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Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. DOI: PubMed ID:

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

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Product Details of [ 90-05-1 ]

CAS No. :90-05-1 MDL No. :MFCD00002185
Formula : C7H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LHGVFZTZFXWLCP-UHFFFAOYSA-N
M.W : 124.14 Pubchem ID :460
Synonyms :
2-Methoxyphenol;2-hydroxyanisole;O-methylcatechol;o-methoxyphenol
Chemical Name :2-Methoxyphenol

Calculated chemistry of [ 90-05-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.96
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 1.32
Log Po/w (WLOGP) : 1.4
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 1.4

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.87
Solubility : 1.68 mg/ml ; 0.0135 mol/l
Class : Very soluble
Log S (Ali) : -1.54
Solubility : 3.58 mg/ml ; 0.0289 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.91
Solubility : 1.54 mg/ml ; 0.0124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 90-05-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P261-P273-P270-P271-P264-P280-P302+P352-P312-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405 UN#:N/A
Hazard Statements:H302+H332-H313-H315-H319-H336-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 90-05-1 ]

* 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.

  • Upstream synthesis route of [ 90-05-1 ]
  • Downstream synthetic route of [ 90-05-1 ]

[ 90-05-1 ] Synthesis Path-Upstream   1~107

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YieldReaction ConditionsOperation in experiment
80% With sodium hydroxide In water Added 2.5 L of water to R.B Flask, 80 gms of NaOH was added and stirred to dissolve. Added 500 gms of Guaiacol, 1.12 Kg of Epichlorohydrine and stirred at 25-350C for 5-6 h. The organic layer was separated. To the Epichlorohydrine layer charged 160 gms NaOH dissolved in 2.5 L of water and stirred at 25-30°C for 3-4 h. The organic layer was separated and washed with 150 gms NaOH dissolved in 1.5 L of water. Excess Epichlorohydrine was recovered by distillation of the product layer at 90°C under vacuum (600-700 mmHg) to give 65 0-680 gms of oil. To the cmde oil was added 3.0 L of Isopropanol and cooled to 0°C and filtered the product to get 1-(2- Methoxy phenoxy)-2,3-epoxy propane (3).Yield: 80percent; purity >98percent.
72.2%
Stage #1: With tetrabutylammomium bromide; sodium hydroxide In water; N,N-dimethyl-formamide at 50℃; for 0.5 h; Inert atmosphere
Stage #2: for 1 h;
In a 100 mL three-neck flask, 2-methoxyphenol (1.24 g, 10 mmol) was added in succession.Sodium hydroxide (0.55 g, 13.7 mmol), tetrabutylammonium bromide (100 mg, 1 mmol),30mL DMF and 12mL water, nitrogen protection, stirring at 50 °C for 30min.Epichlorohydrin (2.76 g, 30 mmol) was added dropwise and the reaction was continued for 1 h.TLC showed that the reaction was almost complete and the reaction solution was concentrated.The pH was adjusted to 7 with acetic acid, and the mixture was extracted with ethyl acetate. The organic phase was dried, concentrated, and separated by column chromatography.Concentration under reduced pressure afforded 1.3 g of a colorless oily product in a yield of 72.2percent.
43% With sodium hydroxide In 1,4-dioxane; water for 3 h; Heating / reflux 2-(2-Methoxy-phenoxymethyl)-oxirane:
Epichlorohydrin (8.4 g, 91.3 mmol) was slowly added to a solution of 2-methoxyphenol (8 g, 64.4 mmol) dissolved in water (6 mL) and dioxane (20 mL) containing sodium hydroxide (2.9 g, 72.5 mmol).
The resulting mixture was heated at reflux for about 3 hours.
Following standard extractive workup with ether, the crude product was purified by flash column chromatography on silica gel (4*20 cm, petroleum ether/ethyl acetate=5/1 elution) to afford the title product (4.95 g, 43percent).
1H NMR (300 MHz, CDCl3) δ 6.99-6.89 (m, 4H), 4.24 (dd, 1H, J=8.4, 3.6 Hz), 4.05 (dd, 1H, J=9.6, 5.4 Hz), 3.88 (s, 3H), 3.43-3.38 (m, 1H), 2.90 (t, 1H, J=4.5 Hz), 2.76-2.74 (m, 1H); LC-MS: m/z=195 (MH)+.
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[2] Medicinal Chemistry Research, 2004, vol. 13, # 8-9, p. 631 - 642
[3] Synthetic Communications, 1994, vol. 24, # 6, p. 833 - 838
[4] Tetrahedron, 2006, vol. 62, # 47, p. 10968 - 10979
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 26, p. 6641 - 6644[6] Angew. Chem., 2014, p. 6759 - 6762,4
[7] RSC Advances, 2017, vol. 7, # 78, p. 49490 - 49497
[8] Patent: WO2016/142819, 2016, A2, . Location in patent: Page/Page column 17
[9] Polish Journal of Chemistry, 2009, vol. 83, # 4, p. 595 - 604
[10] Patent: CN107043361, 2017, A, . Location in patent: Sheet 0053; 0054; 0055; 0056
[11] Bioorganic and medicinal chemistry, 2003, vol. 11, # 16, p. 3513 - 3527
[12] Synthetic Communications, 2011, vol. 41, # 8, p. 1141 - 1145
[13] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 11, p. 1218 - 1222
[14] Journal of the Chemical Society, Chemical Communications, 1980, # 22, p. 1053 - 1054
[15] Patent: US2008/312247, 2008, A1, . Location in patent: Page/Page column 31
[16] Chem. Zentralbl., 1910, vol. 81, # I, p. 1134
[17] Journal of the Chemical Society, 1912, vol. 101, p. 309
[18] Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 586 - 593
[19] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 5, p. 738 - 747
[20] Tetrahedron Asymmetry, 2001, vol. 12, # 15, p. 2109 - 2119
[21] Patent: WO2010/23687, 2010, A2, . Location in patent: Page/Page column 14; 15
[22] Patent: WO2010/25370, 2010, A2, . Location in patent: Page/Page column 49
[23] Organic Process Research and Development, 2012, vol. 16, # 5, p. 748 - 754
[24] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5419 - 5423
