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Product Citations

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Jooste, Joelien ; Legoabe, Lesetja J ; Ilbeigi, Kayhan , et al. DOI: PubMed ID:

Abstract: Geraniol, a primary component of several essential oils, has been associated with broad-spectrum antiprotozoal activities, although moderate to weak. This study primarily concentrated on the synthesis of hydrazinated geraniol derivatives aspotential antiprotozoal agents. The synthesised compounds were tested in vitro against different parasitic protozoans of clinical relevance, including Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense, Trypanosoma cruzi and Leishmania infantum. Compounds 6, 8, 13, 14 and 15 demonstrated low micromolar activity against the different parasites. Compounds 8, 13, 14 and 15 had the highest efficacy against Trypanosoma brucei rhodesiense, as indicated by their respective IC50 values of 0.74, 0.56, 1.26 and 1.00 μM. Compounds 6, 14 and 15 displayed the best activity against Trypanosoma brucei brucei, with IC50 values of 1.49, 1.48 and 1.85 μM, respectively. The activity of compounds 6, 14 and 15 also extended to intracellular Trypanosoma cruzi, with IC50 values of 5.14, 6.30 and 4.90 μM, respectively. Compound 6, with an IC50 value of 11.73 μM, and compound 14, with an IC50 value of 8.14 μM, demonstrated some modest antileishmanial activity.

Keywords: geraniol ; Leishmania infantum ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense ; Trypanosoma cruzi

Purchased from AmBeed: ; ; ; ;

Agarwal, Devesh S. ; Beteck, Richard M. ; Ilbeigi, Kayhan , et al. DOI: PubMed ID:

Abstract: A library of imidazo[1,2-a]pyridine-appended chalcones were synthesized and characterized using 1H NMR,13C NMR and HRMS. The synthesized analogs were screened for their antikinetoplastid activity against Trypanosoma cruzi, Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense and Leishmania infantum. The analogs were also tested for their cytotoxicity activity against human lung fibroblasts and primary mouse macrophages. Among all screened derivatives, (E)-N-(4-(3-(2-chlorophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active against T. cruzi and T. b. brucei exhibiting IC50 values of 8.5 and 1.35 μM, resp. Against T. b. rhodesiense, (E)-N-(4-(3-(4-bromophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active with an IC50 value of 1.13 μM. All synthesized active analogs were found to be non-cytotoxic against MRC-5 and PMM with selectivity indexes of up to more than 50.

Keywords: antikinetoplastid ; chalcone ; drug likeliness properties ; imidazo[1,2-a]pyridine ; neglected tropical diseases (NTDs) ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense

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Jan Nowak ; Michał Tryniszewski ; Michał Barbasiewicz DOI:

Abstract: Heteroatom-based olefinating reagents (e.g., organic phosphonates, sulfonates, etc.) are used to transform carbonyl compounds into alkenes, and their mechanism of action involves aldol-type addition, cyclization, and fragmentation of four-membered ring intermediates. We have developed an analogous process using ethyl 1,1,1,3,3,3-hexafluoroisopropyl methylmalonate, which converts electrophilic aryl aldehydes into α-methylcinnamates in up to 70% yield. The reaction plausibly proceeds through the formation of β-lactone that spontaneously decarboxylates under the reaction conditions. The results shed light on the Knoevenagel–Doebner olefination, for which decarboxylative anti-fragmentation of aldol-type adducts is usually considered.

Keywords: olefination ; carbonyl compounds ; reaction mechanism ; lactones ; malonates ; Knoevenagel ; Doebner reaction

Purchased from AmBeed: ; ; ; ; ; ;

Dylan Hart ; Lesetja J. Legoabe ; Omobolanle J. Jesumoroti , et al. DOI: PubMed ID:

Abstract: Herein we report the synthesis of novel compounds inspired by the antimicrobial activities of nitroazole and thiazolidin-4-one based compounds reported in the literature. Target compounds were investigated in vitro for antitubercular, antibacterial, antifungal, and overt cell toxicity properties. All compounds exhibited potent antitubercular activity. Most compounds exhibited low micromolar activity against S. aureus and C. albicans with no overt cell toxicity against HEK-293 cells nor haemolysis against human red blood cells. Notably, compound 3b exhibited low to sub-micromolar activities against Mtb, MRSA, and C. albicans. 3b showed superior activity (0.25 μg/ml) against MRSA compared to vancomycin (1 μg/ml).

