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Aza-crown ether

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Morooka, M.; Ohba, S.; Toriumi, K. (1992). "Electron-density distribution in crystals of 1,4,7,10,13,16-hexaazacyclooctadecanecobalt(III) trichloride, meso-[Co(hexaen)]Cl3 at 106 K".
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Bencini, Andrea; Bianchi, Antonio; Garcia-España, Enrique; Micheloni, Mauro; Ramirez, José Antonio (1999). "Proton coordination by polyamine compounds in aqueous solution".
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Gokel, G. W.; Barbour, L. J.; Ferdani, R.; Hu, J. (2002). "Lariat Ether Receptor Systems Show Experimental Evidence for Alkali Metal Cation Interactions".
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Reichenbach-Klinke, Roland; König, Burkhard (2002). "Metal complexes of azacrown ethers in molecular recognition and catalysis".
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Krakowiak, Krzysztof E.; Bradshaw, Jerald S.; Zamecka-Krakowiak, Daria J. (1989). "Synthesis of aza-crown ethers".
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Frensdorff, Hans K. (1971). "Stability constants of cyclic polyether complexes with univalent cations".
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The synthesis of aza crown ethers are subject to the challenges associated with the preparation of
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Atkins, T. J.; Richman, J. E.; Oettle, W. F. (1978). "1,4,7,10,13,16-Hexaazacyclooctadecane".
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Gatto, Vincent J.; Miller, Steven R.; Gokel, George W. (1990). "4,13-Diaza-18-Crown-6".
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In many aza-crown ethers some or all of the amines are tertiary. One example is the tri(
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Reed, David P.; Weisman, Gary R. (2002). "1,4,7,10-Tetraazacyclododecane".
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can be synthesized by combining two triamine components. By reaction with
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crown ethers, which feature sidearms that augment complexation of cation.
353: 220: 60: 609: 582: 663: 463: 381: 317: 179: 138: 76: 80: 64: 18: 356:, three-dimensional aza crowns, feature tertiary amines. 133:, where n = 3, 4, 5, 6. Well-studied aza crowns include 368:
ether and amines.. One example is the diaza-18-crown-6,
39:. Color code: blue = N, gray = C, black = C, white = H. 16:
Ring molecule with several amine (–N– or >N–) groups
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Journal of the Chemical Society, Dalton Transactions
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Acta Crystallographica Section B: Structural Science
364:Another large class of macrocyclic ligands feature 380:The presence of the amine allows the formation of 242:is an aza-crown of the mixed ether-amine variety. 280:. This compound serves as a building block for 276:is converted to a derivative with two secondary 8: 219:, a derivative of cyclam, is used to treat 182:is a tetraaza crown ether with alternating 300:Aza crowns often feature trimethylene ((CH 598:Journal of the American Chemical Society 502: 500: 292:Many kinds of aza crown ethers exist. 200: 196: 189: 185: 127: 123: 119: 106: 102: 98: 34: 30: 26: 392: 161:1,4,7-Trimethyl-1,4,7-triazacyclononane 149:Selected aza-crowns and their complexes 147: 59:(cyclic polyether). That is, it has a 320:(1,4,8,11-tetraazacyclotetradecane). 7: 14: 548:10.2165/00126839-200708020-00006 232: 209: 172: 153: 116:-crown ethers have the formulae 95:crown ethers have the formulae 429:Coordination Chemistry Reviews 204:linkers between amine centers. 163:, a tridentate ligand used in 1: 441:10.1016/S0010-8545(98)00243-4 256:. The 18-membered ring in (CH 316:) linkages. One example is 732: 350:trimethyltriazacyclononane 308:) as well as ethylene ((CH 414:10.1107/S0108768192002714 360:Mixed ether-amine ligands 637:10.15227/orgsyn.068.0227 521:10.15227/orgsyn.058.0086 491:10.15227/orgsyn.078.0073 296:Variable length linkers 165:coordination chemistry 40: 22: 542:(2): 113–119. 2007. 