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[ CAS No. 18362-30-6 ] {[proInfo.proName]}

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Chemical Structure| 18362-30-6
Chemical Structure| 18362-30-6
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Product Citations

Product Citations

Raaginie Tamil Segaran ; Chean Hui Ng ; Mohd Fadhlizil Fasihi Mohd Aluwi , et al. DOI:

Abstract: The synthesis of prenylated or geranylated acylphloroglucinol-based xanthenones with 15.1-36.9% yield was achieved via aldol condensation of 2,4,6-trihydroxy-3-prenylacetophenone (tHPA) or 2,4,6-trihydroxy-3-geranylacetophenone (tHGA) and 2-hydroxybenzaldehyde derivatives in the presence of lithium bis(trimethylsilyl)amide (LiHMDS) as deprotonating agent. This study is one of the first to report on the synthesis of xanthenones using strong non-nucleophilic base catalyst, and the described synthesis not only achieved a compound with a natural product skeleton but also formed in a simple and environmentally friendly specificity.

Keywords: Acylphloroglucinol-based xanthenone ; LiHMDS base catalyst ; Aldol condensation ; Natural product skeleton ; Eco-friendly

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Product Details of [ 18362-30-6 ]

CAS No. :18362-30-6 MDL No. :MFCD01646166
Formula : C7H5ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MVTWVXYIKIVAOJ-UHFFFAOYSA-N
M.W : 156.57 Pubchem ID :528393
Synonyms :

Calculated chemistry of [ 18362-30-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.86
TPSA : 37.3 ?2

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) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 2.14
Consensus Log Po/w : 1.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.58
Solubility : 0.411 mg/ml ; 0.00262 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.369 mg/ml ; 0.00236 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.663 mg/ml ; 0.00424 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.1

Safety of [ 18362-30-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18362-30-6 ]

* 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.

  • Downstream synthetic route of [ 18362-30-6 ]

[ 18362-30-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 56-18-8 ]
  • [ 18362-30-6 ]
  • bis-[3-(6-chloro-2-hydroxy-benzylidenamino)-propyl]-amine; cobalt (II)-salt [ No CAS ]
  • 2
  • [ 18362-30-6 ]
  • [ 108-24-7 ]
  • 1-acetoxy-3-chloro-2-diacetoxymethyl-benzene [ No CAS ]
  • 3
  • [ 18362-30-6 ]
  • [ 107-15-3 ]
  • <i>N</i>,<i>N</i>'-bis-(2-chloro-6-hydroxy-benzyliden)-ethylenediamine [ No CAS ]
  • 5
  • [ 4071-85-6 ]
  • [ 18362-30-6 ]
  • [ 38169-98-1 ]
  • 7
  • [ 387-45-1 ]
  • [ 18362-30-6 ]
YieldReaction ConditionsOperation in experiment
62% Potassium hydroxide (10 g) was added slowly to a stirred solution of 2-chloro-6-fluoro- benzaldehyde (14.0 g, 88.3 mmol) in dimethylsulfoxide (20 mL) at 0°C, the reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was diluted with water (100 mL) and acidified to pH 2 with concentrated HCl. The precipitates were filtered, washed with water (2x100 mL) and dried over anhydrous sodium sulfate, to give a residue which was used directly in the next step. Yield: 8.5 g (62percent). H NMR (400 MHz, CDCI3) delta ppm 6.85 - 7.02 (m, 2H) 7.39 - 7.47 (m, 1H) 10.41 (s, 1H) 11.95 (s, 1H).
61% 2-chloro-6-hydroxybenzaldehyde To a solution of 2-chloro-6-fluorobenzaldehyde (2.44 g, 15.4 mmol) in DMSO (20 mL) at 0° C. was added potassium hydroxide (2.23 g, 33.8 mmol) slowly. The reaction mixture was allowed to stir and warm to rt overnight and then diluted with water (65 mL). The mixture was acidified to pH<1 with conc. HCl. A white solid formed and was filtered, washed with water, and dried to give 2-chloro-6-hydroxybenzaldehyde (1.48 g, 61percent). LCMS: (FA) ES-155.0.
With potassium hydroxide; In water; dimethyl sulfoxide; Step D Synthesis of 6-chlorosalicylaldehyde as an intermediate A stirred solution of 40.0 grams (0.252 mole) of 2-chloro-6-fluorobenzaladehyde in 300 mL of dimethylsulfoxide was cooled to 15° C., and 36.6 grams (0.555 mole) of powdered 85percent potassium hydroxide was added portionwise at a rate to maintain the reaction mixture temperature below 25° C. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 18 hours. After this time the reaction mixture was poured into 1000 mL of water and was acidified with concentrated hydrochloric acid, with stirring. The resultant solid was collected by filtration, washed with water, and dried to yield 30.1 grams of 6-chlorosalicylaldehyde; m.p. 50°-52° C.
  • 8
  • [ 18362-30-6 ]
  • [ 108-24-7 ]
  • [ 38169-98-1 ]
  • 9
  • [ 18362-30-6 ]
  • [ 685-87-0 ]
  • ethyl 4-chlorobenzofuran-2-carboxylate [ No CAS ]
  • 10
  • [ 18362-30-6 ]
  • [ 75-36-5 ]
  • [ 151222-25-2 ]
  • 11
  • [ 18362-30-6 ]
  • [ 572-09-8 ]
  • [ 159194-03-3 ]
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Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Kinetics of Alkyl Halides ? Knoevenagel Condensation ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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