 14174-09-5 ]
  • [ 1538-75-6 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C24H32O8*C22H29NO2*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5093 - 5104
[2]Organic Letters,2004,vol. 6,p. 4507 - 4509
  • 28
  • [ 14174-09-5 ]
  • [ 122-52-1 ]
  • N-(4-azidomethylbenzyl)-4-tert-butylbenzylammonium hexafluorophosphate [ No CAS ]
  • C24H32O8*C23H35N2O3P*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2004,vol. 6,p. 4183 - 4186
  • 29
  • C19H23NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C28H31NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2005,vol. 7,p. 1199 - 1202
  • 30
  • C26H29NO2*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C35H37NO3*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2005,vol. 7,p. 1199 - 1202
  • 31
  • C35H53NO4*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • C39H53NO3*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2005,vol. 7,p. 1199 - 1202
  • 32
  • C25H25NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 766-77-8 ]
  • C33H37NOSi*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3851 - 3853
  • 33
  • [ 499-06-9 ]
  • [ 14174-09-5 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C26H29NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Chemistry Letters,2007,vol. 36,p. 102 - 103
  • 34
  • [ 14174-09-5 ]
  • [ 81-23-2 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C41H53NO5*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Chemistry Letters,2007,vol. 36,p. 102 - 103
  • 35
  • [ 14174-09-5 ]
  • [ 855124-86-6 ]
Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 224 - 231
[2]Chemical Communications,2015,vol. 51,p. 1089 - 1091
  • 36
  • (+/-)-(Z)-N-(4-tert-butylbenzyl)-5-(cis-2-ethenylcyclopropyl)pent-4-en-1-ylammonium hexafluorophosphate [ No CAS ]
  • [ 14174-09-5 ]
  • C24H32O8*C21H31N*H(1+)*PF6(1-) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 3500 - 3501
  • 37
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 86-74-8 ]
  • C24H32O8*C31H28N2*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4995 - 4998
  • 38
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 99-52-5 ]
  • C24H32O8*C26H27N3O2*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4995 - 4998
  • 39
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 42122-73-6 ]
  • C24H32O8*C31H34N2O4*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4995 - 4998
  • 40
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 70-55-3 ]
  • C24H32O8*C26H28N2O2S*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4995 - 4998
  • 41
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 73258-94-3 ]
  • C24H32O8*C28H30N2O*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4995 - 4998
  • 42
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 1193-55-1 ]
  • [ 14174-09-5 ]
  • C24H32O8*C26H29NO2*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4995 - 4998
  • 43
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 72898-42-1 ]
  • C24H32O8*C34H31NS*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4995 - 4998
  • 44
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
  • [ 4559-70-0 ]
  • C24H32O8*C31H30NOP*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4995 - 4998
  • 45
  • [ 14174-09-5 ]
  • [ 603-35-0 ]
  • 4-tert-butylbenzyl-4'-bromomethylbenzylammonium hexafluorophosphate [ No CAS ]
  • C37H39NP(1+)*H(1+)*2F6P(1-) [ No CAS ]
  • [2]-{(N-4-tert-butylbenzyl)-N-{4-[(triphenylphosphonio)methyl]benzyl}ammonium}(dibenzo[24]crown-8)rotaxane} bis(hexafluorophosphate) [ No CAS ]
Reference： [1]Organic Letters,1999,vol. 1,p. 129 - 132
  • 46
  • N-[2-(3,3,3-triphenylpropionyloxy)ethyl]-N-[2-(10-undecenoyloxy)ethyl]ammonium hexafluorophosphate [ No CAS ]
  • [ 14174-09-5 ]
  • 2C24H32O8*C70H86N2O8*2F6P(1-)*2H(1+) [ No CAS ]
Reference： [1]Chemistry Letters,2007,vol. 36,p. 1196 - 1197
  • 47
  • [ 14174-09-5 ]
  • [ 13510-35-5 ]
  • [ 284467-38-5 ]
Reference： [1]Inorganica Chimica Acta,2000,vol. 300-302,p. 1004 - 1013
  • 48
  • [ 14174-09-5 ]
  • C51H45N3O3*3F6P(1-)*3H(1+) [ No CAS ]
  • [ 479-27-6 ]
  • 3C24H32O8*C81H69N9*3F6P(1-)*3H(1+) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 4436 - 4439
  • 49
  • [ 14174-09-5 ]
  • C16H27NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 121238-27-5 ]
  • C24H32O8*C30H45NO10*F6P(1-)*H(1+) [ No CAS ]
  • C24H32O8*C30H45NO10*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2008,vol. 10,p. 753 - 756
  • 50
  • [ 67950-78-1 ]
  • [ 14174-09-5 ]
  • C28H32N2O*2F6P(1-)*2H(1+) [ No CAS ]
  • [ 93-97-0 ]