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; 591-31-1 ; ; ; ; ; ; 123-08-0 ; 100-52-7 ; ; 89-98-5

Product Details of [ 587-04-2 ]

CAS No. :587-04-2 MDL No. :MFCD00003350
Formula : C7H5ClO Boiling Point : -
Linear Structure Formula :- InChI Key :SRWILAKSARHZPR-UHFFFAOYSA-N
M.W : 140.57 Pubchem ID :11477
Synonyms :

Calculated chemistry of [ 587-04-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.84
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 2.26
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.14

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.385 mg/ml ; 0.00274 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 0.782 mg/ml ; 0.00556 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.163 mg/ml ; 0.00116 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 587-04-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 587-04-2 ]

* 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 [ 587-04-2 ]
  • Downstream synthetic route of [ 587-04-2 ]

[ 587-04-2 ] Synthesis Path-Upstream   1~48

  • 1
  • [ 587-04-2 ]
  • [ 22483-09-6 ]
  • [ 34784-06-0 ]
  • [ 34784-07-1 ]
Reference: [1] Patent: US2007/254879, 2007, A1, . Location in patent: Page/Page column 29; 30
  • 2
  • [ 587-04-2 ]
  • [ 34784-06-0 ]
Reference: [1] Canadian Journal of Research, Section B: Chemical Sciences, 1949, vol. 27, p. 161,166
  • 3
  • [ 587-04-2 ]
  • [ 22483-09-6 ]
  • [ 34784-06-0 ]
  • [ 34784-07-1 ]
Reference: [1] Patent: US2007/254879, 2007, A1, . Location in patent: Page/Page column 29; 30
  • 4
  • [ 587-04-2 ]
  • [ 5430-45-5 ]
Reference: [1] Canadian Journal of Research, Section B: Chemical Sciences, 1949, vol. 27, p. 161,166
  • 5
  • [ 587-04-2 ]
  • [ 70057-67-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5735 - 5738
[2] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 5, p. 611 - 618
[3] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 843 - 851
[4] Catalysis Letters, 2018, vol. 148, # 11, p. 3486 - 3491
  • 6
  • [ 587-04-2 ]
  • [ 937-14-4 ]
Reference: [1] Catalysis Letters, 2016, vol. 146, # 10, p. 2157 - 2164
  • 7
  • [ 587-04-2 ]
  • [ 766-80-3 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 28, p. 3692 - 3694
[2] MedChemComm, 2015, vol. 6, # 6, p. 1104 - 1116
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 561 - 569
[4] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 790 - 804
[5] Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063
[6] Chinese Chemical Letters, 2016, vol. 27, # 2, p. 295 - 301
  • 8
  • [ 587-04-2 ]
  • [ 873-63-2 ]
  • [ 4152-90-3 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 12, p. 2055 - 2058
  • 9
  • [ 540-69-2 ]
  • [ 587-04-2 ]
  • [ 4152-90-3 ]
Reference: [1] Journal of the Karnatak University, 1957, vol. 2, p. 19,26
  • 10
  • [ 587-04-2 ]
  • [ 13078-79-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 1983, vol. 18, # 4, p. 319 - 329
  • 11
  • [ 587-04-2 ]
  • [ 7094-34-0 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 7, p. 2161 - 2163
  • 12
  • [ 587-04-2 ]
  • [ 7094-34-0 ]
  • [ 2050-67-1 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 7, p. 2161 - 2163
  • 13
  • [ 108-37-2 ]
  • [ 587-04-2 ]
  • [ 7094-34-0 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 6, p. 1648 - 1656
  • 14
  • [ 587-04-2 ]
  • [ 6361-23-5 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 888 - 896
  • 15
  • [ 587-04-2 ]
  • [ 6628-86-0 ]
YieldReaction ConditionsOperation in experiment