[25] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5419 - 5423
[26] Green Chemistry, 2016, vol. 18, # 14, p. 4063 - 4072
[27] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 1173
  • 2
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  • [ 3132-64-7 ]
  • [ 2210-74-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3089 - 3104
[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 2, p. 345 - 351
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 20, p. 6108 - 6115
  • 3
  • [ 90-05-1 ]
  • [ 106-89-8 ]
  • [ 16929-60-5 ]
  • [ 2210-74-4 ]
Reference: [1] Patent: WO2008/47388, 2008, A2, . Location in patent: Page/Page column 12; 14
[2] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
  • 4
  • [ 90-05-1 ]
  • [ 106-89-8 ]
  • [ 25772-81-0 ]
  • [ 2210-74-4 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 47, p. 10968 - 10979
[2] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[3] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
  • 5
  • [ 90-05-1 ]
  • [ 106-89-8 ]
  • [ 25772-81-0 ]
  • [ 16929-60-5 ]
  • [ 93-14-1 ]
  • [ 2210-74-4 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
  • 6
  • [ 96-23-1 ]
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  • [ 2210-74-4 ]
Reference: [1] Chem. Zentralbl., 1910, vol. 81, # I, p. 1134
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 1173
  • 7
  • [ 90-05-1 ]
  • [ 7168-85-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 3029 - 3036
[2] Tetrahedron, 2015, vol. 71, # 29, p. 4835 - 4841
[3] Organic Letters, 2016, vol. 18, # 21, p. 5624 - 5627
[4] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2774 - 2779
  • 8
  • [ 90-05-1 ]
  • [ 20351-79-5 ]
Reference: [1] Chemische Berichte, 1925, vol. 58, p. 1955
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 4, p. 1022 - 1032
[3] ChemMedChem, 2012, vol. 7, # 3, p. 391 - 395
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YieldReaction ConditionsOperation in experiment
10 %Chromat. With sodium hydroxide In water at 20℃; for 24 h; Inert atmosphere To an aqueous solution of NaOH (20 wtpercent, 20 mL) wereadded guaiacol (5 mmol, 0.62 g) and zeolite (5 g) under N2atmosphere at room temperature. Then chloroform(20 mL) was dropped to the mixture. Dodecane (1 mmol,0.224 mL) was added as GC internal standard. The reactionmixture was stirred at room temperature for 24 h. Thereaction was quenched with 3 N aqueous HCl. The mixturewas extracted with ethyl acetate. The yield and selectivityof products was detected by GC.
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 1287
[2] Chemische Berichte, 1881, vol. 14, p. 2021
[3] Catalysis Letters, 2015, vol. 145, # 2, p. 712 - 714
[4] Catalysis Letters, 2015, vol. 145, # 2, p. 712 - 714
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YieldReaction ConditionsOperation in experiment
11.5%
Stage #1: With copper(I) oxide In trifluoroacetic acid for 5 h; Reflux
Stage #2: With hydrogenchloride In water at 20℃; for 1 h;
General procedure: To a solution of substrates (1a–1q, 0.15 mmol) in trifluoroacetic acid (5 ml), hexamethylenetetramine (0.3 mmol) and cuprous oxide (0.15 mmol) were added. The reaction mixture was refluxed for about 5 h, cooled to room temperature, followed by addition of hydrochloric acid (3 N, 5 ml). After stirring for another 1 h, the solution was concentrated under reduced pressure. The products were purified by silica gel column chromatography (200–300 mesh).
Reference: [1] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8147 - 8158
  • 11
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  • [ 148-53-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1939 - 1943
[2] Organic Letters, 2017, vol. 19, # 23, p. 6340 - 6343
[3] Organic Letters, 2018, vol. 20, # 10, p. 2880 - 2883
  • 12
  • [ 67-66-3 ]
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  • [ 148-53-8 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 2021
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 15, p. 1813 - 1819
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  • [ 76-03-9 ]
  • [ 148-53-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1927, vol. 46, p. 147
  • 14
  • [ 90-05-1 ]
  • [ 864131-95-3 ]
  • [ 148-53-8 ]
Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 2406
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  • [ 67-66-3 ]
  • [ 90-05-1 ]
  • [ 621-59-0 ]
  • [ 148-53-8 ]
  • [ 121-33-5 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 543 - 546
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 8, p. 543 - 546
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  • [ 148-53-8 ]
  • [ 121-33-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 764
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  • [ 32752-36-6 ]
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  • [ 148-53-8 ]
  • [ 121-33-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 764
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  • [ 91-78-1 ]
  • [ 148-53-8 ]
  • [ 121-33-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 764
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YieldReaction ConditionsOperation in experiment
62% With potassium carbonate; potassium iodide In acetone at 60℃; General procedure: A solution of 1,2-dibromoethane (0.02 mol) in 40 ml ofacetone was added dropwise into the mixture of respective phenol (0.08 mol) andK2CO3 (0.04 mol) in 30 ml of acetone. Subsequently, acatalytic amount of KI (0.3 mmol) was added and the resulting mixture wasstirred at 60°C for 24–72 hours. After the completion of the reaction theinorganic residues were filtrated off and organic mixture was concentrated undervacuum. The obtained crude product was purified on silica gel with AcOEt/hexaneas eluting system.