  • C18H28O7*C24H32O8*C35H36N2O2*2F6P(1-)*2H(1+) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 13852 - 13853
  • 51
  • [ 14174-09-5 ]
  • N-neopentyl-N-(4-hydroxymethylbenzyl)ammonium hexafluorophosphate [ No CAS ]
  • [ 25569-79-3 ]
  • C22H29NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9245 - 9250
  • 52
  • [ 14174-09-5 ]
  • C22H29NO4*F6P(1-)*H(1+) [ No CAS ]
  • [ 25569-79-3 ]
  • C24H32O8*C31H37NO5*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9245 - 9250
  • 53
  • [ 14174-09-5 ]
  • N-cyclohexylmethyl-N-(4-hydroxymethylbenzyl)ammonium hexafluorophosphate [ No CAS ]
  • [ 25569-79-3 ]
  • C24H31NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9245 - 9250
  • 54
  • [ 14174-09-5 ]
  • [ 27151-66-2 ]
  • C17H21NO*F6P(1-)*H(1+) [ No CAS ]
  • C24H32O8*C25H33NO4*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 9245 - 9250
  • 55
  • [ 14174-09-5 ]
  • N-(3,5-dimethylbenzyl)-4-(1-methyl-2-phenylvinyl)benzylammonium hexafluorophosphate [ No CAS ]
  • [2]-{(dibenzo[24]crown-8)-[(Z)-N-(3,5-dimethylbenzyl)-4-(1-methyl-2-phenylvinyl)benzylammonium]rotaxane hexafluorophosphate [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 2374 - 2379
  • 56
  • [ 14174-09-5 ]
  • C18H15N*F6P(1-)*H(1+) [ No CAS ]
  • C18H15N*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2018,vol. 20,p. 1046 - 1049
[2]Tetrahedron,2009,vol. 65,p. 2824 - 2829
  • 57
  • [ 14174-09-5 ]
  • C22H35N*F6P(1-)*H(1+) [ No CAS ]
  • C26H36N5O10(1+)*F6P(1-) [ No CAS ]
  • C24H32O8*C48H71N6O10(1+)*2F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 5186 - 5190
[2]Journal of Organic Chemistry,2013,vol. 78,p. 4099 - 4106
  • 58
  • [ 14174-09-5 ]
  • C19H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 147808-02-4 ]
  • 2C24H32O8*C44H43FN2O2*2F6P(1-)*2H(1+) [ No CAS ]
Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 5497 - 5500
  • 59
  • [ 14174-09-5 ]
  • C19H23NO*F6P(1-)*H(1+) [ No CAS ]
  • 2,6-dimethoxyphenyl nitrile N-oxide [ No CAS ]
  • C24H32O8*C28H32N2O4*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2010,vol. 12,p. 3828 - 3831
  • 60
  • [ 14174-09-5 ]
  • C12H17N*F6P(1-)*H(1+) [ No CAS ]
  • 2,6-dimethoxyphenyl nitrile N-oxide [ No CAS ]
  • C21H26N2O3*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2010,vol. 12,p. 3828 - 3831
  • 61
  • C26H29NO2*C24H32O8*F6P(1-)*H(1+) [ No CAS ]
  • [ 14174-09-5 ]
Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 13783 - 13794
  • 62
  • [ 14174-09-5 ]
  • [ 18880-00-7 ]
  • 1,2-bis(4,4'-dipyridinium)ethane ditrifluoromethanesulfonate [ No CAS ]
  • 4CF3O3S(1-)*C44H50N4(4+) [ No CAS ]
  • 4CF3O3S(1-)*C24H32O8*C44H50N4(4+) [ No CAS ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1763 - 1770
  • 63
  • [ 14174-09-5 ]
  • [ 14002-33-6 ]
  • [ 1493-13-6 ]
  • [ 2923-28-6 ]
  • [ 6613-44-1 ]
  • TR-A0015 [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% Specifically, 3,3'-azanediyldipropan-1-ol (200 mg, 1.50 mmol), dibenzo-24-crown-8-ether (808 mg, 1.80 mmol), and trifluoromethanesulfonic acid (133 mL, 1.50 mmol) were placed in a two-necked eggplant-shaped flask, followed by replacement with argon and then dissolution in CH2Cl2 (1 mL). The resulting solution was cooled to 0C and was stirred. Then, 3,5-dimethylbenzoyl chloride (608 mg, 3.61 mmol), having been replaced with argon and dissolved in CH2Cl2 (2 mL), was added thereto. Furthermore, after addition of silver trifluoromethanesulfonate (926 mg, 3.61 mmol), the temperature of the resulting mixture was gradually increased from 0C to room temperature, and the mixture was successively stirred at room temperature for 27 hours. After confirmation of TLC (CHCl3/MeOH = 10/1), saturated aqueous Na2CO3 was added to quench the reaction. Organic materials were extracted from the reaction mixture with CHCl3, dried over MgSO4, and subjected to filtration. The solvent was distilled away under reduced pressure. The obtained crude product was applied to silica gel column chromatography (eluent: CHCl3/MeOH = 1/0 to 10/1) and then to recycling HPLC (eluent: CHCl3) for separation and purification to obtain a target compound.The target compound was white-foamed solid, and the amount was 142 mg and the yield was 9%. The 1H NMR spectrum (400 MHz, CDCl3, 298 K) of the obtained target compound was as follows, and it was confirmed that the obtained compound was the compound on the right side of the above-mentioned Chemical Formula 7: That is, delta 7.54 (s, 4H), 7.17 (s, 2H), 6.86 (brd, 8H), 4.18-4.17 (m, 8H), 4.12 (t, J=6.4 Hz, 4H), 3.88-3.87 (m, 8H), 3.73 (brd, 8H), 3.56-3.47 (m, 4H), 2.30 (s, 12H), 2.04-1.94 (m, 4H) (unit: ppm).