60.6% at -20 - -10℃; for 0.5 h; Step A: 5-ch.oro-2-nitrobenzaidehyde 3-Ch.orobenzaldehyde (15 g, 107 mmo.) was added to concentrated sulfuric acid (150 mL) at -20 °C, followed by addition of potassium nitrate (1 1 .9 g, 1 17 mmoi) in portions, keeping the temperature bellow -10 °C. After addition, the mixture was stirred for 30 minutes and then poured into ice-water. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed by brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 5-chioro-2-nitrobenza.dehyde (12.0 g, yield 60.6 percent).
Reference: [1] Chemical Communications, 2011, vol. 47, # 36, p. 10133 - 10135
[2] Tetrahedron, 2010, vol. 66, # 38, p. 7544 - 7561
[3] Patent: WO2012/92880, 2012, A1, . Location in patent: Page/Page column 49-50
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 146
[5] Justus Liebigs Annalen der Chemie, 1891, vol. 262, p. 149[6] Zeitschrift fuer Kristallographie, Kristallgeometrie, Kristallphysik, Kristallchemie, 1894, vol. 23, p. 470
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 143
[8] Journal of Organic Chemistry, 1960, vol. 25, p. 1542 - 1547
[9] Patent: US4415572, 1983, A,
[10] Organic Letters, 2008, vol. 10, # 2, p. 173 - 175
[11] Journal of Organic Chemistry, 2008, vol. 73, # 21, p. 8608 - 8611
[12] Chinese Journal of Chemistry, 2012, vol. 30, # 7, p. 1571 - 1574
[13] European Journal of Organic Chemistry, 2014, vol. 2014, # 26, p. 5827 - 5835,9
[14] Patent: CN103467300, 2016, B,
[15] Patent: DE30329, , ,
[16] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 146
  • 16
  • [ 587-04-2 ]
  • [ 21640-48-2 ]
  • [ 1866-38-2 ]
Reference: [1] Patent: US4073911, 1978, A,
  • 17
  • [ 587-04-2 ]
  • [ 321-31-3 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 33, p. 4483 - 4486
[2] Chemical Communications, 2018, vol. 54, # 78, p. 11017 - 11020
  • 18
  • [ 587-04-2 ]
  • [ 98-80-6 ]
  • [ 63012-03-3 ]
YieldReaction ConditionsOperation in experiment
75% With bis(acetylacetonate)nickel(II); potassium carbonate In toluene at 180℃; for 0.166667 h; Microwave irradiation Aldehyde (1.0 mmol), arylboronic acid (1.5 mmol, 1.5 equiv), K2CO3 (138 mg, 1.0 mmol, 1 equiv), and Ni(acac)2 (2.6 mg, 0.01 mmol, 1 mol percent) were added to a 10 mL microwave processing vial containing a Teflon coated stir bar. After the vial was sealed dry toluene (2 mL) was transferred to the vial and mixture was pre-stirred for 5 min. The vial was placed in the microwave cavity and heated for 10 min at 180 °C (fixed hold time). After cooling, diethyl ether or ethyl acetate (10 mL) was added and the crude reaction mixture was subsequently washed with 25percent aqueous NH3 (2 .x. 10 mL). The aqueous ammonium layer was reextracted again with diethyl ether or ethyl acetate (2 .x. 10 mL). The combined organic phase was dried over MgSO4 and the residue after evaporation purified by flash chromatography using a petroleum ether/ethylacetate (10:1-2.5:1) as eluent phase.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 14, p. 1677 - 1679
  • 19
  • [ 108-86-1 ]
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With iodine; magnesium In diethyl ether at 0℃; for 0.166667 h;
Stage #2: for 12 h;
General procedure: A 50 mL round-bottom flask was charged with bromobenzene (157 mg, 1 mmol), anhydrous Et2O (10 mL), magnesium powder (24 mg, 1 mmol) and a little iodine added. The mixture was cooled to 0 °C and stirred for 10 min, then a solution of 3-methoxybenzaldehyde (136 mg, 1 mmol) and anhydrous Et2O was added slowly. The solution was stirred for 12 h after the temperature rose to room temperature; 5 mL NH4Cl aqueous solution was dropped slowly, and the mixture extracted with Et2O (3×30 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was isolated by flash column chromatography on silica gel to give the products.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 13, p. 1747 - 1750
