667:
31:
637:
207:
173:
652:
188:
143:
128:
588:
158:
222:
507:
622:
607:
679:
785:
254:
236:
724:. Owing to their extended conjugation, α,β-unsaturated carbonyls are prone to polymerization. In terms of industrial scale, polymerization dominates the use of α,β-unsaturated carbonyls. Again because of their electrophilic character, the alkene portion of α,β-unsaturated carbonyls is good dienophiles in
79:). Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called
728:. They can be further activated by Lewis acids, which bind to the carbonyl oxygen. α,β-Unsaturated carbonyls are good ligands for low-valent metal complexes, examples being
979:
944:
942:
Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut (2003). "Acrylic Acid and
Derivatives".
1045:
Ito, Y.; Fujii, S.; Nakatuska, M.; Kawamoto, F.; Saegusa, T. (1979). "One-Carbon Ring
Expansion of Cycloalkanones to Conjugated Cycloalkenones: 2-Cyclohepten-1-One".
666:
796:
Since α,β-unsaturated compounds are electrophiles and alkylating agents, many α,β-unsaturated carbonyl compounds are toxic. The endogenous scavenger compound
370:
and α,β-unsaturated esters, respectively. They also polymerize readily. Acrylic acid, its esters, and its amide derivatives feature the acryloyl group.
651:
736:
127:
927:
729:
636:
206:
142:
76:
587:
172:
996:
891:
858:
485:
187:
961:
157:
750:
754:
1147:
1142:
778:
606:
1137:
621:
118:α,β-Unsaturated carbonyl compounds can be subclassified according to the nature of the carbonyl and alkene groups.
500:
725:
457:
398:
221:
774:
496:
346:
are derived from but do not contain the acrylate group. The carboxyl group of acrylic acid can react with
917:
742:α,β-Unsaturated carbonyls are readily hydrogenated. Hydrogenation can target the carbonyl or the alkene (
765:α,β-Unsaturated thioesters are intermediates in several enzymatic processes. Two prominent examples are
30:
766:
292:
261:α,β-Unsaturated carbonyl compounds featuring a carbonyl conjugated to an alkene that is terminal, or
816:
770:
743:
492:
441:
355:
133:
1113:
709:
481:
453:
678:
1105:
1097:
1078:
992:
957:
923:
887:
854:
556:
469:
437:
323:
227:
68:
63:, but also carboxylic acids and the corresponding esters and amides. In these compounds, the
1087:
1054:
1025:
984:
949:
879:
846:
801:
713:
394:
343:
52:
1152:
386:
363:
327:
163:
104:
642:
597:
575:
524:
520:
100:
64:
506:
1131:
717:
697:
612:
568:
528:
465:
235:
88:
1117:
704:
carbon as well as the β-carbon. Depending on conditions, either site is attacked by
307:. Compounds containing an acryloyl group can be referred to as "acrylic compounds".
684:
627:
382:
339:
288:
212:
92:
953:
338:
H). These compounds are prone to polymerization, giving rise to the large area of
800:
naturally protects from toxic electrophiles in the body. Some drugs (amifostine,
913:
797:
705:
657:
378:
193:
96:
1092:
1073:
784:
721:
477:
351:
178:
80:
1101:
1058:
1030:
1013:
988:
489:
390:
559:
to the carbonyl group of the aldehyde (formyl group). The simplest enal is
17:
1109:
883:
850:
701:
560:
552:
510:
General reaction for an aldol condensation between two carbonyl compounds
414:
270:
241:
148:
84:
253:
473:
461:
347:
262:
548:
433:
429:
410:
320:
280:
276:
72:
807:) containing thiol groups may protect from such harmful alkylation.
460:. Some commercially significant enones produced by condensations of
319:
is a type of α,β-unsaturated carbonyl compound that consists of an
1074:"Structure and mechanism of action of the Acyl-CoA dehydrogenases"
505:
409:"Enone" redirects here. For the character in Greek mythology, see
367:
359:
252:
56:
919:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
821:
284:
99:. Unsaturated carbonyls can be prepared in the laboratory in an
60:
55:
with the general structure (O=CR)−C=C-R. Such compounds include
436:
functional groups. In an α,β-unsaturated enone, the alkene is
555:
functional groups. In an α,β-unsaturated enal, the alkene is
385:. Maleic acid forms esters, an imide, and an anhydride, i.e.
