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[ CAS No. 645-45-4 ] {[proInfo.proName]}

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Chemical Structure| 645-45-4
Chemical Structure| 645-45-4
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Product Details of [ 645-45-4 ]

CAS No. :645-45-4 MDL No. :MFCD00000748
Formula : C9H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :MFEILWXBDBCWKF-UHFFFAOYSA-N
M.W : 168.62 Pubchem ID :64801
Synonyms :

Calculated chemistry of [ 645-45-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.02
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) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 2.82
Log Po/w (WLOGP) : 2.38
Log Po/w (MLOGP) : 2.4
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 2.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.229 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (Ali) : -2.84
Solubility : 0.246 mg/ml ; 0.00146 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.76
Solubility : 0.029 mg/ml ; 0.000172 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 645-45-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P261-P264-P270-P271-P280-P301+P312-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P321-P322-P330-P363-P405-P501 UN#:3265
Hazard Statements:H302-H312-H314-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 645-45-4 ]

* 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 [ 645-45-4 ]
  • Downstream synthetic route of [ 645-45-4 ]

[ 645-45-4 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 501-52-0 ]
  • [ 645-45-4 ]
YieldReaction ConditionsOperation in experiment
100% With oxalyl dichloride In dichloromethane at 20℃; 3-Phenylpropanoyl chloride (74). A 200 mL flask fitted with a stir-bar and septum with an Ar inlet was charged with hydrocinnamic acid (5.00 g, 33.3 mmol), DMF (0.1 mL), and CH2CI2 (30 mL). To the resultant solution was added (COCI)2 (2M in CH2CI2, 20.0 mL, 40.0 mmol) over 30 min. The mixture stirred overnight at rt, and then was concentrated in vacuo to give 5.9 g of 74 as a yellow oil (100percent). HPLC analysis (15:10:75 H2O:A1 :MeOH) showed a purity of 99percent with a retention time of 5.3 min.
100% With oxalyl dichloride In dichloromethane for 24 h; Inert atmosphere To a stirred solution of 3-phenylpropanoic acid (3.0 g, 20 mmol, 1 eq.) in anhydrous CH2Cl2 (165 mL) under nitrogen was added oxalyl chloride (16.5 mL 190 mmol, 10 eq.) rapidly via syringe. The reaction mixture was stirred for 24 h, after which the solvent and unreacted oxalyl chloride were Removed by distillation under reduced pressure. The resulting yellow liquid was concentrated via azeotrope with benzene (3 x 50 mL) in vacuo and dried under a vacuum to yield 37 (3.4 g, ~100percent) as a yellow liquid, which was used directly in the next step.
95% With thionyl chloride In benzene for 4 h; Reflux Dihydrocinnamic acid (10b) (3.0g, 0.02mol) was dissolved in dry benzene (5mL, 0.06mol) at room temperature then SOCl2 (10mL, 0.14mol) was added in a dropwise manner. The reaction mixture was allowed to heat at reflux for 4h. The solvent was evaporated under reduced pressure to give (3.4g, 95percent) of 11b as yellow oil. The crude product was used in the next step without further purification or characterization.
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  • 2
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  • 3
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  • 5
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  • 6
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  • 7
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  • 8
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  • 9
  • [ 119541-41-2 ]
  • [ 645-45-4 ]
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  • [ 645-45-4 ]
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  • 13
  • [ 645-45-4 ]
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  • 14
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  • [ 29898-25-7 ]
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  • 16
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  • 18
  • [ 645-45-4 ]
  • [ 18107-18-1 ]
  • [ 31984-10-8 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: at 0℃; for 3.1 h;
Stage #2: With hydrogen bromide In water; acetic acid at 0℃; for 0.166667 h;
(i) A soln of 3-phenyl-propionyl chloride (2.0 mL; 13.5 mmol) in dry THF (50 mL) was added over 6 min to a 0 °C soln of diazomethyl-trimethyl-silane (2.0 M in hexanes; 15 mL; 30 mmol) in dry THF (50 mL). After 3 h, the rxn was coned to a liquid, (ii) Aq. HBr (48percent; ca. 2.5 eq) was added in one portion to a soln of this crude material in AcOH (30 mL) at 0 °C. After 10 min the rxn was coned. EtOAc (50 mL) was added and the soln washed with water (2 x 15 mL), satd NaHCO3 (3 x 15 mL), water (1 x 15 mL) and satd NaCl (2 x 15 mL). After drying over MgSO4, filtering through a pad of silica with an EtOAc wash and coned to an oil, the crude material was purified by MPLC (SiO2 with a 0 - > 20percent EtOAc in hexanes gradient) yielding bromomethyl ketone as an off-white solid (1.977 g; 65percent). IH NMR (CDC13) δ 7.37 - 7.18 (m, 5H), 3.85 (s, 2H), 3.01 - 2.94 (m, 4H); GC-MS 226/228 ([M]+).