Reference: [1] Farmaco, Edizione Scientifica, 1986, vol. 41, # 10, p. 794 - 800
[2] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1997, p. 449 - 462
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 2, p. 809 - 817
[4] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 6, p. 527 - 531
[5] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 334 - 346
[6] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 9, p. 1241 - 1244
[7] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1897, vol. <5> 6 II, p. 33
[8] Chemische Berichte, 1910, vol. 43, p. 2179
[9] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1897, vol. <5> 6 II, p. 33
[10] Journal of Medicinal Chemistry, 1965, vol. 8, p. 356 - 367
[11] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 3, p. 719 - 730
[12] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 1900 - 1918
[13] Chinese Chemical Letters, 2010, vol. 21, # 3, p. 287 - 289
[14] Synthetic Communications, 2011, vol. 41, # 1, p. 85 - 93
[15] Chinese Journal of Chemistry, 2013, vol. 31, # 9, p. 1228 - 1233
[16] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5582 - 5591
[17] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 9, p. 931 - 935
  • 20
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  • [ 4463-59-6 ]
Reference: [1] Patent: US2003/212094, 2003, A1,
  • 21
  • [ 90-05-1 ]
  • [ 107-05-1 ]
  • [ 97-53-0 ]
  • [ 579-60-2 ]
Reference: [1] Patent: WO2015/15445, 2015, A2, . Location in patent: Paragraph 0119-0121
[2] Patent: CN105294409, 2016, A, . Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046
  • 22
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  • [ 107-05-1 ]
  • [ 97-53-0 ]
Reference: [1] Patent: US4048236, 1977, A,
  • 23
  • [ 90-05-1 ]
  • [ 97-53-0 ]
  • [ 579-60-2 ]
Reference: [1] Patent: US4048236, 1977, A,
[2] Patent: US4048236, 1977, A,
[3] Patent: US4048236, 1977, A,
[4] Patent: US4048236, 1977, A,
[5] Patent: US4048236, 1977, A,
[6] Patent: US4048236, 1977, A,
[7] Patent: US4048236, 1977, A,
  • 24
  • [ 4873-09-0 ]
  • [ 90-05-1 ]
  • [ 97-53-0 ]
Reference: [1] Synlett, 2003, # 10, p. 1431 - 1434
  • 25
  • [ 90-05-1 ]
  • [ 106-95-6 ]
  • [ 97-53-0 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 56, p. 7019 - 7021
  • 26
  • [ 90-05-1 ]
  • [ 97-53-0 ]
Reference: [1] Zhurnal Obshchei Khimii, 1941, vol. 11, p. 722,725[2] Chem.Abstr., 1942, p. 430
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YieldReaction ConditionsOperation in experiment
66% With potassium carbonate In acetonitrile £'rytftro-l-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-l,3-propanediol (2g): (0178) (0179) 2g (0180) Scheme 8. Synthesis of i?? i zro-l-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-l,3- propanediol (2g). This compound was prepared according to a literature procedure. (Buendia, J. ; (0181) Mottweiler, J.; Bolm, C. Chem. Eur. J. 2011, 17, 13877.) Spectral data were consistent with those reported in the literature. *H NMR (400 MHz, CDC13) δ 7.07 (ddd, J = 8.2 Hz, 7.2, 1.6, 1.6 Hz, 1H), 7.02-6.84 (M, 5H), 6.82 (D, J = 8.2 Hz, 1H), 4.98 (b t, J = 4.8 Hz, 1 H), 4.16 (ddd, J = 6.0, 4.8, 3.5 Hz, 1 H), 3.95-3.90 (m, 1H), 3.87 (s, 3H), 3.86 (s, 6H), 3.66 (ddd, J = 12.0, 7.2, 3.5 Hz, 1H), 2.87 ppm (b s, 1H). HRMS (EI) calculated for C18H2206Na [M + Na]+ 357.1314, found 357.1311.
Reference: [1] Organic Letters, 2016, vol. 18, # 19, p. 5166 - 5169
[2] Chemistry - A European Journal, 2011, vol. 17, # 49, p. 13877 - 13882
[3] Green Chemistry, 2017, vol. 19, # 19, p. 4538 - 4543
[4] Journal of Organic Chemistry, 2010, vol. 75, # 19, p. 6549 - 6562
[5] Journal of the American Chemical Society, 2013, vol. 135, # 17, p. 6415 - 6418
[6] Patent: WO2015/138563, 2015, A1, . Location in patent: Page/Page column 24
[7] Patent: US2002/128290, 2002, A1,
[8] Patent: US6514996, 2003, B2,
[9] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 23, p. 10049 - 10060
[10] Journal of the American Chemical Society, 2013, vol. 135, # 17, p. 6415 - 6418
[11] Patent: US2014/235838, 2014, A1, . Location in patent: Paragraph 0068
  • 28
  • [ 105-39-5 ]
  • [ 90-05-1 ]
  • [ 13078-21-2 ]
Reference: [1] Chemische Berichte, 1894, vol. 27, p. 2799
[2] Collection of Czechoslovak Chemical Communications, 1961, vol. 26, p. 902 - 906
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 251 - 254
[4] Journal of the Indian Chemical Society, 1986, vol. 63, p. 317 - 319
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4428 - 4433
[6] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2526 - 2530
[7] Biomacromolecules, 2016, vol. 17, # 6, p. 1921 - 1929
[8] Green Chemistry, 2018, vol. 20, # 16, p. 3761 - 3771
  • 29
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  • [ 4136-26-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1985, vol. 22, # 2, p. 363 - 368
  • 30
  • [ 90-05-1 ]
  • [ 10535-17-8 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1960, p. 1403 - 1404[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1960, # 8, p. 1511 - 1512
[3] Green Chemistry, 2016, vol. 18, # 23, p. 6229 - 6235
[4] Green Chemistry, 2016, vol. 18, # 23, p. 6229 - 6235
[5] Green Chemistry, 2016, vol. 18, # 23, p. 6229 - 6235
[6] Green Chemistry, 2018, vol. 20, # 16, p. 3761 - 3771
  • 31
  • [ 225793-15-7 ]
  • [ 292638-84-7 ]
  • [ 700-44-7 ]
  • [ 24677-78-9 ]
  • [ 90-05-1 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1376 - 1389
  • 32
  • [ 90-05-1 ]
  • [ 75-36-5 ]
  • [ 6100-74-9 ]
Reference: [1] Helvetica Chimica Acta, 1927, vol. 10, p. 389
  • 33
  • [ 90-05-1 ]
  • [ 6100-74-9 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1896
  • 34
  • [ 64-19-7 ]
  • [ 90-05-1 ]
  • [ 6100-74-9 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 280,291
  • 35
  • [ 64-19-7 ]
  • [ 90-05-1 ]
  • [ 10025-87-3 ]
  • [ 6100-74-9 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 280,291
  • 36
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
YieldReaction ConditionsOperation in experiment
95% With tetra-N-butylammonium tribromide In dichloromethane at 23℃; for 2 h; General procedure: A solution of NBu4Br3 (1.0 eq) in CH2Cl2 (~5 mL per mmol NBu4Br3) was added immediately to a solution of a phenole 1 (1.0 eq) in CH2Cl2 (~ 5 mL per mmol 1). The reaction mixture was stirred at 23 °C for 2 h. The solvent was removed under reduced pressure (12 mbar, 40 °C). Water (5.0 mL) was added to the residue and the aqueous layer was extracted with Et2O (3 * 10 mL). The organic layer was separated and dried (MgSO4). The organic solvent was removed under reduced pressure (14 mbar, 40 °C) to leave an oily residue, which was purified by adsorption chromatography (SiO2, CH2Cl2).
