213:
428:
337:
24:
350:
262:
120:
380:
and other analogs by both having a chiral axis and being a scaffold for certain chemical reactions. NOBIN is an excellent catalyst for the
227:
357:
191:
391:
Though rotation around the bond joining the rings is limited by the hydrogen atoms, enantiomerically pure NOBIN may
151:
485:
236:
InChI=1S/C20H15NO/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,22H,21H2
157:
480:
415:
385:
373:
246:
InChI=1/C20H15NO/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12,22H,21H2
36:
208:
62:
475:
411:
140:
285:
91:
79:
72:
403:
406:. The oxidative source is metal ions in solution such as Fe or a Cu amine complex. Once
212:
381:
328:
469:
179:
392:
418:, in which the basic group of NOBIN is used to form a diastereomeric salt of one
427:
419:
399:
313:
131:
407:
166:
372:(2-amino-2'-hydroxy-1,1'-binaphthyl) is an organic molecule used for
327:
Except where otherwise noted, data are given for materials in their
426:
377:
119:
109:
23:
196:
384:
producing reliable products, good yields, and excellent
345:
422:. The other enantiomer however will stay in solution.
458:
Ding, Li; Ten years of research on NOBIN chemistry:
398:NOBIN is prepared by oxidative cross coupling of
178:
90:
78:
71:
8:
270:OC1=C(C2=C(C=CC=C3)C3=CC=C2N)C4=CC=CC=C4C=C1
211:
139:
15:
267:
232:
207:
156:
239:Key: HIXQCPGXQVQHJP-UHFFFAOYSA-N
7:
414:. One method for this is the use of
249:Key: HIXQCPGXQVQHJP-UHFFFAOYAR
169:
451:Kocovsky, Smrcina, Lorenc, Hanus;
410:NOBIN is produced, it needs to be
50:2-Amino-2'-hydroxy-1,1'-binaphthyl
14:
335:
303:
297:
22:
431:The two enantiomers of NOBIN, (
331:(at 25 °C , 100 kPa).
306:
291:
1:
502:
460:Current Organic Synthesis
325:
278:
258:
223:
55:
47:
35:
30:
21:
435:)-(-)-NOBIN (left) and (
440:
376:. NOBIN is related to
430:
416:camphorsulfonic acid
386:diastereoselectivity
374:asymmetric catalysis
37:Preferred IUPAC name
439:)-(+)-NOBIN (right)
321: g·mol
18:
441:
358:Infobox references
16:
462:;(2005);2;499-545
366:Chemical compound
364:
363:
192:CompTox Dashboard
121:Interactive image
493:
348:
342:
339:
338:
320:
308:
305:
299:
293:
286:Chemical formula
216:
215:
200:
198:
182:
171:
160:
143:
123:
94:
82:
75:
26:
19:
501:
500:
496:
495:
494:
492:
491:
490:
466:
465:
448:
404:2-naphthylamine
367:
360:
355:
354:
353: ?)
344:
340:
336:
332:
318:
302:
296:
288:
274:
271:
266:
265:
254:
251:
250:
247:
241:
240:
237:
231:
230:
219:
201:
194:
185:
172:
146:
126:
113:
102:
65:
51:
43:
42:
12:
11:
5:
499:
497:
489:
488:
486:Naphthylamines
483:
478:
468:
467:
464:
463:
456:
447:
444:
443:
442:
395:upon heating.
382:aldol reaction
365:
362:
361:
356:
334:
333:
329:standard state
326:
323:
322:
316:
310:
309:
300:
294:
289:
284:
281:
280:
276:
275:
273:
272:
269:
261:
260:
259:
256:
255:
253:
252:
248:
245:
244:
242:
238:
235:
234:
226:
225:
224:
221:
220:
218:
217:
209:DTXSID30929912
204:
202:
190:
187:
186:
184:
183:
175:
173:
165:
162:
161:
154:
148:
147:
145:
144:
136:
134:
128:
127:
125:
124:
116:
114:
107:
104:
103:
101:
100:
88:
76:
68:
66:
61:
58:
57:
53:
52:
49:
45:
44:
40:
39:
33:
32:
28:
27:
13:
10:
9:
6:
4:
3:
2:
498:
487:
484:
482:
479:
477:
474:
473:
471:
461:
457:
454:
450:
449:
445:
438:
434:
429:
425:
424:
423:
421:
417:
413:
409:
405:
401:
396:
394:
389:
387:
383:
379:
375:
371:
359:
352:
347:
330:
324:
317:
315:
312:
311:
290:
287:
283:
282:
277:
268:
264:
257:
243:
233:
229:
222:
214:
210:
206:
205:
203:
193:
189:
188:
181:
177:
176:
174:
168:
164:
163:
159:
155:
153:
150:
149:
142:
138:
137:
135:
133:
130:
129:
122:
118:
117:
115:
111:
106:
105:
98:
93:
89:
86:
81:
77:
74:
70:
69:
67:
64:
60:
59:
54:
46:
41:2′-Amino-2-ol
38:
34:
29:
25:
20:
459:
452:
436:
432:
397:
390:
369:
368:
96:
84:
56:Identifiers
48:Other names
481:2-Naphthols
455:;(1991) 231
279:Properties
92:137848-29-4
80:137848-28-3
73:134532-03-9
470:Categories
446:References
420:enantiomer
400:2-naphthol
314:Molar mass
132:ChemSpider
108:3D model (
63:CAS Number
476:Catalysts
412:resolved
393:racemize
453:Synlett
408:racemic
351:what is
349: (
319:285.346
180:3617797
167:PubChem
158:C493913
141:2852904
95: (
83: (
346:verify
343:
263:SMILES
31:Names
17:NOBIN
378:BINOL
370:NOBIN
228:InChI
110:JSmol
402:and
152:MeSH
197:EPA
170:CID
472::
388:.
301:15
295:20
437:R
433:S
341:N
307:O
304:N
298:H
292:C
199:)
195:(
112:)
99:)
97:S
87:)
85:R
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