783:
495:. Another method to access α,β-unsaturated carbonyls is via
440:
to the carbonyl group of the ketone. The simplest enone is
977:
Siegel, Hardo; Eggersdorfer, Manfred (2000). "Ketones".
397:. Fumaric acid, as fumarate, is an intermediate in the
34:
General structure of α,β-unsaturated carbonyl compounds.
660:, a particularly electrophilic α,β-unsaturated carbonyl
413:. For enone biomolecules used in paleothermometry, see
366:
are commercially important examples of α,β-unsaturated
377:
carbonyls are also common. The parent compounds are
716:, which is used commercially in the conversion of
1012:Ross, A. G.; Li, X.; Danishefsky, S. J. (2012).
1072:Thorpe, Colin; Kim, Jujng-Ja P. (1 June 1995).
980:Ullmann's Encyclopedia of Industrial Chemistry
945:Ullmann's Encyclopedia of Industrial Chemistry
922:(6th ed.), New York: Wiley-Interscience,
401:, which is of great importance in bioenergy.
8:
878:. Patai's Chemistry of Functional Groups.
874:Patai, Saul; Rappoport, Zvi, eds. (1989).
845:. Patai's Chemistry of Functional Groups.
841:Patai, Saul; Rappoport, Zvi, eds. (1989).
746:) selectively, or both functional groups.
452:). Enones are typically produced using an
330:. The simplest example is acrylic acid (CH
1091:
1029:
547:) is an organic compound containing both
428:) is an organic compound containing both
311:α,β-Unsaturated acids, esters, and amides
737:tris(dibenzylideneacetone)dipalladium(0)
712:. One type of conjugate addition is the
499:. Cyclic enones can be prepared via the
83:. Examples of unsaturated carbonyls are
29:
907:
905:
903:
833:
580:
151:, the simplest α,β-unsaturated aldehyde
120:
692:Reactions of α,β-unsaturated carbonyls
708:. Additions to the alkene are called
136:, the simplest α,β-unsaturated ketone
27:Functional group of organic compounds
7:
600:, an enal that exists as an isomer
49:α,β-Unsaturated carbonyl compounds
25:
672:Enone complex of iron tricarbonyl
677:
665:
650:
635:
620:
605:
586:
567:=CHCHO). Other examples include
234:
220:
205:
186:
171:
156:
141:
126:
122:Parent α,β-Unsaturated Carbonyls
781:(FAD) is a required co-factor.
582:Other α,β-Unsaturated Carbonyls
303:or simply (and incorrectly) as
257:Structure of the acryloyl group
1014:"Preparation of Cyclobutenone"
773:. They arise by the action of
696:α,β-Unsaturated carbonyls are
1:
954:10.1002/14356007.a01_161.pub2
574:(essence of mowed lawns) and
488:, the starting compound is a
181:, precursor to polyacrylamide
44:can also be single hydrogens.
751:Nazarov cyclization reaction
486:Meyer–Schuster rearrangement
779:Flavin adenine dinucleotide
215:, isomeric with maleic acid
1169:
1093:10.1096/fasebj.9.9.7601336
761:α,β-Unsaturated thioesters
519:The cyclic enones include
408:
299:, and it is also known as
166:, an α,β-unsaturated ester
1059:10.15227/orgsyn.059.0113
1031:10.15227/orgsyn.089.0491
989:10.1002/14356007.a15_077
458:Knoevenagel condensation
983:. Weinheim: Wiley-VCH.
948:. Weinheim: Wiley-VCH.
775:acyl-CoA dehydrogenases
755:Rauhut–Currier reaction
578:(essence of cinnamon).
399:Krebs citric acid cycle
788:
630:, the male sex hormone
531:, and cycloheptenone.