[2] Patent: US5719168, 1998, A,
  • 20
  • [ 3262-89-3 ]
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 6, p. 924 - 927
  • 21
  • [ 1623-99-0 ]
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
YieldReaction ConditionsOperation in experiment
0.160 mol, 91.0% With hydrogenchloride; sodium In chlorobenzene; toluene Example 2
(Preparation of 3-chlorobenzhydrol)
To phenylsodium, prepared from 9.2 g (0.400 mol) of a sodium dispersion and 22.0 g (0.196 mol) of chlorobenzene in 200 g of toluene, was added, dropwise, a solution of 24.8 g (0.176 mol) of 3-chlorobenzaldehyde in toluene (24 g), with the temperature kept at 0 °C to 3 °C.
After stirring at that temperature for 1 hour, hydrolysis with 100 ml of 20percent-diluted hydrochloric acid was carried out, and the obtained organic layer was separated and washed with water three times.
After the solvent was concentrated, the remained pale orange oil was distilled under reduced pressure, to give 34.9 g (0.160 mol, 91.0percent) of the intended product (b.p.: 147.0 to 148.0 °C/2 mmHg).
Reference: [1] Patent: EP801048, 1997, A1,
  • 22
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 6, p. 1648 - 1656
  • 23
  • [ 587-04-2 ]
  • [ 100-58-3 ]
  • [ 63012-03-3 ]
Reference: [1] Green Chemistry, 2009, vol. 11, # 12, p. 1973 - 1978
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1378 - 1383
[3] Chemistry - A European Journal, 2013, vol. 19, # 18, p. 5542 - 5545
  • 24
  • [ 587-04-2 ]
  • [ 63012-03-3 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1925, vol. 56, p. 150[2] Chem. Zentralbl., 1926, vol. 97, # I, p. 919
  • 25
  • [ 90965-06-3 ]
  • [ 587-04-2 ]
  • [ 766-83-6 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 103, p. 59297 - 59301
  • 26
  • [ 587-04-2 ]
  • [ 14123-60-5 ]
Reference: [1] Chimica Therapeutica, 1968, vol. 3, p. 313 - 320
[2] Journal of the American Chemical Society, 1964, vol. 86, p. 684 - 687
  • 27
  • [ 587-04-2 ]
  • [ 34841-35-5 ]
Reference: [1] Journal of Organic Chemistry, 1976, vol. 41, p. 2368 - 2372
[2] Organic Letters, 2015, vol. 17, # 24, p. 6102 - 6105
  • 28
  • [ 64-17-5 ]
  • [ 587-04-2 ]
  • [ 1128-76-3 ]
  • [ 535-80-8 ]
YieldReaction ConditionsOperation in experiment
66% With sodium cyanide In N,N-dimethyl-formamide at 50℃; for 1 h; Molecular sieve General procedure: Aldehyde 1 (1.0 mmol; 1.0 equiv.) and 4 Å molecular sieves (300 mg) were added to a mixture of DMF (3.0 mL) and an appropriate alcohol (or a thiol) (3.0 mL). To the above solution was added sodium cyanide (1.5 mmol; 1.5 equiv). The reaction mixture was stirred in an open flask at 50 C and monitored by TLC. After the complete consumption of 1, the mixture was poured into water (25 mL) and extracted with diethyl ether (5 × 10 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated. The crude mixture was further purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent to furnish the desired ester compound 3. The aqueous layer was acidified with HCl, extracted with ether, and concentrated to yield the corresponding carboxylic acid 6, which was sufficiently pure needing no further purification.
Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 8, p. 2055 - 2061
  • 29
  • [ 64-17-5 ]