95% With N-Bromosuccinimide In acetonitrile for 0.5 h; N-Bromosuccin I self-imide (180 mg, 1 mmol)Add to guaiac acid (124 mg, 1 mmol, Structure 1)In acetonitrile (20 mL);After stirring for 30 minutes, the reaction was quenched with saturated sodium thiosulfate solution,Ethyl acetate extraction three times; the combined organic phase, washed with saturated saline,Drying over anhydrous sodium sulfate and removal of the solvent under reduced pressure give the crude product,Column chromatography (ethyl acetate: petroleum ether, 10: 1),The product 4-bromo-2-methoxyphenol was obtained in a yield of 95percent.
91% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 0.5 h; Inert atmosphere To a stirred solution of 2-methoxyphenol (5.00 g, 40 mmol) in DMF (25 mL) under an atmosphere of nitrogen at 0 °C, was added a solution of N-bromosuccinimide (7.2 g, 40 mmol) in DMF (25 mL). The resulting mixture was stirred for 30 min. Ice cold water (50 mL) was added and the mixture was warmed to room temperature. The aqueous mixture was extracted with diethyl ether (3 * 30 mL) and the combined organic extracts were washed with water (50 mL), brine (50 mL) and then dried (Na2SO4). The crude product was purified by flash chromatography (3:1 hexanes/ethyl acetate) to give the title product 8 (7.41 g, 91percent) as a yellow oil. 1H NMR (300 MHz; CDCl3) 3.87 (3H, s, 2-OCH3), 5.70 (1H, br s, OH), 6.78 (1H, d, J = 6.2 Hz, 6-H), 6.98 (2H, m, 2 * Ar-H); 13C NMR (75 MHz; CDCl3) 56.2 (OCH3), 111.5 (C-4), 114.1, 115.7 and 124.1 (Ar-CH), 144.8 (C-1), 147.2 (C-2). The 1H and 13C NMR data were in agreement with the literature values
78% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 0.5 h; A solution of NBS (1 eq.) in DMF (50mL) was added dropwise to a solution of guaiacol (1eq.) in DMF (50mL) at 0°C. After being stirred for 30min, the reaction mixture was quenched with ice water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and then evaporated to dryness under reduced pressure. The residue was further purified by column chromatography over Silica Gel 200–300N (petroleum ether/ethyl acetate 9.5:0.5) to give 10a as an oil (78percent).

Reference: [1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[2] Tetrahedron, 2014, vol. 71, # 1, p. 91 - 101
[3] Tetrahedron Letters, 1995, vol. 36, # 10, p. 1705 - 1708
[4] Synlett, 2012, vol. 23, # 7, p. 1082 - 1084
[5] Journal of the Serbian Chemical Society, 2011, vol. 76, # 5, p. 685 - 692
[6] Canadian Journal of Chemistry, 1989, vol. 67, p. 2061 - 2066
[7] Tetrahedron, 2012, vol. 68, # 46, p. 9456 - 9463
[8] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7300 - 7314
[9] Patent: CN107325031, 2017, A, . Location in patent: Paragraph 0041-0043
[10] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 11, p. 2542 - 2545
[11] European Journal of Medicinal Chemistry, 2013, vol. 60, p. 240 - 248
[12] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 11, p. 4187 - 4189
[13] Advanced Synthesis and Catalysis, 2004, vol. 346, # 1, p. 77 - 82
[14] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7404 - 7410
[15] European Journal of Organic Chemistry, 2016, vol. 2016, # 12, p. 2177 - 2186
[16] Bioscience, biotechnology, and biochemistry, 2001, vol. 65, # 5, p. 1134 - 1140
[17] Tetrahedron, 2006, vol. 62, # 4, p. 594 - 604
[18] Journal of Natural Products, 2014, vol. 77, # 12, p. 2585 - 2589
[19] Tetrahedron Letters, 2007, vol. 48, # 7, p. 1255 - 1259
[20] Angewandte Chemie - International Edition, 2009, vol. 48, # 43, p. 7996 - 8000
[21] Tetrahedron, 2010, vol. 66, # 34, p. 6928 - 6935
[22] Organic Letters, 2011, vol. 13, # 12, p. 3126 - 3129
[23] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 192 - 202
[24] Synthetic Communications, 2007, vol. 37, # 8, p. 1381 - 1388
[25] Patent: DE105052, , ,
[26] Journal of the American Chemical Society, 1946, vol. 68, p. 1913,1916
[27] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1594,1597; engl. Ausg. S. 1635, 1637
[28] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 159,166
[29] Journal of the Chemical Society, 1908, vol. 93, p. 789
[30] Journal of the American Chemical Society, 1974, vol. 96, # 25, p. 7761 - 7764
[31] Bollettino chimico farmaceutico, 1965, vol. 104, # 11, p. 730 - 734
[32] Tetrahedron, 1990, vol. 46, # 24, p. 8043 - 8052
[33] Canadian Journal of Chemistry, 1982, vol. 60, p. 2099 - 2103
[34] Journal of Organic Chemistry, 2002, vol. 67, # 9, p. 2954 - 2959
[35] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6493 - 6502
  • 37
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 28165-49-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 15, p. 1877 - 1878