511:
497:selenoxide elimination
258:
45:
884:10.1002/9780470772225
876:Enones: Vol. 2 (1989)
851:10.1002/9780470772218
843:Enones: Vol. 1 (1989)
787:
726:Diels–Alder reactions
645:, essence of cinnamon
615:, common cyclic enone
509:
501:Pauson–Khand reaction
256:
196:, an α,β-unsaturated
75:(hence the adjective
33:
767:coumaroyl-coenzyme A
358:to form an acrylate
317:α,β-unsaturated acid
293:preferred IUPAC name
912:Smith, Michael B.;
817:2-alkenal reductase
771:crotonyl-coenzyme A
749:Enones undergo the
744:conjugate reduction
710:conjugate additions
442:methyl vinyl ketone
287:group derived from
134:Methyl vinyl ketone
1148:Alkene derivatives
1143:Conjugated ketones
789:
512:
454:aldol condensation
259:
46:
1138:Functional groups
1079:The FASEB Journal
1047:Organic Syntheses
1018:Organic Syntheses
929:978-0-471-72091-1
523:, cyclobutenone,
381:and the isomeric
362:. Acrylamide and
344:Acrylate polymers
295:for the group is
228:Acryloyl chloride
53:organic compounds
16:(Redirected from
1160:
1122:
1121:
1095:
1069:
1063:
1062:
1042:
1036:
1035:
1033:
1009:
1003:
1002:
974:
968:
967:
939:
933:
932:
909:
898:
897:
871:
865:
864:
838:
757:(dimerization).
714:Michael addition
681:
669:
654:
639:
624:
609:
590:
472:of acetone) and
395:maleic anhydride
373:α,β-Unsaturated
238:
224:
209:
190:
175:
160:
145:
130:
21:
1168:
1167:
1163:
1162:
1161:
1159:
1158:
1157:
1128:
1127:
1126:
1125:
1071:
1070:
1066:
1044:
1043:
1039:
1011:
1010:
1006:
999:
976:
975:
971:
964:
941:
940:
936:
930:
911:
910:
901:
894:
873:
872:
868:
861:
840:
839:
835:
830:
813:
805:-acetylcysteine
794:
763:
733:
694:
687:
682:
673:
670:
661:
655:
646:
640:
631:
625:
616:
610:
601:
591:
566:
537:
517:
451:
447:
418:
407:
387:diethyl maleate
364:methyl acrylate
337:
333:
328:carboxylic acid
313:
283:)−); it is the
275:
251:
244:
239:
230:
225:
216:
210:
201:
191:
182:
176:
167:
164:Methyl acrylate
161:
152:
146:
137:
131:
116:
114:Classifications
110:
105:Perkin reaction
43:
39:
35:
28:
23:
22:
15:
12:
11:
5:
1166:
1164:
1156:
1155:
1150:
1145:
1140:
1130:
1129:
1124:
1123:
1086:(9): 718–725.
1064:
1037:
1004:
997:
969:
962:
934:
928:
899:
892:
866:
859:
832:
831:
829:
826:
825:
824:
819:
812:
809:
793:
790:
762:
759:
731:
693:
690:
689:
688:
683:
676:
674:
671:
664:
662:
656:
649:
647:
643:Cinnamaldehyde
641:
634:
632:
626:
619:
617:
611:
604:
602:
598:Crotonaldehyde
592:
585:
583:
576:cinnamaldehyde
564:
536:
533:
525:cyclopentenone
521:cyclopropenone
516:
513:
449:
445:
406:
403:
335:
331:
312:
309:
273:
267:acryloyl group
265:, contain the
250:
249:Acryloyl group
247:
246:
245:
240:
233:
231:
226:
219:
217:
211:
204:
202:
192:
185:
183:
177:
170:
168:
162:
155:
153:
147:
140:
138:
132:
125:
123:
115:
112:
101:aldol reaction
65:carbonyl group
41:
37:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1165:
1154:
1151:
1149:
1146:
1144:
1141:
1139:
1136:
1135:
1133:
1119:
1115:
1111:
1107:
1103:
1099:
1094:
1089:
1085:
1081:
1080:
1075:
1068:
1065:
1060:
1056:
1052:
1048:
1041:
1038:
1032:
1027:
1023:
1019:
1015:
1008:
1005:
1000:
998:9783527306732
994:
990:
986:
982:
981:
973:
970:
965:
959:
955:
951:
947:
946:
938:
935:
931:
925:
921:
920:
915:
908:
906:
904:
900:
895:
893:9780470772225
889:
885:
881:
877:
870:
867:
862:
860:9780470772218
856:
852:
848:
844:
837:
834:
827:
823:
820:
818:
815:
814:
810:
808:
806:
804:
799:
791:
786:
782:
780:
776:
772:
768:
760:
758:
756:
752:
747:
745:
740:
738:
734:
727:
723:
719:
718:mesityl oxide
715:
711:
707:
703:
699:
698:electrophilic
691:
686:
680:
675:
668:
663:
659:
653:
648:
644:
638:
633:
629:
623:
618:
614:
613:Cyclohexenone
608:
603:
599:
595:
589:
584:
581:
579:
577:
573:
571:
562:
558:
554:
550:
546:
542:
534:
532:
530:
529:cyclohexenone
526:
522:
515:Cyclic enones
514:
508:
504:
502:
498:
494:
491:
487:
483:
479:
475:
471:
467:
466:mesityl oxide
463:
459:
455:
444:(butenone, CH
443:
439:
435:
431:
427:
423:
416:
412:
404:
402:
400:
396:
392:
388:
384:
380:
376:
371:
369:
365:
361:
357:
354:, or with an
353:
349:
345:
341:
329:
325:
322:
318:
310:
308:
306:
302:
298:
294:
290:
286:
282:
278:
272:
268:
264:
255:
248:
243:
237:
232:
229:
223:
218:
214:
208:
203:
199:
195:
189:
184:
180:
174:
169:
165:
159:
154:
150:
144:
139:
135:
129:
124:
121:
119:
113:
111:
108:
106:
102:
98:
94:
90:
89:mesityl oxide
86:
82:
78:
74:
70:
66:
62:
58:
54:
50:
32:
19:
1083:
1077:
1067:
1050:
1046:
1040:
1021:
1017:
1007:
978:
972:
943:
937:
918:
914:March, Jerry
875:
869:
842:
836:
802:
795:
764:
748:
741:
706:nucleophiles
700:at both the
695:
685:Squaric acid
628:testosterone
593:
569:
544:
540:
538:
518:
425:
421:
419:
383:fumaric acid
374:
372:
340:polyacrylate
316:
314:
304:
300:
297:prop-2-enoyl
296:
289:acrylic acid
266:
260:
213:Fumaric acid
197:
117:
109:
93:acrylic acid
87:(propenal),
48:
47:
798:glutathione
753:and in the
730:Fe(bda)(CO)
658:Paraquinone
484:). In the
379:maleic acid
194:Maleic acid
103:and in the
97:maleic acid
77:unsaturated
18:Acryl group
1132:Categories
963:3527306730
828:References
722:isophorone
572:-3-hexenal
557:conjugated
478:isophorone
438:conjugated
352:acrylamide
342:plastics.
324:conjugated
179:Acrylamide
81:vinylogous
69:conjugated
1102:0892-6638
490:propargyl
391:maleimide
1118:42549744
916:(2007),
811:See also
702:carbonyl
561:acrolein
553:aldehyde
426:alkenone
415:Alkenone
350:to form
242:Chalcone
200:carbonyl
149:Acrolein
85:acrolein
71:with an
1110:7601336
1053:: 113.
1024:: 491.
545:alkenal
493:alcohol
482:trimers
474:phorone
462:acetone
448:=CHCOCH
356:alcohol
348:ammonia
301:acrylyl
279:=CH−C(=
263:vinylic
40:& R
1153:Enones
1116:
1108:
1100:
995:
960:
926:
890:
857:
792:Safety
549:alkene
434:ketone
430:alkene
411:Oenone
405:Enones
393:, and
368:amides
321:alkene
291:. The
95:, and
73:alkene
57:enones
1114:S2CID
720:into
535:Enals
470:dimer
422:enone
360:ester
334:=CHCO
326:to a
305:acryl
61:enals
1106:PMID
1098:ISSN
993:ISBN
958:ISBN
924:ISBN
888:ISBN
855:ISBN
822:Enol
769:and
735:and
551:and
543:(or
541:enal
476:and
464:are
432:and
424:(or
285:acyl
59:and
51:are
1088:doi
1055:doi
1026:doi
985:doi
950:doi
880:doi
847:doi
570:cis
563:(CH
539:An
456:or
420:An
315:An
67:is
1134::
1112:.
1104:.
1096:.
1082:.
1076:.
1051:59
1049:.
1022:89
1020:.
1016:.
991:.
956:.
902:^
886:.
853:.
777:.
739:.
527:,
503:.
389:,
375:di
198:di
107:.
91:,
1120:.
1090::
1084:9
1061:.
1057::
1034:.
1028::
1001:.
987::
966:.
952::
896:.
882::
863:.
849::
803:N
732:3
596:-
594:E
565:2
480:(
468:(
450:3
446:2
417:.
336:2
332:2
281:O
277:C
274:2
271:H
269:(
42:4
38:2
36:R
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
