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[ CAS No. 4009-98-7 ] {[proInfo.proName]}

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Chemical Structure| 4009-98-7
Chemical Structure| 4009-98-7
Structure of 4009-98-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4009-98-7 ]

CAS No. :4009-98-7 MDL No. :MFCD00011800
Formula : C20H20ClOP Boiling Point : -
Linear Structure Formula :- InChI Key :SJFNDMHZXCUXSA-UHFFFAOYSA-M
M.W : 342.80 Pubchem ID :2723798
Synonyms :

Calculated chemistry of [ 4009-98-7 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.1
Num. rotatable bonds : 5
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 102.76
TPSA : 22.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : -1.17
Log Po/w (XLOGP3) : 5.37
Log Po/w (WLOGP) : 0.59
Log Po/w (MLOGP) : 4.78
Log Po/w (SILICOS-IT) : 4.62
Consensus Log Po/w : 2.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.6
Solubility : 0.000866 mg/ml ; 0.00000253 mol/l
Class : Moderately soluble
Log S (Ali) : -5.6
Solubility : 0.000855 mg/ml ; 0.0000025 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.06
Solubility : 0.00000297 mg/ml ; 0.0000000086 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.48

Safety of [ 4009-98-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P337+P313-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4009-98-7 ]

* 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 [ 4009-98-7 ]
  • Downstream synthetic route of [ 4009-98-7 ]

[ 4009-98-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 107-30-2 ]
  • [ 603-35-0 ]
  • [ 4009-98-7 ]
YieldReaction ConditionsOperation in experiment
97.3% at 95℃; for 16 h; 20 g of triphenylphosphine was placed in a round bottom flask, dissolved in toluene, heated to 95 ° C, and 6.37 mL of chloromethyl methyl ether was added, and the reaction was carried out for 16 hours. After the reaction is complete,Cool to room temperature, filter, filter cake washed with toluene three times, dry,Obtained 25.4 g of white phosphonium salt, yield 97.3percent
88.5% at 37 - 47℃; for 6 h; Inert atmosphere Under nitrogen, 50 mL of anhydrous acetone was added to the reactor,Then 32 g of triphenylphosphine was added,While stirring, the temperature was raised to 37 ° C,While maintaining the temperature, 20 g of methyl chloromethyl ether was added to the reactor,Followed by reaction at 37 ° C for 3 h,The temperature was gradually raised to 47 ° C at a rate of 1 ° C / min and the reaction was continued for 3 h,The reaction was stopped, filtered, washed with anhydrous ether, dried,To give 37.0 g (methoxymethyl) triphenylphosphonium chloride in a yield of 88.5percent.
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 5, p. 596 - 600
[2] Patent: CN107936009, 2018, A, . Location in patent: Paragraph 0042; 0087-0088
[3] Bulletin of the Chemical Society of Japan, 1980, vol. 53, # 12, p. 3436 - 3438
[4] Patent: CN106588982, 2017, A, . Location in patent: Paragraph 0008; 0017; 0018; 0019; 0020; 0021; 0022-0025
[5] Journal of the American Chemical Society, 1976, vol. 98, p. 6613 - 6623
[6] Journal of the American Chemical Society, 1978, vol. 100, p. 7304 - 7311
[7] Chemische Berichte, 1961, vol. 94, p. 1373 - 1383
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1979, p. 3099 - 3106
[9] Journal of the American Chemical Society, 1958, vol. 80, p. 6150
[10] Tetrahedron, 1964, vol. 20, p. 449 - 459
[11] Tetrahedron, 1999, vol. 55, # 3, p. 625 - 636
[12] Journal of Fluorine Chemistry, 2012, vol. 139, p. 4 - 11
  • 2
  • [ 19125-34-9 ]
  • [ 4009-98-7 ]
  • [ 111153-74-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 7, p. 2825 - 2839
  • 3
  • [ 4009-98-7 ]
  • [ 127406-08-0 ]
YieldReaction ConditionsOperation in experiment
71% With sodium hexamethyldisilazane In tetrahydrofuran Step A
2-[4-[(E)-2-methoxyethenyl]phenyl]-pyrazine
Sodium hexamethyldisilazide (10.80 mL, 10.80 mmol, 11.0M in THF) was added to a suspension of methoxymethyltriphenylphosphonium chloride (3.72 g, 10.80 mmol) in THF (20 mL) at -10° C., and the red-orange mixture was stirred for 15 min at -10° C. A solution of 4-pyrazinylbenzaldehyde (1.00 g, 5.43 mmol) prepared as described in reference example 17) in THF (3 mL) was added dropwise, and stirring was continued at -10° C. for 1 h.
The reaction mixture was quenched with sat.
aq. NH4Cl, extracted with ethyl acetate, the organic layer dried with Na2SO4, and concentrated in vacuo.
Purification by medium pressure liquid chromatography (SiO2, 3:1 hexane/ethyl acetate) yielded 820 mg (71percent) of the title compound (E:Z=1:1). MS 213 (M+H)+.
Reference: [1] Patent: US2003/220272, 2003, A1,
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