[2] Synlett, 1997, vol. 1997, # 11, p. 1241 - 1242
[3] Synlett, 1997, vol. 1997, # 11, p. 1241 - 1242
[4] Tetrahedron Letters, 2007, vol. 48, # 36, p. 6401 - 6404
[5] Tetrahedron, 2010, vol. 66, # 34, p. 6928 - 6935
[6] Tetrahedron, 2012, vol. 68, # 46, p. 9456 - 9463
  • 38
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 53948-36-0 ]
Reference: [1] Journal fuer Praktische Chemie - Practical Applications and Applied Chemistry (Germany), 1999, vol. 341, # 1, p. 59 - 61
  • 39
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 37942-01-1 ]
Reference: [1] Synthesis, 2010, # 10, p. 1629 - 1632
[2] Synthesis, 2010, # 10, p. 1629 - 1632
  • 40
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 28165-49-3 ]
  • [ 53948-36-0 ]
Reference: [1] Dalton Transactions, 2013, vol. 42, # 33, p. 11926 - 11940
  • 41
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 37942-01-1 ]
  • [ 53948-36-0 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
[2] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
  • 42
  • [ 90-05-1 ]
  • [ 2859-78-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 159,166
  • 43
  • [ 79-03-8 ]
  • [ 90-05-1 ]
  • [ 1835-14-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1848 - 1850
[2] Comptes Rendus Chimie, 2013, vol. 16, # 7, p. 660 - 664
  • 44
  • [ 90-05-1 ]
  • [ 1835-14-9 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 60,62
[2] Patent: WO2013/97773, 2013, A1,
  • 45
  • [ 802294-64-0 ]
  • [ 90-05-1 ]
  • [ 1835-14-9 ]
Reference: [1] Yakugaku Zasshi, 1954, vol. 74, p. 836[2] Chem.Abstr., 1955, p. 9556
[3] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 319,332
[4] Journal of Organic Chemistry, 1950, vol. 15, p. 227,229
  • 46
  • [ 90-05-1 ]
  • [ 1835-02-5 ]
Reference: [1] Synthetic Communications, 2014, vol. 44, # 15, p. 2232 - 2238
  • 47
  • [ 90-05-1 ]
  • [ 63057-72-7 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 1913,1916
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 12, p. 2177 - 2186
  • 48
  • [ 507-40-4 ]
  • [ 90-05-1 ]
  • [ 3743-23-5 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2723
  • 49
  • [ 90-05-1 ]
  • [ 3743-23-5 ]
Reference: [1] Gazzetta Chimica Italiana, 1898, vol. 28 I, p. 226
  • 50
  • [ 56-23-5 ]
  • [ 507-40-4 ]
  • [ 90-05-1 ]
  • [ 3743-23-5 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2423
  • 51
  • [ 90-05-1 ]
  • [ 99-40-1 ]
Reference: [1] Chemische Berichte, 1913, vol. 46, p. 4019
  • 52
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 90-05-1 ]
  • [ 617-05-0 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2877 - 2881
  • 53
  • [ 90-05-1 ]
  • [ 617-05-0 ]
Reference: [1] Journal of Organic Chemistry, 1972, vol. 37, p. 3160 - 3163
  • 54
  • [ 92409-34-2 ]
  • [ 6766-82-1 ]
  • [ 20736-25-8 ]
  • [ 90-05-1 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 8, p. 1895 - 1903
  • 55
  • [ 92409-34-2 ]
  • [ 7429-44-9 ]
  • [ 20736-25-8 ]
  • [ 90-05-1 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 8, p. 1895 - 1903
  • 56
  • [ 92409-34-2 ]
  • [ 6766-82-1 ]
  • [ 7429-44-9 ]
  • [ 20736-25-8 ]
  • [ 90-05-1 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 8, p. 1895 - 1903
  • 57
  • [ 87199-16-4 ]
  • [ 90-05-1 ]
  • [ 66855-92-3 ]
YieldReaction ConditionsOperation in experiment
23% With pyridine; copper diacetate In dichloromethane at 20℃; Molecular sieve a) 3-(2-methoxyphenoxy)benzaldehyde(3-Formylphenyl)boronic acid (5.0 g, 33 mmol) and guaiacol (2.8 g, 22 mmol) were mixed with Cu(OAc)2 (4.0 g, 22 mmol), 4A molecular sieves and pyridine (9 mL) in dry EPO <DP n="26"/>dichloromethane (150 mL) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered and concentrated. Column cromatography on SiO2 gave the title compound as an oil (1.7 g, 23percent).1R NMR (400 MHz, CDCB) δ 9.95 (s, IH), 7.58-7.54 (m, IH), 7.47 (t, J= 7.S Hz, IH), 7.38-7.34 (m, IH), 7.26-7.19 (m, 2H), 7.08-7.02 (m, 2H), 7.01-6.95 (m, IH), 3.82 (s, 3H)GC-MS m/z: 228.0 [M]
23% With pyridine; copper diacetate In dichloromethane at 20℃; Molecular sieve a) 3-(2-methoxyphenoxy)benzaldehyde(3-Formylphenyl)boronic acid (5.0 g, 33 mmol) and guaiacol (2.8 g, 22 mmol) were mixed with Cu(OAc)2 (4.0 g, 22 mmol), 4A molecular sieves and pyridine (9 mL) in dry dichloromethane (150 mL) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered and concentrated. Column cromatography on SiO2 gave the title compound as an oil (1.7 g, 23percent).1H NMR (400 MHz, CDC13) δ 9.95 (s, IH), 7.58-7.54 (m, IH), 7.47 (t, J= 7.8 Hz, IH), 7.38-7.34 (m, IH), 7.26-7.19 (m, 2H), 7.08-7.02 (m, 2H), 7.01-6.95 (m, IH), 3.82 (s, 3H)GC-MS m/z: 228.0 [M]