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  • 20
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  • 21
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  • [ 645-45-4 ]
  • [ 51135-91-2 ]
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  • 23
  • [ 645-45-4 ]
  • [ 69975-65-1 ]
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  • [ 316146-27-7 ]
YieldReaction ConditionsOperation in experiment
92% at 0 - 20℃; Inert atmosphere To a solution of 4-bromobenzenmine (40g, 0.232mol) and Et3N (32mL) in CH2Cl2 (200mL), benzenepropanoylchoride (37.5g, 0.223mol) was added dropwise at 0°C, and the mixture was stirred overnight at room temperature. Then, the mixture was poured out into water and 10percent HCl was added. The slurry of white solid which formed was stirred with ice-bath cooling for 1 hour. The solid was separated by filtration, washed with diethyl ether and air dried to give 62g (92percent yield) of compound 1.
87% With triethylamine In dichloromethane at 20℃; Benzenepropanoyl chloride (0.488 mol) was added dropwise at room temperature to a solution of 4-bromo benzenamine (0.407 mol) in Et3N (70ml) and DCM (700ml) and the mixture was stirred at room temperature overnight The mixture was poured out into water and concentrated NH40H, and extracted with DCM. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was crystallized from diethyl ether. The residue (119. 67g) was taken up in DCM and washed with HCI IN. The organic layer was dried (MgS04), filtered, and the solvent was evaporated, yielding 107.67g of intermediate 1 (87percent).
87% With triethylamine In dichloromethane at 20℃; Example A2; a) Preparation of intermediate 4; Benzene propanoyl chloride (0.488 mol) was added dropwise at room temperature to a solution of 4-bromobenzenamine (0.407 mol) in Et3N (70 ml) and CH2Cl2 (700 ml) and the mixture was stirred at room temperature overnight. The mixture was poured out into water and concentrated NH4OH, and extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was crystallized from diethyl ether. The residue (119.67 g) was taken up in CH2Cl2 and washed with HCl IN. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. Yield: 107.67 g of intermediate 4 (87 percent).
87% With triethylamine In dichloromethane at 20℃; Example A1: Preparation of intermediate 1. Benzenepropanoyl chloride (0.488 mol) was added dropwise at room temperature to a solution of 4-bromo benzenamine (0.407 mol) in Et3N (70ml) and DCM (700ml) and the mixture was stirred at room temperature overnight. The mixture was poured out into water and concentrated NH4OH, and extracted with DCM. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was crystallized from diethyl ether. The residue (119.67g) was taken up in DCM and washed with HCl 1N. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated, yielding 107.67g of intermediate 1 (87percent).
81% With triethylamine In dichloromethane at 0 - 20℃; for 4 h; Preparation ofN-(4-Bromo phenyl )-3-phenyl propionamide; Hydrocmnamoyl chloride (19.6 g, 168.5 mmol) was added to a mixture of 4-bromoanline (10.0 g, 116.3 mmol) and triethylamine (23 5 g, 232.5 mmol) in dry dichloromethane (200 ml) at 0 0C, the mixture was stirred, and allowing it to warm up to room temperature during 4 brs The reaction mixture was poured mto ice-water mixture, the organic layer was separated, washed with 10percent aqueous solution of hydrochloric acid, water and brme, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product, which was triturated with hexane to furnish the pure product (11.0 g, 81percent) as a off white solid, Mp 149-151°C. 1H NMR (400 MHz, CDCl3) δ 2.64 (t, J = 8.0 Hz, 2 H), 3.04 (t, J = 8 0 Hz, 2 H), 7.01 (br s, 1 H, D2O exchangeable), 6.88-7.30 (m, 3 H), 7.26-7.33 (m, 4 H), 7.36-7.43 (m, 2 H). (M+H)+= 302, 304.

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[11] Patent: WO2007/435, 2007, A1, . Location in patent: Page/Page column 43-44
[12] Patent: WO2007/436, 2007, A1, . Location in patent: Page/Page column 33
[13] Patent: WO2007/14934, 2007, A2, . Location in patent: Page/Page column 32-33
  • 26
  • [ 645-45-4 ]
  • [ 654655-68-2 ]
Reference: [1] ChemMedChem, 2017, vol. 12, # 2, p. 106 - 119
  • 27
  • [ 645-45-4 ]
  • [ 654655-69-3 ]
Reference: [1] ChemMedChem, 2017, vol. 12, # 2, p. 106 - 119
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