HRID4466

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

结构：COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.O.O.O.O.O

HCID11979419

未命名化合物

PRODUCTS

生成物

HCID996

Phenol

C6H6O

HCID11979419

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Cu+2]

催化剂HCID18616

Nitric acid, copper(2+) salt (2:1)

CuN2O6

溶剂HCID176

Acetic Acid

C2H4O2

2 次

PROCEDURE

实验过程

In 3 ml of acetic acid, 100 mg of TPC-A was dissolved and a solution of copper nitrate (40 mg) in 3 ml of acetic acid was added under stirring. When the color change of the reaction solution from blue to green took place under the continuation of stirring, water was added to cease the reaction and the product was extracted with ethyl acetate. After washing the extract with saturated sodium chloride solution and drying the extract over anhydrous magnesium sulfate, the extract was subjected to distillation to remove solvent, in vacuo and the product was recrystallized from methanol to obtain nitro compound of TPC-A at α-position of phenol thereof (108 mg) as yellow needle crystal having m.p. of 244°-250° C. (decomp) and [α]D22 of -232° (CHCl3).

WORKUP

后处理

stirringof stirring
customthe reaction
extractionthe product was extracted with ethyl acetate
washAfter washing the
extractionextract with saturated sodium chloride solution
customdrying the
extractionextract over anhydrous magnesium sulfate
distillationthe extract was subjected to distillation
customto remove solvent
customin vacuo and the product was recrystallized from methanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a80267a6bf2b4049a16df416b032a024
来源数据集: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04725578
来源说明: uspto-grants-1988_02