23% With pyridine; copper diacetate In dichloromethane at 20℃; Molecular sieve a) 3-(2-methoxyphenoxy)benzaldehyde(3-Formylphenyl)boronic acid (5.0 g, 33 mmol) and guaiacol (2.8 g, 22 mmol) were mixed with Cu(OAc)2 (4.0 g, 22 mmol), 4A molecular sieves and pyridine (9 mL) in dry EPO <DP n="26"/>dichloromethane (150 mL) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was filtered and concentrated. Column cromatography on SiO2 gave the title compound as an oil (1.7 g, 23percent).1H NMR (400 MHz, CDCB) δ 9.95 (s, IH), 7.58-7.54 (m, IH), 7.47 (t, J= 7.8 Hz, IH), 7.38-7.34 (m, IH), 7.26-7.19 (m, 2H), 7.08-7.02 (m, 2H), 7.01-6.95 (m, IH), 3.82 (s, 3H)GC-MS m/z: 228.0 [M]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 9, p. 2669 - 2672
[2] Patent: WO2006/107252, 2006, A1, . Location in patent: Page/Page column 24-25
[3] Patent: WO2006/107253, 2006, A1, . Location in patent: Page/Page column 29
[4] Patent: WO2006/107254, 2006, A1, . Location in patent: Page/Page column 24; 25
  • 58
  • [ 90-05-1 ]
  • [ 6280-96-2 ]
Reference: [1] Nippon Kagaku Kaishi, 1932, vol. 53, p. 488,491[2] Chem.Abstr., 1933, p. 276
  • 59
  • [ 90-05-1 ]
  • [ 4920-79-0 ]
Reference: [1] Chemische Berichte, 1878, vol. 11, p. 1463
  • 60
  • [ 298-14-6 ]
  • [ 90-05-1 ]
  • [ 877-22-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 19, p. 9673 - 9679
  • 61
  • [ 90-05-1 ]
  • [ 877-22-5 ]
Reference: [1] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1940, p. 235,237[2] Chem.Abstr., 1942, p. 1032
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1940, p. 421,423[4] Chem.Abstr., 1941, p. 5101
  • 62
  • [ 109-72-8 ]
  • [ 60-29-7 ]
  • [ 90-05-1 ]
  • [ 877-22-5 ]
  • [ 2169-28-0 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 4537
  • 63
  • [ 90-05-1 ]
  • [ 2632-13-5 ]
  • [ 19513-80-5 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 3, p. 702 - 706
[2] Green Chemistry, 2016, vol. 18, # 24, p. 6545 - 6555
[3] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1218 - 1221
[4] Journal of Organic Chemistry, 2014, vol. 79, # 22, p. 11091 - 11100
[5] Organic Letters, 2016, vol. 18, # 19, p. 5166 - 5169
[6] Green Chemistry, 2016, vol. 18, # 7, p. 2029 - 2036
[7] Green Chemistry, 2016, vol. 18, # 23, p. 6229 - 6235
[8] Journal of Catalysis, 2017, vol. 346, p. 170 - 179
[9] Green Chemistry, 2017, vol. 19, # 19, p. 4538 - 4543
  • 64
  • [ 90-05-1 ]
  • [ 19513-80-5 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 23, p. 6229 - 6235
[2] Green Chemistry, 2016, vol. 18, # 23, p. 6229 - 6235
  • 65
  • [ 90-05-1 ]
  • [ 28165-49-3 ]
Reference: [1] Synthesis, 2001, # 5, p. 741 - 744
[2] Journal of Organic Chemistry, 1993, vol. 58, # 15, p. 3877 - 3885
[3] Synlett, 2012, vol. 23, # 8, p. 1230 - 1234
[4] Organic Letters, 2011, vol. 13, # 5, p. 960 - 963
[5] Synthesis, 1999, # 7, p. 1127 - 1134
[6] Angewandte Chemie - International Edition, 2017, vol. 56, # 38, p. 11450 - 11455[7] Angew. Chem., 2017, vol. 129, p. 11608 - 11613,6
[8] Tetrahedron, 1996, vol. 52, # 33, p. 10935 - 10944
[9] Australian Journal of Chemistry, 2010, vol. 63, # 10, p. 1437 - 1447
  • 66
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 28165-49-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 15, p. 1877 - 1878
[2] Synlett, 1997, vol. 1997, # 11, p. 1241 - 1242
[3] Synlett, 1997, vol. 1997, # 11, p. 1241 - 1242
[4] Tetrahedron Letters, 2007, vol. 48, # 36, p. 6401 - 6404
[5] Tetrahedron, 2010, vol. 66, # 34, p. 6928 - 6935
[6] Tetrahedron, 2012, vol. 68, # 46, p. 9456 - 9463
  • 67
  • [ 90-05-1 ]
  • [ 28165-49-3 ]
  • [ 37942-01-1 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 36, p. 6413 - 6414
  • 68
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 28165-49-3 ]
  • [ 53948-36-0 ]
Reference: [1] Dalton Transactions, 2013, vol. 42, # 33, p. 11926 - 11940
  • 69
  • [ 90-05-1 ]
  • [ 15969-08-1 ]
Reference: [1] Chemische Berichte, 1906, vol. 39, p. 2725
[2] Journal of Medicinal Chemistry, 1986, vol. 29, # 4, p. 538 - 549
[3] Patent: US4965261, 1990, A,
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2928 - 2932
[5] Patent: US2007/10670, 2007, A1, . Location in patent: Page/Page column 104
[6] Patent: US2008/64871, 2008, A1, . Location in patent: Page/Page column 67
  • 70
  • [ 90-05-1 ]
  • [ 20734-71-8 ]
  • [ 15969-08-1 ]
YieldReaction ConditionsOperation in experiment
29% With nitric acid In dichloromethane at -20 - 20℃; for 2 h; Fuming HNO3 (0.34 mL, 0.008 mmol) was carefully added to a mixture of 2-methoxyphenol (0.886 mL, 0.008 mmol) in anhydrous DCM (10 mL) at -20° C. After stirring for 2 h at RT, the mixture was concentrated under vacuum. Chromatography (10-30percent EtOAc/hexanes) provided 9A12 (400 mg, 29percent) and 2-methoxy-3-nitrophenol (400 mg, 29percent).