Reference： [1]Patent: EP2348021,2011,A1 .Location in patent: Page/Page column 6
  • 64
  • [ 14174-09-5 ]
  • [ 34891-25-3 ]
  • [ 1493-13-6 ]
  • [ 25569-79-3 ]
  • TR-A0010 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% That is, bis (1-pentanol)amine (190 mg, 0.65 mmol), <strong>[14174-09-5]dibenzo-24-crown-8</strong>-ether (350 mg, 0.78 mmol), and trifluoromethanesulfonic acid (58 mL, 0.65 mmol) were placed in a two-necked eggplant-shaped flask, followed by replacement with argon and then dissolution in CH2Cl2 (1.2 mL). The resulting solution was cooled to 0C and was stirred. After 12 hours, 3,5-dimethylbenzoic acid anhydride (367 mg, 1.30 mmol) was added thereto. Then, the temperature of the resulting mixture was gradually increased from 0C to room temperature, and the mixture was successively stirred at room temperature for 6 hours. After confirmation of TLC (CHCl3/MeOH = 10/1), saturated aqueous Na2CO3 was added to quench the reaction. Organic materials were extracted from the reaction mixture with CHCl3, washed with 1 M HCl aqueous brine, dried over MgSO4, and subjected to filtration. The solvent was distilled away under reduced pressure. The obtained crude product was applied to silica gel column chromatography (eluent: CHCl3/MeOH = 1/0 to 10/1) and then to recycling HPLC (eluent: CHCl3) for separation and purification to obtain a target compound.The target compound was white-foamed solid, and the amount was 388 mg and the yield was 57%. The 1H NMR spectrum (400 MHz, CDCl3, 298 K) of the obtained target compound was as follows, and it was confirmed that the obtained compound was the compound in the above-mentioned Chemical Formula 8: That is: delta 7.59 (s, ArH, 4H), 7.18 (s, ArH, 2H), 6.89-6.83 (m, ArH, 8H), 4.14 (m, CH2, 8H), 4.08 (t, J=6.4 Hz, CH2, 4H), 3.86 (m, CH2, 8H), 3.70 (m, CH2, 8H), 3.25 (m, CH2, 4H), 2.34 (s, dimethyl of end cap, CH3, 12H), 1.54-1.44 (m, CH2, 8H), 1.26-1.17 (m, CH2, 4H) (unit: ppm).
Reference： [1]Patent: EP2348021,2011,A1 .Location in patent: Page/Page column 6-7
  • 65
  • [ 14174-09-5 ]
  • C38H31N3O2*F6P(1-)*H(1+) [ No CAS ]
  • [ 195133-98-3 ]
  • C24H32O8*C53H42N6O2*F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6022 - 6026
  • 66
  • [ 14174-09-5 ]
  • C44H60N2S2*2F6P(1-)*2H(1+) [ No CAS ]
  • 2C24H32O8*C44H60N2S2*2F6P(1-)*2H(1+) [ No CAS ]
  • C24H32O8*C44H60N2S2*2F6P(1-)*2H(1+) [ No CAS ]
Reference： [1]Supramolecular Chemistry,2011,vol. 23,p. 65 - 68
[2]Supramolecular Chemistry,2011,vol. 23,p. 65 - 68
  • 67
  • [ 14174-09-5 ]
  • [ 25569-79-3 ]
  • [ 1392438-88-8 ]
  • [ 1392438-90-2 ]
Reference： [1]Organic Letters,2012,vol. 14,p. 4122 - 4125
  • 68
  • [ 14174-09-5 ]
  • C15H12N4*2ClHO4 [ No CAS ]
  • C24H32O8*C15H12N4*2ClHO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 34.84℃; General procedure: The solutions of the pseudorotaxanes were made by dilutions using volumetric glassware and pipettes. A typical experiment is as follows. Compound 1a (44.8 mg, 0.1 mmol) and <strong>[14174-09-5]dibenzo-24-crown-8</strong> (44.8 mg, 0.1 mmol) were dissolved in CD3CN (5 ml) giving a thread and crown concentration of 20 mM each, respectively. 1H NMR of this prepared clear solution was recorded immediately. The ratio for bound to unbound threads was obtained from the integration of the thread and crown peaks in the 1H NMR spectra and averaged over two experiments. The resonances for the aromatic protons of both the thread and the crown (although the methylene signal of the thread was well resolved, those of the crown were overlapped) were chosen for this purpose, since the resolution was better in this region for both the counterparts, thus minimizing errors. The association constant (Ka) was then measured.