610:10.1021/ja00732a007 583:10.1021/cr00094a008 274:diethylene triamine 75:) in place of each 143:hexaaza-18-crown-6 41: 664:10.1021/ar000093p 625:Organic Syntheses 282:macrocyclizations 135:triazacyclononane 45:organic chemistry 23:The structure of 723: 711:Chelating agents 696:Secondary amines 676: 675: 647: 641: 640: 620: 614: 613: 593: 587: 586: 571:Chemical Reviews 566: 560: 559: 536:Drugs in R&D 531: 525: 524: 504: 495: 494: 474: 468: 467: 464:10.1039/b106367g 451: 445: 444: 424: 418: 417: 397: 236: 225:multiple myeloma 213: 203: 192: 176: 157: 132: 111: 86: 74: 70: 38: 731: 730: 726: 725: 724: 722: 721: 720: 701:Tertiary amines 681: 680: 679: 658:(10): 878–886. 649: 648: 644: 622: 621: 617: 595: 594: 590: 568: 567: 563: 533: 532: 528: 506: 505: 498: 476: 475: 471: 453: 452: 448: 426: 425: 421: 399: 398: 394: 390: 371: 347: 343: 339: 335: 324:Tertiary amines 315: 311: 307: 303: 290: 267: 263: 259: 250: 243: 237: 228: 214: 205: 202: 198: 194: 191: 187: 183: 177: 168: 158: 131: 125: 121: 117: 110: 104: 100: 96: 84: 72: 68: 49:aza-crown ether 36: 32: 28: 25:[Co(III)(CH 24: 17: 12: 11: 5: 729: 727: 719: 718: 713: 708: 706:Ethyleneamines 703: 698: 693: 683: 682: 678: 677: 652:Acc. Chem. Res 642: 615: 604:(3): 600–606. 588: 577:(4): 929–972. 561: 534:"Plerixafor". 526: 496: 469: 458:(2): 121–130. 446: 419: 408:(4): 459–463. 391: 389: 386: 378: 377: 376:Lariate crowns 369: 362: 361: 345: 341: 337: 333: 330:tertiary amine 326: 325: 313: 309: 305: 301: 298: 297: 289: 286: 270:tosyl chloride 265: 261: 257: 249: 246: 245: 244: 240:2.2.2-Cryptand 238: 231: 229: 215: 208: 206: 178: 171: 169: 159: 152: 150: 15: 13: 10: 9: 6: 4: 3: 2: 728: 717: 714: 712: 709: 707: 704: 702: 699: 697: 694: 692: 689: 688: 686: 673: 669: 665: 661: 657: 653: 646: 643: 638: 634: 630: 626: 619: 616: 611: 607: 603: 599: 592: 589: 584: 580: 576: 572: 565: 562: 557: 553: 549: 545: 541: 537: 530: 527: 522: 518: 514: 510: 503: 501: 497: 492: 488: 484: 480: 473: 470: 465: 461: 457: 450: 447: 442: 438: 434: 430: 423: 420: 415: 411: 407: 403: 396: 393: 387: 385: 383: 375: 374: 373: 367: 359: 358: 357: 355: 351: 331: 323: 322: 321: 319: 295: 294: 293: 287: 285: 283: 279: 275: 271: 255: 247: 241: 235: 230: 226: 222: 218: 212: 207: 181: 175: 170: 166: 162: 156: 151: 148: 146: 144: 141:(n = 4), and 140: 136: 130: 115: 112:, the parent 109: 94: 90: 87:) around the 82: 78: 66: 62: 58: 54: 50: 46: 21: 655: 651: 645: 628: 624: 618: 601: 597: 591: 574: 570: 564: 539: 535: 529: 512: 508: 482: 478: 472: 455: 449: 432: 428: 422: 405: 401: 395: 379: 365: 363: 327: 299: 291: 278:sulfonamides 251: 128: 113: 107: 91:. While the 48: 42: 716:Macrocycles 348:, known as 254:macrocycles 57:crown ether 691:Polyamines 685:Categories 509:Org. Synth 479:Org. Synth 435:: 97–156. 388:References 217:Plerixafor 51:is an aza 354:Cryptands 248:Synthesis 145:(n = 6). 137:(n = 3), 83:linkage, 67:linkage, 672:12379140 556:17324009 288:Variants 221:lymphoma 61:nitrogen 53:analogue 631:: 227. 670:  554:  515:: 86. 485:: 73. 382:Lariat 318:cyclam 180:Cyclam 139:cyclen 93:parent 79:atom ( 77:oxygen 73:>N− 63:atom ( 332:) (CH 81:ether 65:amine 55:of a 47:, an 668:PMID 552:PMID 366:both 223:and 193:and 89:ring 69:−NH− 660:doi 633:doi 606:doi 579:doi 544:doi 517:doi 487:doi 460:doi 437:doi 433:188 410:doi 340:NCH 264:NH) 195:(CH 184:(CH 126:NH) 118:(CH 114:aza 97:(CH 85:−O− 71:or 43:In 33:NH) 687:: 666:. 656:35 654:. 629:68 627:. 602:93 600:. 575:89 573:. 550:. 538:. 513:58 511:. 499:^ 483:78 481:. 431:. 406:48 404:. 372:. 352:. 336:CH 284:. 272:, 260:CH 122:CH 105:O) 101:CH 29:CH 674:. 662:: 639:. 635:: 612:. 608:: 585:. 581:: 558:. 546:: 540:8 523:. 519:: 493:. 489:: 466:. 462:: 443:. 439:: 416:. 412:: 370:2 346:3 344:) 342:3 338:2 334:2 314:2 312:) 310:2 306:3 304:) 302:2 266:6 262:2 258:2 227:. 201:3 199:) 197:2 190:2 188:) 186:2 167:. 129:n 124:2 120:2 108:n 103:2 99:2 37:] 35:6 31:2 27:2

Index


organic chemistry
analogue
crown ether
nitrogen
amine
oxygen
ether
ring
parent
triazacyclononane
cyclen
hexaaza-18-crown-6
1,4,7-Trimethyl-1,4,7-triazacyclononane, a tridentate ligand used in coordination chemistry.
1,4,7-Trimethyl-1,4,7-triazacyclononane
coordination chemistry
Cyclam is a tetraaza crown ether with alternating (CH2)2 and (CH2)3 linkers between amine centers.
Cyclam
Plerixafor, a derivative of cyclam, is used to treat lymphoma and multiple myeloma.
Plerixafor
lymphoma
multiple myeloma
2.2.2-Cryptand is an aza-crown of the mixed ether-amine variety.
2.2.2-Cryptand
macrocycles
tosyl chloride
diethylene triamine
sulfonamides
macrocyclizations
cyclam

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