Reference: [1] Patent: US2007/93477, 2007, A1, . Location in patent: Page/Page column 27
  • 71
  • [ 90-05-1 ]
  • [ 3251-56-7 ]
  • [ 15969-08-1 ]
Reference: [1] Synthetic Communications, 2003, vol. 33, # 6, p. 961 - 966
[2] Tetrahedron, 1998, vol. 54, # 27, p. 7843 - 7848
[3] Tetrahedron, 1990, vol. 46, # 7, p. 2661 - 2674
[4] Monatshefte fuer Chemie, 1912, vol. 33, p. 706
[5] South African Journal of Chemistry, 2006, vol. 59, p. 93 - 96
  • 72
  • [ 110-71-4 ]
  • [ 60-29-7 ]
  • [ 90-05-1 ]
  • [ 15969-08-1 ]
Reference: [1] Patent: US2008/305169, 2008, A1,
  • 73
  • [ 90-05-1 ]
  • [ 3251-56-7 ]
  • [ 636-93-1 ]
  • [ 20734-71-8 ]
  • [ 15969-08-1 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 1277 - 1279
  • 74
  • [ 90-05-1 ]
  • [ 3251-56-7 ]
  • [ 636-93-1 ]
  • [ 15969-08-1 ]
  • [ 107112-04-9 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 1277 - 1279
  • 75
  • [ 90-05-1 ]
  • [ 3251-56-7 ]
  • [ 4097-63-6 ]
  • [ 15969-08-1 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 7, p. 1201 - 1208
  • 76
  • [ 64-19-7 ]
  • [ 90-05-1 ]
  • [ 15969-08-1 ]
Reference: [1] Chemische Berichte, 1906, vol. 39, p. 2725
  • 77
  • [ 7697-37-2 ]
  • [ 64-19-7 ]
  • [ 90-05-1 ]
  • [ 4097-63-6 ]
  • [ 15969-08-1 ]
Reference: [1] Chem. Zentralbl., 1898, vol. 69, # II, p. 1169
[2] Monatshefte fuer Chemie, 1912, vol. 33, p. 706
  • 78
  • [ 60-29-7 ]
  • [ 7697-37-2 ]
  • [ 90-05-1 ]
  • [ 3251-56-7 ]
  • [ 4097-63-6 ]
  • [ 15969-08-1 ]
Reference: [1] Monatshefte fuer Chemie, 1912, vol. 33, p. 706
  • 79
  • [ 90-05-1 ]
  • [ 92409-34-2 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 17, p. 6415 - 6418
[2] Green Chemistry, 2018, vol. 20, # 16, p. 3761 - 3771
  • 80
  • [ 90-05-1 ]
  • [ 52200-90-5 ]
Reference: [1] Chem. Zentralbl., 1907, vol. 78, # II, p. 2044
[2] Journal of the American Chemical Society, 1919, vol. 41, p. 460
  • 81
  • [ 90-05-1 ]
  • [ 121-57-3 ]
  • [ 52200-90-5 ]
Reference: [1] Chemische Berichte, 1897, vol. 30, p. 2444
  • 82
  • [ 90-05-1 ]
  • [ 96-24-2 ]
  • [ 93-14-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5071 - 5078
[2] Tetrahedron Asymmetry, 2006, vol. 17, # 21, p. 3015 - 3020
[3] Journal of the Chemical Society, 1912, vol. 101, p. 309
[4] Chimica Therapeutica, 1969, vol. 4, p. 200 - 206
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 3, p. 508 - 525
[6] Patent: WO2013/167988, 2013, A1, . Location in patent: Paragraph 0093; 0094; 0099
[7] Patent: US2015/133533, 2015, A1, . Location in patent: Paragraph 0113
  • 83
  • [ 616-30-8 ]
  • [ 90-05-1 ]
  • [ 93-14-1 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: at 50℃; for 3 h; Reflux
Stage #2: at 90℃; for 5 h;
Equipped with a stirrer, a thermometer, a reflux condenser, a reaction vessel, 1.5mol sodium sulfite was added, the mass fraction of 20percent potassium chloride solution 300ml, controlling the stirring speed of 160 rpm, was slowly added guaiacol (2) 1.3mol, solution temperature rises to 50 , holding 3h, was added 3-amine 1,2-propanediol (3) 1.7mol, increasing the solution temperature 90 , maintained under stirring 5h, the temperature of the solution is reduced to 15 , allowed to stand for 25h after removing the aqueous layer delamination, the mass fraction of oil was added 200ml of 25percent solution of sodium bromide, mass fraction of 35percent oxalic acid solution was adjusted to maintain the pH at 7, after cooling the precipitated solid was suction filtered, washed with a solution of potassium nitrate, mass fraction washed with 70percent nitro methane in the mass fraction of 98percent propylene eye recrystallized to give crystals of 3- (o-methoxyphenoxy) -1,2-propanediol 185.33g, yield 72percent.
Reference: [1] Patent: CN105566073, 2016, A, . Location in patent: Paragraph 0013; 0014
  • 84
  • [ 556-52-5 ]
  • [ 90-05-1 ]
  • [ 14007-09-1 ]
  • [ 93-14-1 ]
YieldReaction ConditionsOperation in experiment
95% With calcined hydrotalcite In tetrahydrofuran at 120℃; for 4 h; Autoclave In a typical reaction, autoclave reactor (details included in sup-porting information) was charged with guaiacol (0.0081 mol), gly-cidol (0.020 mol), tetrahydrofuran (THF) (10 mL) and 0.03 g mL−1(0.9 g) of the catalyst. The total organic phase volume was made to30 mL with THF. An initial sample was taken at the desired temperature. The reaction mixture was stirred with mechanical stirrer atthe desired speed, and samples were collected periodically. For control reaction, speed of agitation was 1000 rpm and temperature was 120°C at self-generated pressure. Reaction samples were analyzed by HPLC (details included in supporting information). Synthesis of guaifenesin (3-(2-methoxyphenoxy)propane-1,2-diol) andbyproduct (2-(2-methoxyphenoxy)propane-1,3-diol) from condensation reaction of guaiacol and glycidol is shown in Scheme 1.