Reference： [1]Tetrahedron,2012,vol. 68,p. 9826 - 9835,10
  • 69
  • [ 14174-09-5 ]
  • C15H12N4*2F6P(1-)*2H(1+) [ No CAS ]
  • C24H32O8*C15H12N4*2H(1+)*2F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 34.84℃; General procedure: The solutions of the pseudorotaxanes were made by dilutions using volumetric glassware and pipettes. A typical experiment is as follows. Compound 1a (44.8 mg, 0.1 mmol) and <strong>[14174-09-5]dibenzo-24-crown-8</strong> (44.8 mg, 0.1 mmol) were dissolved in CD3CN (5 ml) giving a thread and crown concentration of 20 mM each, respectively. 1H NMR of this prepared clear solution was recorded immediately. The ratio for bound to unbound threads was obtained from the integration of the thread and crown peaks in the 1H NMR spectra and averaged over two experiments. The resonances for the aromatic protons of both the thread and the crown (although the methylene signal of the thread was well resolved, those of the crown were overlapped) were chosen for this purpose, since the resolution was better in this region for both the counterparts, thus minimizing errors. The association constant (Ka) was then measured.
Reference： [1]Tetrahedron,2012,vol. 68,p. 9826 - 9835,10
  • 70
  • [ 14174-09-5 ]
  • C17H16N4*2BF4(1-)*2H(1+) [ No CAS ]
  • C24H32O8*C17H16N4*2BF4(1-)*2H(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 34.84℃; General procedure: The solutions of the pseudorotaxanes were made by dilutions using volumetric glassware and pipettes. A typical experiment is as follows. Compound 1a (44.8 mg, 0.1 mmol) and <strong>[14174-09-5]dibenzo-24-crown-8</strong> (44.8 mg, 0.1 mmol) were dissolved in CD3CN (5 ml) giving a thread and crown concentration of 20 mM each, respectively. 1H NMR of this prepared clear solution was recorded immediately. The ratio for bound to unbound threads was obtained from the integration of the thread and crown peaks in the 1H NMR spectra and averaged over two experiments. The resonances for the aromatic protons of both the thread and the crown (although the methylene signal of the thread was well resolved, those of the crown were overlapped) were chosen for this purpose, since the resolution was better in this region for both the counterparts, thus minimizing errors. The association constant (Ka) was then measured.
Reference： [1]Tetrahedron,2012,vol. 68,p. 9826 - 9835,10
  • 71
  • [ 14174-09-5 ]
  • C17H16N4*2ClHO4 [ No CAS ]
  • C24H32O8*C17H16N4*2ClHO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 34.84℃; General procedure: The solutions of the pseudorotaxanes were made by dilutions using volumetric glassware and pipettes. A typical experiment is as follows. Compound 1a (44.8 mg, 0.1 mmol) and <strong>[14174-09-5]dibenzo-24-crown-8</strong> (44.8 mg, 0.1 mmol) were dissolved in CD3CN (5 ml) giving a thread and crown concentration of 20 mM each, respectively. 1H NMR of this prepared clear solution was recorded immediately. The ratio for bound to unbound threads was obtained from the integration of the thread and crown peaks in the 1H NMR spectra and averaged over two experiments. The resonances for the aromatic protons of both the thread and the crown (although the methylene signal of the thread was well resolved, those of the crown were overlapped) were chosen for this purpose, since the resolution was better in this region for both the counterparts, thus minimizing errors. The association constant (Ka) was then measured.
Reference： [1]Tetrahedron,2012,vol. 68,p. 9826 - 9835,10
  • 72
  • [ 120-80-9 ]
  • [ 19249-03-7 ]
  • [ 14174-09-5 ]
YieldReaction ConditionsOperation in experiment
36% With potassium hexafluorophosphate; potassium carbonate; In acetonitrile; for 168h;Inert atmosphere; Reflux; Darkness; Catechol (1.01 g, 9.10 mmol), tri(ethylene glycol) ditosylate (4.16 g, 9.10 mmol) and KPF6 (6.66 g, 36.0 mmol) were dissolved in MeCN (120 mL). N2 (g) was bubbled through the solution for 20 min. The flask was wrapped in aluminum foil to exclude light, and K2CO3 (5.03 g, 36mmol) was added. The mixture was heated at reflux under N2 (g). After one week, the solution was allowed to cool to room temperature. The solvent was removed by rotary evaporation and the solid was partitioned between DCM and water (15 mL). The DCM layer was washed with water (3×15 mL), dried over Na2SO4, filtered, and the solvent was removed by rotary evaporation. The crude solid was purified by column chromatography (neutral alumina; 2:1 EtOAc:DCM, v:v). The fractions containing product were concentrated to yield a white solid (0.74 g, 36 %), mp 100-102 C; lit. mp 102-103 C19,21. 1H NMR (500 MHz, CDCl3) delta 7.01-6.96 (m, 4H), 4.24-4.20 (m, 4H), 3.80-3.76 (m, 4H), 3.73 (s, 4H). 13C NMR (101 MHz, CDCl3) delta 150.1, 123.0, 118.1, 71.2, 70.0, 69.0.
