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[ CAS No. 4180-23-8 ] {[proInfo.proName]}

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Chemical Structure| 4180-23-8
Chemical Structure| 4180-23-8
Structure of 4180-23-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4180-23-8 ]

CAS No. :4180-23-8 MDL No. :MFCD00009284
Formula : C10H12O Boiling Point : -
Linear Structure Formula :- InChI Key :RUVINXPYWBROJD-ONEGZZNKSA-N
M.W : 148.20 Pubchem ID :637563
Synonyms :
(E)​-Anethole;(E)-Anethol;NSC 209529;4-Propenylanisole

Calculated chemistry of [ 4180-23-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.83
TPSA : 9.23 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) : -4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.55
Log Po/w (XLOGP3) : 3.3
Log Po/w (WLOGP) : 2.62
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 2.79
Consensus Log Po/w : 2.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.115 mg/ml ; 0.000777 mol/l
Class : Soluble
Log S (Ali) : -3.17
Solubility : 0.1 mg/ml ; 0.000677 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.98
Solubility : 0.155 mg/ml ; 0.00104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 4180-23-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280 UN#:N/A
Hazard Statements:H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4180-23-8 ]

* 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 [ 4180-23-8 ]
  • Downstream synthetic route of [ 4180-23-8 ]

[ 4180-23-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 4180-23-8 ]
  • [ 18274-81-2 ]
YieldReaction ConditionsOperation in experiment
50% With sulfur In N,N-dimethyl-formamide for 8 h; Heating Anethole (1) (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2N-aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 300° C. This product was dissolved in boiling water and gave an orange precipitate (2) after addition of hydrochloric acid (Yield 50percent), m.p. 188-189° C. 1H NMR (DMSO) δ 6.86 (d, 2H), 7.68 (s, 1H), 7.75 (d, 2H), 10.51 (s, -OH); MS (ESI), m/z 225(M-).
50%
Stage #1: With sulfur In N,N-dimethyl-formamide for 8 h; Heating / reflux
Stage #2: With sodium hydroxide; water In toluene
Stage #3: at 100℃;
EXAMPLE 3General synthetic procedure of:4- or 5-Amino-2-hydroxy-benzoic acid 4-(5-thioxo-5H-[1,2]dithiol-3-yl)-phenyl ester(4)4- or 5-nmlno salicylic acidSynthesis of5-p-hydroxyphenyl-1,2-dithione-3-thione (ADT-OH)Anethole 1 (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2N- aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 3000C. This product was dissolved in boiling water and gave an orange precipitate 2 after addition of hydrochloric acid (Yield 50percent), m.p. 188-189 0C. 1H NMR (DMSO) δ6.86 (d, 2H), 7.68 (s, 1 H), 7.75 (d, 2H), 10.51 (s, -OH); MS (ESI), m/z 225{W).; EXAMPLE 6General synthetic procedure of:4-or 5-Amino-2-[4-(5-thioxo-5H-[1,2]dithiol-3-yl)-phenoxycarbonyloxy]-benzoic acid (15)2-Hydroxy-4-or 5-[4-(5-thioxo-5H-[1,2]dithiol-3-yl)-phenoxycarbonylamino]- benzoic acid (16) EPO <DP n="48"/> EPO <DP n="49"/>Synthesis of 5-p-hydroxyphenyl-t ,2-dithione-3-thione (ADT-OH)Anetholβ 1 (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2 N- aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 3000C. This product was dissolved in boiling water and gave an orange precipitate 2 after addition of hydrochloric acid (Yield 50percent), m.p. 188-189 0C. 1H NMR (DMSO) δ 6.86 (d, 2H), 7.68 (s, 1 H), 7.75 (d, 2H), 10.51 (s, -OH); MS (ESI), m/z225(M").
50%
Stage #1: With sulfur In N,N-dimethyl-formamide for 8 h; Heating / reflux
Stage #3: at 100℃;
EXAMPLE 3General synthetic procedure of:4- or 5-Amino-2-hydroxy-benzoic acid 4-(5-thioxo-5H-[1,2]dithiol-3-yl)-phenyl ester(4)4- or 5-nmlno salicylic acidSynthesis of5-p-hydroxyphenyl-1,2-dithione-3-thione (ADT-OH)Anethole 1 (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2N- aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 3000C. This product was dissolved in boiling water and gave an orange precipitate 2 after addition of hydrochloric acid (Yield 50percent), m.p. 188-189 0C. 1H NMR (DMSO) δ6.86 (d, 2H), 7.68 (s, 1 H), 7.75 (d, 2H), 10.51 (s, -OH); MS (ESI), m/z 225{W).; EXAMPLE 6General synthetic procedure of:4-or 5-Amino-2-[4-(5-thioxo-5H-[1,2]dithiol-3-yl)-phenoxycarbonyloxy]-benzoic acid (15)2-Hydroxy-4-or 5-[4-(5-thioxo-5H-[1,2]dithiol-3-yl)-phenoxycarbonylamino]- benzoic acid (16) EPO <DP n="48"/> EPO <DP n="49"/>Synthesis of 5-p-hydroxyphenyl-t ,2-dithione-3-thione (ADT-OH)Anetholβ 1 (32.5 g; 0.21 mol) and sulphur (45 g; 1.40 mol) were heated in dimethylformamide (250 ml) for 8 hr; the residue after removal of solvent was almost completely soluble in toluene. An attempt to extract the toluene liquors with 2 N- aqueous sodium hydroxide, gave a precipitate of an orange solid (8.5 g). m.p. over 3000C. This product was dissolved in boiling water and gave an orange precipitate 2 after addition of hydrochloric acid (Yield 50percent), m.p. 188-189 0C. 1H NMR (DMSO) δ 6.86 (d, 2H), 7.68 (s, 1 H), 7.75 (d, 2H), 10.51 (s, -OH); MS (ESI), m/z225(M").
13%
Stage #1: With sulfur In N,N-dimethyl-formamide for 8 h; Heating / reflux
Stage #2: With sodium hydroxide In water; toluene
Stage #3: With hydrogenchloride In waterHeating / reflux
Synthesis of 5-p-hydroxyphenyl-1,2-dithiole-3-thione (2; ADT-OH)
Anethole (31 g, 0.21 mol) and sulfur (44.8 g, 1.40 mol) were heated in N,N-dimethylformamide (250 ml) for 8 hrs; after removal of solvent, the residue was almost completely soluble in toluene.
An attempt to extract the toluene liquors with 2N-aqueous sodium hydroxide, gave an orange solid precipitate (8.5 g; m.p. over 300° C.).
This product was dissolved in boiling water and, after addition of hydrochloric acid, gave 2 as an orange precipitate (6.2 g, yield 13percent) m.p. 188-189° C.
1H NMR (DMSO-d6) δ 6.86 (d, 2H), 7.68 (s, 1H), 7.75 (d, 2H), 10.51 (s, -OH); MS (ESI), m/z 225 (M-).