Reference: [1] Catalysis Today, 2017, vol. 291, p. 213 - 222
  • 85
  • [ 556-52-5 ]
  • [ 90-05-1 ]
  • [ 93-14-1 ]
Reference: [1] Chirality, 2016, vol. 28, # 4, p. 313 - 318
[2] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[3] Chemical Communications, 2013, vol. 49, # 52, p. 5886 - 5888
[4] Physical Chemistry Chemical Physics, 2017, vol. 19, # 41, p. 28302 - 28312
  • 86
  • [ 90-05-1 ]
  • [ 93-14-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1980, # 22, p. 1053 - 1054
[2] Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 586 - 593
[3] Patent: US4390732, 1983, A,
  • 87
  • [ 90-05-1 ]
  • [ 106-89-8 ]
  • [ 25772-81-0 ]
  • [ 16929-60-5 ]
  • [ 93-14-1 ]
  • [ 2210-74-4 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
  • 88
  • [ 90-05-1 ]
  • [ 56-81-5 ]
  • [ 93-14-1 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 3, p. 625 - 628
  • 89
  • [ 90-05-1 ]
  • [ 95041-90-0 ]
Reference: [1] Synthesis, 2011, # 22, p. 3711 - 3715
  • 90
  • [ 90-05-1 ]
  • [ 95041-90-0 ]
  • [ 117048-62-1 ]
Reference: [1] Synthesis, 2011, # 22, p. 3711 - 3715
[2] Synthesis, 2011, # 22, p. 3711 - 3715
  • 91
  • [ 578-57-4 ]
  • [ 135999-16-5 ]
  • [ 90-05-1 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 15, p. 4291 - 4296
  • 92
  • [ 90-05-1 ]
  • [ 203861-62-5 ]
  • [ 111726-46-6 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 22, p. 2664 - 2667
[2] Letters in Organic Chemistry, 2011, vol. 8, # 4, p. 258 - 263
  • 93
  • [ 90-05-1 ]
  • [ 111726-46-6 ]
Reference: [1] Australian Journal of Chemistry, 1997, vol. 50, # 7, p. 767 - 769
[2] Canadian Journal of Chemistry, 1987, vol. 65, p. 2019 - 2023
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308[4] Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4
[5] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069
  • 94
  • [ 90-05-1 ]
  • [ 160968-99-0 ]
Reference: [1] Patent: WO2011/30356, 2011, A2,
[2] Patent: US2012/165548, 2012, A1,
[3] Patent: WO2011/101864, 2011, A1,
[4] Molecules, 2018, vol. 23, # 9,
  • 95
  • [ 90-05-1 ]
  • [ 85416-73-5 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 20, p. 4907 - 4916
  • 96
  • [ 90-05-1 ]
  • [ 150728-12-4 ]
Reference: [1] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
  • 97
  • [ 90-05-1 ]
  • [ 150728-13-5 ]
Reference: [1] Patent: WO2011/24056, 2011, A2,
[2] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 658 - 670
[3] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
  • 98
  • [ 90-05-1 ]
  • [ 160969-03-9 ]
Reference: [1] Patent: WO2011/101864, 2011, A1,
  • 99
  • [ 1427177-23-8 ]
  • [ 90-05-1 ]
  • [ 95635-55-5 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 3, p. 756 - 767
[2] RSC Advances, 2016, vol. 6, # 54, p. 49150 - 49157
  • 100
  • [ 90-05-1 ]
  • [ 95635-55-5 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 5, p. 748 - 754
[2] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[3] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[4] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[5] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[6] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[7] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[8] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[9] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[10] Patent: US2013/90475, 2013, A1,
[11] Patent: US2013/90475, 2013, A1,
[12] Patent: WO2016/142819, 2016, A2,
  • 101
  • [ 90-05-1 ]
  • [ 151541-15-0 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 17, p. 6415 - 6418
  • 102
  • [ 28868-76-0 ]
  • [ 90-05-1 ]
  • [ 150726-89-9 ]
YieldReaction ConditionsOperation in experiment
78.7% With sodium methylate In methanol at 45℃; for 1 h; A sodiummethoxide solution in methanol (2.3 g of Na, 0.10 mol, 1.0 eq in75 ml of MeOH) was slowly added to a stirred mixture of guaiacole(12.5 g, 0.100 mol, 10 eq) and dimethyl 2-chloromalonate (19.0 g,0.114 mol, 1.14 eq). After having reacted for 1 h at 45 °C, the volatilematerial were evaporated and the residue was taken up in toluene,washed with water and NaHCO3 (1percent aqueous solution). Theconcentrated organic phase afforded 20.0 g (yield 78.7percent) of aviscous oil that was characterized as follows: bp 131 °C (lit. [38] bp128 °C); 1H NMR (CDCl3) δ 7.12-7.00 (m, 2H), 6.98-6.90 (m, 1H),6.90-6.82 (m, 1H), 5.27 (s, 1H), 3.85 (s, 3H), 3.84 (s, 6H); 13C NMR(CDCl3) δ 166.2 (2C), 150.4, 146.0, 124.4, 120.8, 119.0, 112.5, 78.4,55.8, 53.0 (2C); HRMS calcd for C12H14O6 255.0869 (M+H+), found255.0870 (M+H+).
65%
Stage #1: With sodium hydroxide In toluene for 2 h; Reflux; Dean-Stark; Large scale
Stage #2: for 3 h; Reflux; Large scale
Sodium hydroxide (28.27 kg, 706.86 mol) was added in one portion to a mixture of 2-methoxyphenol (13, 75 kg, 604.16 mol) and toluene (525 L) at 20–30C under stirring.The reaction mixture was heated to reflux temperature and the water was separated azeotropically using a Dean-Stark trap for 2 h. Then dimethyl chloromalonate (12,110.69 kg, 664.57 mol) was added to the reaction mixture at 60–65C over a period of30 min and heated to reflux and stirred for 3 h. After completion of the reaction, the mixturewas cooled to 20–30C and diluted with de-mineralized water (150 L). The twolayers were separated, and the organic layer was washed with 1percent w/v aqueous sodiumhydroxide (2 £ 150 L). The organic layer was separated and concentrated to give oilymass which was dissolved in methyl tert-butyl ether (225 L) at 20–30C; then n-heptane(60 L) was cautiously added over 45 min at 20–30C. The resulting solution was seededwith crystals of compound 1 (0.075 kg) to induce crystallization, then stirred for 1 h,cooled to 10C and stirred for 2 h at the same temperature. Then the solid formed wascollected and dried at 30C under reduced pressure to afford 99.10 kg (65percent yield) of 1 ascolorless crystals, mp: 38–40C, (purity of 95.13percent a/a). 1H NMR (CDCl3, 300 MHz): d7.02–7.06 (m, 2H), 6.84–6.93 (m, 2H) 5.26 (s, 1H), 3.85 (s, 9H). MS M/z (ESI): 253.0[(MCH)].
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 658 - 670
[2] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
[3] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 4, p. 897 - 907
[4] Patent: US5292740, 1994, A,
[5] Patent: WO2011/24056, 2011, A2, . Location in patent: Page/Page column 19
  • 103
  • [ 90-05-1 ]
  • [ 150727-06-3 ]
Reference: [1] Patent: WO2011/24056, 2011, A2,
[2] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 658 - 670
[3] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
  • 104
  • [ 90-05-1 ]
  • [ 94687-10-2 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 17, p. 6415 - 6418
[2] Patent: WO2015/138563, 2015, A1,
[3] Green Chemistry, 2018, vol. 20, # 16, p. 3761 - 3771
  • 105
  • [ 90-05-1 ]
  • [ 92409-15-9 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 24, p. 6545 - 6555
[2] Green Chemistry, 2018, vol. 20, # 16, p. 3761 - 3771
  • 106
  • [ 90-05-1 ]
  • [ 92409-23-9 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 19, p. 5166 - 5169
[2] Green Chemistry, 2016, vol. 18, # 24, p. 6545 - 6555
  • 107
  • [ 90-05-1 ]
  • [ 2632-13-5 ]
  • [ 92409-23-9 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1218 - 1221
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