Reference： [1]Tetrahedron,2016,vol. 72,p. 396 - 399
  • 73
  • [ 120-80-9 ]
  • [ 240797-46-0 ]
  • [ 14174-09-5 ]
YieldReaction ConditionsOperation in experiment
87% With potassium hexafluorophosphate; potassium carbonate; In acetonitrile; for 72h;Inert atmosphere; Reflux; Darkness; Ditosylate 3a (2.23 g, 3.2 mmol), catechol (0.36 g, 3.2 mmol) and KPF6 (0.72 g, 3.9 mmol) were dissolved in MeCN (100 mL). Ar (g) was bubbled through the solution for 10 min. The flask was wrapped in aluminum foil to exclude light, and K2CO3 (1.78 g, 13 mmol) was added. The mixture was heated at reflux under Ar (g) for 3 days, allowed to cool to room temperature and the solids were filtered. The solvent was removed by rotary evaporation and the purple residue was partitioned between DCM and water. The organic layer was washed with 1:1:1 pyridine: HCl: H2O (10×20 mL), water (1×20 mL), 10 % (w/v) NaOH (3×20 mL) and water (1×20 mL). The purple solution turned bright red when it was washed with the pyridinium·HCl solution and back to purple again with the NaOH washings. The organic layer was dried over MgSO4 and activated carbon was added. The solution was filtered through Celite, filtered again and the solvent was removed. The residual pyridine was removed by drying under high vacuum to yield a white solid (1.27 g, 87 %), mp 100-102 C. Lit. yield 43 % (NaOH/DMSO), mp 102-103 C19,21. 1H NMR (400 MHz CDCl3, Fig. S10) delta 6.88 (m, 8H), 4.15 (t, J=4 Hz, 8H), 3.92 (t, J=4 Hz, 8H), 3.83 (s, 8H). 13C NMR (101 MHz, CDCl3) delta 149.1, 121.5, 114.2, 71.4, 70.1, 69.5 ESITOF: (M+H)+ m/z 449.2171 (found), 449.2174 (calculated for C24H32O8), error 0.3 ppm.
Reference： [1]Tetrahedron,2016,vol. 72,p. 396 - 399
  • 74
  • [ 14174-09-5 ]
  • C17H19NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 118727-34-7 ]
  • C75H78N6*3C24H32O8*3H(1+)*3F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% To the solution of aldehyde 11) (500 mg, 1.25 mmol) and DB24C8 (700 mg, 1.56 mmol) in dichloroethane (10 ml) was added 1,3,5-tris-(4-aminophenyl)benzene 2) (110 mg, 0.31 mmol) at rt, and the mixture was heated at 80 C for 19 h. After cooling with ice bath, to the mixture was added NaBH4 (240 mg, 6.26 mmol) and EtOH (5 ml), and then the mixture was stirred for 22 h at rt. To the mixture was added dil. HCl (aq.) and THF (5 ml), stirred for 30 min, and was neutralized with Na2CO3 (aq). After the evaporation of organic solvents, to the residue was added CHCl3, washed with water and sat. NaCl, dried over MgSO4, and concentrated. The residual solid was washed with MeOH. The suspension of the solid, aldehyde 1 (500 mg, 1.25 mmol), and DB24C8 (700 mg, 1.56 mmol) in dichloroethane (5 ml) was heated at 80 C for 12 h. After cooling with ice bath, to the mixture was added NaBH4 (120 mg, 3.13 mmol) and EtOH (2.5 ml), stirred for 20 h, and worked up as described above. The crude product was suspended in acetone (12 ml) and water (3 ml), and treated with NH4PF6 (350 mg, 2.15 mmol). After the evaporation of the solvent, the residue was collected by filtration, washed with water, and dried. The solid was chromatographed twice (the first: MH-silica gel (Fuji Silysia Chemical Chromatorex NH DM1020, eluent toluene : THF, 3 :1, the second silica gel (Kanto Chemical silica gel 60N) CH2Cl2 : THF, 15 :1) to afford the crude product. A suspension of the crude product in acetone (10 ml) and H2O (1 ml) was treated with NH4PF6 (200 mg, 1.23 mmol), and stirred 1 h. After the organic solvent had been evaporated, the resulting solid was washed with H2O to give [4]Rotaxane 2-H3X3 as a solid (462 mg, 52%).
Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 1120 - 1123
  • 75
  • C60H87N7O4(2+)*2F6P(1-)*C24H32O8 [ No CAS ]
  • [ 14174-09-5 ]
  • [ 1138-52-9 ]
  • C32H43N7O2(2+)*2F6P(1-) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 5652 - 5658
  • 76
  • [ 14174-09-5 ]
  • [ 2423-71-4 ]
  • C17H27NO2*F6P(1-)*H(1+) [ No CAS ]
  • C25H34N2O4*F6P(1-)*C24H32O8*H(1+) [ No CAS ]
Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 8835 - 8847
  • 77
  • [ 14174-09-5 ]
  • C20H23NO*F6P(1-)*H(1+) [ No CAS ]
  • 2,6-dimethoxyphenyl nitrile N-oxide [ No CAS ]
  • C29H32N2O4*F6P(1-)*H(1+)*C24H32O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% DB24C8 (1.5 g, 3.4 mmol) and sec-ammonium salt S3 (1.6 g, 3.6 mmol) was mixed in CHCl3 (8.0 mL) for 10 min. 2,6-dimethoxyphenyl nitrile N-oxide (0.79 g, 4.4 mmol) was added and stirred at room temperature for 12 h. After the solvent was removed by evaporation, white solid (2.3 g, 2.2 mmol, 65%) was obtained by silica gel column chromatography (eluent: CHCl3/CH3CN = 100/8, Rf = 0.5). m.p. 85.8-87.5 C; 1H NMR (400 MHz, 298 K, CDCl3) delta 7.48 (s, 2H, NH2), 7.37-7.33 (m, 3H), 7.26-7.24 (m, 4H), 6.88 (m, 4H), 6.84 (s, 1H), 6.79 (m, 4H), 6.65 (s, 1H), 6.63 (s, 1H), 6.42 (s, 1H), 4.65 (m, 2H), 4.64 (s, 2H), 4.57 (s, 2H), 4.43 (m, 2H), 4.10 (m, 8H), 3.79 (s, 6H), 3.78 (m, 8H), 3.46 (m, 8H), 2.14 (s, 6H); 13C NMR (100 MHz, CDCl3, 298 K) delta 167.4, 158.6, 157.0, 147.4, 138.8, 138.3, 131.3, 131.2, 131.1, 130.6, 129.4, 127.9, 126.6, 121.7, 112.6, 106.2, 104.0, 72.0, 70.6, 70.1, 68.2, 62.9, 56.0, 52.6, 52.3, 21.1 ppm; IR (KBr) nu 3154, 2917, 1594, 1505, 1477, 1254, 1112, 1057, 953, 842, 747, 557 cm-1; FAB HR-MS Calc?d for [M-PF6]+: m/z = 921.4532; found: m/z = 921.4535.