Reference: [1] Patent: US2006/270635, 2006, A1, . Location in patent: Page/Page column 12; 16-17
[2] Patent: WO2006/125293, 2006, A1, . Location in patent: Page/Page column 36-37; 47
[3] Patent: WO2006/125295, 2006, A1, . Location in patent: Page/Page column 40-41; 51
[4] Patent: US2008/4245, 2008, A1, . Location in patent: Page/Page column 10
  • 2
  • [ 4180-23-8 ]
  • [ 532-11-6 ]
YieldReaction ConditionsOperation in experiment
32% With sulfur In neat (no solvent) at 200℃; for 0.166667 h; Microwave irradiation Entry 10: Anethole (500 mg, 1.0 eq.) and elemental sulfur (433 mg, 4.0 eq.) were added with a magnetic stir bar to a 10 mL microwave reaction vessel and a condenser was attached. The reaction conditions were regulated through the CEM-software as follows: temperature: 200°C, power: 200 Watt, ramp time: 1 min, hold time: 9 min. After reaction completion, the vessel was removed from the reactor and cooled immediately in an ice bath and the 1H ΝΜR spectrum of the crude soluble reaction mixture was recorded. The crude material was purified by flash column chromatography (Hex/EtOAc 95:5) to afford 1 (256 mg, 32percent) as a dark red solid.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 24, p. 2378 - 2380
[2] Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 89,105
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1947, vol. 224, p. 479
[4] Patent: WO2006/66894, 2006, A1, . Location in patent: Page/Page column 16-19
[5] Patent: WO2006/134489, 2006, A1, . Location in patent: Page/Page column 13-14
[6] Patent: WO2006/111791, 2006, A1, . Location in patent: Page/Page column 8-10
[7] Patent: EP1939186, 2008, A1, . Location in patent: Page/Page column 6
[8] Patent: WO2008/146105, 2008, A1, . Location in patent: Page/Page column 17-18
  • 3
  • [ 4180-23-8 ]
  • [ 532-11-6 ]
  • [ 77150-78-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 89,105
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1947, vol. 224, p. 479
[3] Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 89,105
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1947, vol. 224, p. 479
  • 4
  • [ 4180-23-8 ]
  • [ 10557-27-4 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 11840 - 11843
[2] Farmaco (1946-1952), 1948, vol. 3, p. 125,133
[3] Bulletin of the Chemical Society of Japan, 1974, vol. 47, p. 2255 - 2259
  • 5
  • [ 4180-23-8 ]
  • [ 84-16-2 ]
Reference: [1] Journal of Organic Chemistry, 1949, vol. 14, p. 45,57
  • 6
  • [ 4180-23-8 ]
  • [ 14367-46-5 ]
Reference: [1] Farmaco (1946-1952), 1948, vol. 3, p. 125,133
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