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  • [ 1128-76-3 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 6, p. 2070 - 2072
  • 30
  • [ 587-04-2 ]
  • [ 1099-45-2 ]
  • [ 1128-76-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 870 - 878
  • 31
  • [ 141-82-2 ]
  • [ 587-04-2 ]
  • [ 1866-38-2 ]
YieldReaction ConditionsOperation in experiment
90.8% at 85℃; for 6 h; General procedure: To a stirred solution of 6.76 g (65 mmol) malonic acid in pyridine (5 mL) and piperidine (0.5 mL), the corresponding aldehyde (50 mmol) was added slowly under 85 oC. The resulting mixture was stirred for 6 h, when TLC analyses indicated the disappearance of the starting material. After cooling to ambient temperature, the reaction mixture was neutralized with 10percent hydrochloric acid under ice bath, observing crystallization of a white solid, which was filtered and washed three times with cooled waster. Recrystallization from aqueous ethanol (1:1) afforded 2a-h.
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9152 - 9157
[2] Journal of Chemical Research, 2005, # 6, p. 364 - 365
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 7, p. 1849 - 1853
[4] Proceedings - Indian Academy of Sciences, Section A, 1941, vol. 14, p. 116 - 120[5] Chem.Abstr., 1942, p. 1599
[6] Journal of the American Chemical Society, 1947, vol. 69, p. 852
[7] Org. Synth. Coll., 1963, vol. Vol. IV, p. 731,733
[8] Heterocycles, 1994, vol. 37, # 3, p. 1495 - 1502
[9] European Journal of Medicinal Chemistry, 2002, vol. 37, # 12, p. 979 - 984
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[11] Chemical Biology and Drug Design, 2013, vol. 81, # 2, p. 275 - 283
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[14] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7272 - 7276
[15] ChemMedChem, 2018, vol. 13, # 15, p. 1517 - 1529
  • 32
  • [ 64-19-7 ]
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  • [ 1866-38-2 ]
YieldReaction ConditionsOperation in experiment
75% With pyridine; dmap; sodium tetraborate decahydrate; N-benzyl-N,N,N-triethylammonium chloride In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 8 h; General procedure: A 100 mL, round-bottomed flask was charged with Na2B4O7 ·10H2O (5 mmol, 1.9 g) and heated at 160-180°C for 3-4 h untilconstant weight. Benzyl-triethylammonium chloride (5 mmol,1.14 g), DMAP (5 mmol, 0.61 g), Py (20 mmol, 1.61 mL) andNMP (3 mL) were added. This mixture was heated at reflux,under stirring for 2-2.5 h, when benzyltriethylammonium-sodiumtetraborate complex resulted in situ. The solution temperature wasdecreased to 70°C and acetic acid (50 mmol, 2.85 mL), andp-chlorobenzaldehyde (5 mmol, 0.70 g) were added. A condenserwas fitted to the flask and the excess of acetic acid was removedby distillation until the temperature in the flask reached 185-187°C. The obtained solution was finally heated under reflux at185-190°C for 6-10 h (see Table 1). After cooling down, thesolution was treated with water (5-7 mL) and aqueous NaOH(20percent) to pH=9-10, and the unreacted aromatic aldehyde wasdistilled as azeotropic mixture with water, until the distillate wasclear. The final solution was filtered off and the filtrate was treatedwith HCl solution 15-20percent until pH=1-2, under cooling on ice andstirring for 2-3 h, when cinnamic acid precipitated. The resultedproduct was filtered off, washed with cold water (15-20 mL) anddried in a vacuum oven. Recrystallization from aqueous EtOH orEtOAc:petroleum ether gave pure products as white or yellowishcrystals. In all cases, a good trans-selectivity for the cinnamicacids was observed.