Reference： [1]Chemistry Letters,2016,vol. 45,p. 445 - 447
  • 78
  • [ 14174-09-5 ]
  • [ 31645-34-8 ]
  • [NH2(CH2C6H4-4-OCH2CH2CH=CH2)2]BARF [ No CAS ]
  • C24H32O8*C54H47NO5*C32H12BF24(1-)*H(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 24h;Reflux; [NH2(CH2C6H4-4-O(CH2)2CH=CH2)2]BARF (120 mg, 0.10 mmol), DB24C8(46 mg, 0.10 mmol) and CH2=CHCOOCH2An (106 mg, 0.40 mmol) were dissolved toCH2Cl2 (1.0 mL) and Grubbs 2nd generation catalyst (10 mg, 12 mumol) was added to thissolution. The reaction mixture was refluxed for 24 h and solvent was evaporated toyield crude product, which was purified by silicagel column chromatography (eluent:hexane/ethylacetate = 2/1 to 0/1) and preparative HPLC (eluent: CHCl3) to yield[1-H2(DB24C8)]BARF as brown oil (173 mg, 0.082 mmol, 82%)
Reference： [1]Chemistry Letters,2016,vol. 45,p. 834 - 836
  • 79
  • [ 14174-09-5 ]
  • [ 64-17-5 ]
  • 6,13-bis(methoxymethylidene)-1,4,8,11-tetraazacyclotetradeca-4,6,11,14-tetraene-κ4N(1,4,8,11)nickel(II) bis(hexafluorophosphate) [ No CAS ]
  • [ 107-15-3 ]
  • 3C24H32O8*8F6P(1-)*C56H80N24Ni4(8+)*6H2O*C2H6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% General procedure: Methylated complex 2Ni or 2Cu (0.20 g, 0.32 mmol) andethylenediamine (0.021 ml, 0.32 mmol), each dissolvedseparately in dry MeCN (20 ml), were added dropwise(syringe pump, 0.1 ml/min) to a stirred solution of <strong>[14174-09-5]dibenzo-24-crown-8</strong> (0.28 g, 0.64 mmol) in MeCN (10 ml). After12 h the reaction mixture was treated with water (100 ml)acidified with acetic acid (1 ml). The resulting mixturewas applied on a reverse-phase column (Merck silica gel60 silanized) and eluted with MeCN-H2O, 2:3, to whichammonium hexafluorophosphate (3 g/100 ml) had beenadded. The reaction products were collected as a numberof colored fractions that after partial evaporation gave either yellow (nickel complexes) or red (copper complexes) precipitates. The solids were filtered off,washed with cold water, and dried in vacuo.
Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 87 - 91
    Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 87 - 91,5
  • 80
  • [ 14174-09-5 ]
  • 6,13-bis(methoxymethylidene)-1,4,8,11-tetraazacyclotetradeca-4,6,11,14-tetraene-κ4N(1,4,8,11)nickel(II) bis(hexafluorophosphate) [ No CAS ]
  • [ 107-15-3 ]
  • 2C24H32O8*8F6P(1-)*C56H80N24Ni4(8+)*9H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% General procedure: Methylated complex 2Ni or 2Cu (0.20 g, 0.32 mmol) andethylenediamine (0.021 ml, 0.32 mmol), each dissolvedseparately in dry MeCN (20 ml), were added dropwise(syringe pump, 0.1 ml/min) to a stirred solution of <strong>[14174-09-5]dibenzo-24-crown-8</strong> (0.28 g, 0.64 mmol) in MeCN (10 ml). After12 h the reaction mixture was treated with water (100 ml)acidified with acetic acid (1 ml). The resulting mixturewas applied on a reverse-phase column (Merck silica gel60 silanized) and eluted with MeCN-H2O, 2:3, to whichammonium hexafluorophosphate (3 g/100 ml) had beenadded. The reaction products were collected as a numberof colored fractions that after partial evaporation gave either yellow (nickel complexes) or red (copper complexes) precipitates. The solids were filtered off,washed with cold water, and dried in vacuo.
Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 87 - 91
    Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 87 - 91,5
  • 81
  • [ 14174-09-5 ]
  • 6,13-bis(methoxymethylidene)-1,4,8,11-tetraazacyclotetradeca-4,6,11,14-tetraene-κ4N(1,4,8,11)nickel(II) bis(hexafluorophosphate) [ No CAS ]
  • [ 107-15-3 ]
  • 4C24H32O8*8F6P(1-)*C56H80N24Ni4(8+)*6H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% General procedure: Methylated complex 2Ni or 2Cu (0.20 g, 0.32 mmol) andethylenediamine (0.021 ml, 0.32 mmol), each dissolvedseparately in dry MeCN (20 ml), were added dropwise(syringe pump, 0.1 ml/min) to a stirred solution of <strong>[14174-09-5]dibenzo-24-crown-8</strong> (0.28 g, 0.64 mmol) in MeCN (10 ml). After12 h the reaction mixture was treated with water (100 ml)acidified with acetic acid (1 ml). The resulting mixturewas applied on a reverse-phase column (Merck silica gel60 silanized) and eluted with MeCN-H2O, 2:3, to whichammonium hexafluorophosphate (3 g/100 ml) had beenadded. The reaction products were collected as a numberof colored fractions that after partial evaporation gave either yellow (nickel complexes) or red (copper complexes) precipitates. The solids were filtered off,washed with cold water, and dried in vacuo.
Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 87 - 91
    Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 87 - 91,5
  • 82
  • [ 14174-09-5 ]
  • 6,13-bis(methoxymethylidene)-1,4,8,11-tetraazacyclotetradeca-4,6,11,14-tetraene-κ4N(1,4,8,11)nickel(II) bis(hexafluorophosphate) [ No CAS ]
  • [ 107-15-3 ]
  • C42H60N18Ni3(6+)*C24H32O8*6F6P(1-)*3H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% General procedure: Methylated complex 2Ni or 2Cu (0.20 g, 0.32 mmol) andethylenediamine (0.021 ml, 0.32 mmol), each dissolvedseparately in dry MeCN (20 ml), were added dropwise(syringe pump, 0.1 ml/min) to a stirred solution of <strong>[14174-09-5]dibenzo-24-crown-8</strong> (0.28 g, 0.64 mmol) in MeCN (10 ml). After12 h the reaction mixture was treated with water (100 ml)acidified with acetic acid (1 ml). The resulting mixturewas applied on a reverse-phase column (Merck silica gel60 silanized) and eluted with MeCN-H2O, 2:3, to whichammonium hexafluorophosphate (3 g/100 ml) had beenadded. The reaction products were collected as a numberof colored fractions that after partial evaporation gave either yellow (nickel complexes) or red (copper complexes) precipitates. The solids were filtered off,washed with cold water, and dried in vacuo.
Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 87 - 91
    Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 87 - 91,5
  • 83
  • [ 14174-09-5 ]
  • [6,13-bis-(methoxymethylidene)-1,4,8,11-tetraazacyclotetradeca-4,7,11,14-tetraene-ĸ4N1,4,8,11]copper(II)bis(hexafluorophosphate) [ No CAS ]
  • [ 107-15-3 ]
  • 2C24H32O8*8F6P(1-)*C56H80Cu4N24(8+)*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% General procedure: Methylated complex 2Ni or 2Cu (0.20 g, 0.32 mmol) andethylenediamine (0.021 ml, 0.32 mmol), each dissolvedseparately in dry MeCN (20 ml), were added dropwise(syringe pump, 0.1 ml/min) to a stirred solution of <strong>[14174-09-5]dibenzo-24-crown-8</strong> (0.28 g, 0.64 mmol) in MeCN (10 ml). After12 h the reaction mixture was treated with water (100 ml)acidified with acetic acid (1 ml). The resulting mixturewas applied on a reverse-phase column (Merck silica gel60 silanized) and eluted with MeCN-H2O, 2:3, to whichammonium hexafluorophosphate (3 g/100 ml) had beenadded. The reaction products were collected as a numberof colored fractions that after partial evaporation gave either yellow (nickel complexes) or red (copper complexes) precipitates. The solids were filtered off,washed with cold water, and dried in vacuo.
Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 87 - 91
    Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 87 - 91,5
  • 84
  • [ 14174-09-5 ]
  • [ 1047646-66-1 ]
  • C25H21NO*F6P(1-)*H(1+) [ No CAS ]
  • [ 74-88-4 ]
  • C24H32O8*C41H47N4O(1+)*2F6P(1-)*H(1+) [ No CAS ]
Reference： [1]Organic Letters,2017,vol. 19,p. 2945 - 2948
  • 85
  • [ 14174-09-5 ]
  • N-(3,5-dimethylbenzyl)-N-(12’-hydroxydodecyl)ammonium hexafluorophosphate [ No CAS ]
  • C17H18O4 [ No CAS ]
  • C38H53NO4*F6P(1-)*C24H32O8*H(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With tributylphosphine; In dichloromethane; at 20℃; for 12h; 92 mg (0.30 mmol) of carboxylic acid-containing naphthaldehyde B was dissolved in 0.50 mL of dehydrated dichloromethane and stirred for 30 minutes.Also, the axial component 1-0 0.12 g (0.25 mmol) DB 24 C 8 was added to 0.5 mL of a dehydrated dichloromethane solution of 0.10 g (0.22 mmol), and the mixture was stirred at room temperature.These were mixed, 39 muL of tributylphosphine was further added, and the mixture was stirred at room temperature for 12 hours.The reaction solution was reprecipitated with hexane: diethyl ether (= 1: 1) and purified by preparative GPC to obtain 0.26 g (yield: 47%) of aldehyde 3-1.