反应 SMILES

[CH3:1][C@@H:2]1[NH:37][C:35](=[O:36])[C@@H:34]2[N:38]([CH3:41])[C:39](=[O:40])[C@@H:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[C:31]([CH2:33]2)[CH:30]=[CH:29][C:28]=4[OH:42])=[CH:22][CH:21]=3)[N:17]([CH3:43])[C:15](=[O:16])[C@@H:14]([CH3:44])[NH:13][C:11](=[O:12])[C@H:10]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=2)[N:9]([CH3:54])[C:7](=[O:8])[C@H:6]([CH3:55])[NH:5][C:3]1=[O:4].[CH3:56][C@@H:57]1[NH:92][C:90](=[O:91])[C@@H:89]2[N:93]([CH3:96])[C:94](=[O:95])[C@@H:73]([CH2:74][C:75]3[CH:80]=[CH:79][C:78]([O:81][C:82]4[CH:87]=[C:86]([CH2:88]2)[CH:85]=[CH:84][C:83]=4[OH:97])=[CH:77][CH:76]=3)[N:72]([CH3:98])[C:70](=[O:71])[C@@H:69]([CH3:99])[NH:68][C:66](=[O:67])[C@H:65]([CH2:100][C:101]2[CH:106]=[CH:105][C:104]([O:107][CH3:108])=[CH:103][CH:102]=2)[N:64]([CH3:109])[C:62](=[O:63])[C@H:61]([CH3:110])[NH:60][C:58]1=[O:59].[CH3:111][C@@H:112]1[NH:147][C:145](=[O:146])[C@@H:144]2[N:148]([CH3:151])[C:149](=[O:150])[C@@H:128]([CH2:129][C:130]3[CH:135]=[CH:134][C:133]([O:136][C:137]4[CH:142]=[C:141]([CH2:143]2)[CH:140]=[CH:139][C:138]=4[OH:152])=[CH:132][CH:131]=3)[N:127]([CH3:153])[C:125](=[O:126])[C@@H:124]([CH3:154])[NH:123][C:121](=[O:122])[C@H:120]([CH2:155][C:156]2[CH:161]=[CH:160][C:159]([O:162][CH3:163])=[CH:158][CH:157]=2)[N:119]([CH3:164])[C:117](=[O:118])[C@H:116]([CH3:165])[NH:115][C:113]1=[O:114].[CH3:166][C@@H:167]1[NH:202][C:200](=[O:201])[C@@H:199]2[N:203]([CH3:206])[C:204](=[O:205])[C@@H:183]([CH2:184][C:185]3[CH:190]=[CH:189][C:188]([O:191][C:192]4[CH:197]=[C:196]([CH2:198]2)[CH:195]=[CH:194][C:193]=4[OH:207])=[CH:187][CH:186]=3)[N:182]([CH3:208])[C:180](=[O:181])[C@@H:179]([CH3:209])[NH:178][C:176](=[O:177])[C@H:175]([CH2:210][C:211]2[CH:216]=[CH:215][C:214]([O:217][CH3:218])=[CH:213][CH:212]=2)[N:174]([CH3:219])[C:172](=[O:173])[C@H:171]([CH3:220])[NH:170][C:168]1=[O:169].[OH2:221].O.O.O.O.O>C(O)(=O)C.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O>[CH3:1][C@@H:2]1[NH:37][C:35](=[O:36])[C@@H:34]2[N:38]([CH3:41])[C:39](=[O:40])[C@@H:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[C:31]([CH2:33]2)[CH:30]=[CH:29][C:28]=4[OH:42])=[CH:22][CH:21]=3)[N:17]([CH3:43])[C:15](=[O:16])[C@@H:14]([CH3:44])[NH:13][C:11](=[O:12])[C@H:10]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=2)[N:9]([CH3:54])[C:7](=[O:8])[C@H:6]([CH3:55])[NH:5][C:3]1=[O:4].[CH3:56][C@@H:57]1[NH:92][C:90](=[O:91])[C@@H:89]2[N:93]([CH3:96])[C:94](=[O:95])[C@@H:73]([CH2:74][C:75]3[CH:80]=[CH:79][C:78]([O:81][C:82]4[CH:87]=[C:86]([CH2:88]2)[CH:85]=[CH:84][C:83]=4[OH:97])=[CH:77][CH:76]=3)[N:72]([CH3:98])[C:70](=[O:71])[C@@H:69]([CH3:99])[NH:68][C:66](=[O:67])[C@H:65]([CH2:100][C:101]2[CH:106]=[CH:105][C:104]([O:107][CH3:108])=[CH:103][CH:102]=2)[N:64]([CH3:109])[C:62](=[O:63])[C@H:61]([CH3:110])[NH:60][C:58]1=[O:59].[CH3:111][C@@H:112]1[NH:147][C:145](=[O:146])[C@@H:144]2[N:148]([CH3:151])[C:149](=[O:150])[C@@H:128]([CH2:129][C:130]3[CH:135]=[CH:134][C:133]([O:136][C:137]4[CH:142]=[C:141]([CH2:143]2)[CH:140]=[CH:139][C:138]=4[OH:152])=[CH:132][CH:131]=3)[N:127]([CH3:153])[C:125](=[O:126])[C@@H:124]([CH3:154])[NH:123][C:121](=[O:122])[C@H:120]([CH2:155][C:156]2[CH:161]=[CH:160][C:159]([O:162][CH3:163])=[CH:158][CH:157]=2)[N:119]([CH3:164])[C:117](=[O:118])[C@H:116]([CH3:165])[NH:115][C:113]1=[O:114].[CH3:166][C@@H:167]1[NH:202][C:200](=[O:201])[C@@H:199]2[N:203]([CH3:206])[C:204](=[O:205])[C@@H:183]([CH2:184][C:185]3[CH:190]=[CH:189][C:188]([O:191][C:192]4[CH:197]=[C:196]([CH2:198]2)[CH:195]=[CH:194][C:193]=4[OH:207])=[CH:187][CH:186]=3)[N:182]([CH3:208])[C:180](=[O:181])[C@@H:179]([CH3:209])[NH:178][C:176](=[O:177])[C@H:175]([CH2:210][C:211]2[CH:216]=[CH:215][C:214]([O:217][CH3:218])=[CH:213][CH:212]=2)[N:174]([CH3:219])[C:172](=[O:173])[C@H:171]([CH3:220])[NH:170][C:168]1=[O:169].[OH2:221].[OH2:4].[OH2:4].[OH2:4].[OH2:4].[C:23]1([OH:26])[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1