Reference: [1] Revue Roumaine de Chimie, 2009, vol. 54, # 11-12, p. 987 - 991
[2] Revue Roumaine de Chimie, 2013, vol. 58, # 2-3, p. 161 - 164
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  • [ 21640-48-2 ]
  • [ 1866-38-2 ]
Reference: [1] Patent: US4073911, 1978, A,
  • 34
  • [ 108-24-7 ]
  • [ 587-04-2 ]
  • [ 1866-38-2 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1999, vol. 33, # 3, p. 158 - 159
[2] Monatshefte fuer Chemie, 1934, vol. 64, p. 399,407
  • 35
  • [ 587-04-2 ]
  • [ 1866-38-2 ]
Reference: [1] Helvetica Chimica Acta, 1920, vol. 3, p. 794
  • 36
  • [ 108-41-8 ]
  • [ 14495-51-3 ]
  • [ 587-04-2 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 22, p. 4562 - 4564
  • 37
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  • [ 39191-07-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118
  • 38
  • [ 593-51-1 ]
  • [ 587-04-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 972 - 986
  • 39
  • [ 587-04-2 ]
  • [ 20028-53-9 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 36, p. 10133 - 10135
  • 40
  • [ 587-04-2 ]
  • [ 39180-82-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118
  • 41
  • [ 587-04-2 ]
  • [ 68208-25-3 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 7, p. 1503 - 1505
  • 42
  • [ 587-04-2 ]
  • [ 52010-98-7 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 5, p. 1278 - 1281
  • 43
  • [ 587-04-2 ]
  • [ 22233-52-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 28, p. 5113 - 5118
  • 44
  • [ 587-04-2 ]
  • [ 80126-51-8 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 46, p. 7256 - 7262
  • 45
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  • [ 25698-37-7 ]
  • [ 119565-00-3 ]
Reference: [1] Synthetic Communications, 1988, vol. 18, # 14, p. 1685 - 1690
  • 46
  • [ 587-04-2 ]
  • [ 73183-34-3 ]
  • [ 380151-86-0 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3543 - 3548
[2] RSC Advances, 2018, vol. 8, # 25, p. 13643 - 13648
  • 47
  • [ 587-04-2 ]
  • [ 174265-12-4 ]
YieldReaction ConditionsOperation in experiment
90.1% at 10 - 25℃; for 3 h; Concentrated sulfuric acid (mass fraction 98percent, 150mL) was added to the reactor to reduce the temperature.The temperature of the system is ≤ 10°C, the compound A liquid (3-chlorobenzaldehyde, 0.5 mol) is slowly added dropwise, and after addition, an appropriate amount of catalyst I2 (0.236-2.36 mmol, 30 mg in this example) is added.When 3-chlorobenzaldehyde and catalyst 12 were added, there was a clear exothermic phenomenon and the reaction temperature of the system was controlled to be ≤ 10°C; System temperature control ≤15°C, add in batches 5-10 timesNBS (N-bromosuccinimide, 0.5 mol); Insulation reaction for 2h, slowly rise to 25 °C, and stir the reaction for 1h,GC detection of raw materials 3_ chlorobenzaldehyde content ≤ 1 percent,The reaction solution was purified by post-treatment to obtain an acicular off-white solid compound (98 g, purity 98.0percent, yield 90.1 percent).
Reference: [1] Patent: CN107879918, 2018, A, . Location in patent: Paragraph 0034-0037; 0058-0065; 0070-0085
[2] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 888 - 896
[3] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6414 - 6420
  • 48
  • [ 108-41-8 ]
  • [ 587-04-2 ]
  • [ 216443-78-6 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 19, p. 8678 - 8688
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