Reference： [1]Patent: JP2017/160164,2017,A .Location in patent: Paragraph 0108-0111
  • 86
  • [ 14174-09-5 ]
  • N-(3,5-dimethylbenzyl)-N-(12’-hydroxydodecyl)ammonium hexafluorophosphate [ No CAS ]
  • C22H25NO7 [ No CAS ]
  • C43H60N2O7*F6P(1-)*C24H32O8*H(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With tributylphosphine; diisopropyl-carbodiimide; In dichloromethane; at 20℃; for 12h; 0.30 g (0.72 mmol) of nitroalkane 1-2 was dissolved in 0.5 mL of dehydrated dichloromethane and stirred for 30 minutes (solution 1).Axial component 1-0 0.5 mL of a dehydrated dichloromethane solution containing 0.19 g (0.48 mmol)0.38 g (0.58 mmol) DB 24 C 8 was added,And the mixture was stirred at room temperature.Further, 78 muL of tributylphosphine and solution 1 were added, and the mixture was stirred at room temperature for 12 hours. Purification by preparative GPC gave 0.40 g (yield: 47%) of nitroalkane [2] rotaxane 2-1.
Reference： [1]Patent: JP2017/160164,2017,A .Location in patent: Paragraph 0101; 0104
  • 87
  • [ 86-93-1 ]
  • [ 14174-09-5 ]
  • [Cs(dibenzo-24-crown-8)(1-phenyl-tetrazole-5-thiolate)] [ No CAS ]
  • [Cs2(dibenzo-24-crown-8)3(1-phenyl-tetrazole-5-thiolate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% General procedure: LiOH (0.068 g, 2.81 mmol) was added to a solution of 1-phenyl-1-H-tetrazole-5-thione (1) (0.50 g, 2.81 mmol) in methanol (40 mL) at ambient temperature. The solution was stirred for 2 h and then 15-crown-5 ether (1,4,7,10,13-Pentaoxacyclopentadecane) (0.62 g, 2.81 mmol) was added. The reaction mixture was stirred for 5 h and the volume of the solution was reduced and allowed to crystallize. Yield: 88%. 2.2.7 [Cs(<strong>[14174-09-5]dibenzo-24-crown-8</strong>)(SCN4Ph)] (8) Compound 8 was prepared using the same procedure outlined for 2 starting from 1 (0.25 g, 1.40 mmol), CsOH (0.21 g, 1.40 mmol) and <strong>[14174-09-5]dibenzo-24-crown-8</strong> (2,3,14,15-dibenzo-1,4,7,10,13,16,19,22-octaoxacyclotetracosa-2,14-diene) (0.62 g, 1.40 mmol). Yield: 93% (0.99 g, 1.30 mmol). Mp: 127-129 C (dec). 1H NMR (300 MHz, CDCl3, 25 C): delta 3.73, 3.88, 4.12 (m, 24 H, CH2-O), 6.86 (m, 8 H, C6H4 from <strong>[14174-09-5]dibenzo-24-crown-8</strong>), 7.25 (m, 1H, p-ArH), 7.40 (t, 2H, m-ArH), 8.08 (d, 2H, o-ArH) ppm. 13C NMR (75 MHz, CDCl3, 25 C): delta 68.7, 69.7, 70.4 (C-O), 114.1, 121.8, 148.6 (C6H4 from <strong>[14174-09-5]dibenzo-24-crown-8</strong>), 124.1 (o-C), 127.3 (p-C), 128.5 (m-C) ppm. FAB+ m/z (%): 581 [Cs(<strong>[14174-09-5]dibenzo-24-crown-8</strong>)+] (1 0 0), 758 [M+] (11). Anal. Calcd for C31H37CsN4O8S (758.62): C, 49.07; H, 4.88. Found: C, 48.6; H, 5.07.
Reference： [1]Inorganica Chimica Acta,2018,vol. 475,p. 83 - 89
  • 88
  • [ 14174-09-5 ]
  • [ 1196083-55-2 ]
  • C22H30N4O3*F6P(1-)*H(1+) [ No CAS ]
  • C63H76N8O6S2*2F6P(1-)*2C24H32O8*2H(1+) [ No CAS ]
Reference： [1]Organic Letters,2018,vol. 20,p. 5626 - 5630

Tags: 14174-09-5 synthesis path| 14174-09-5 SDS| 14174-09-5 COA| 14174-09-5 purity| 14174-09-5 application| 14174-09-5 NMR| 14174-09-5 COA| 14174-09-5 structure

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