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[ CAS No. 50889-29-7 ] {[proInfo.proName]}

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Chemical Structure| 50889-29-7
Chemical Structure| 50889-29-7
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Product Details of [ 50889-29-7 ]

CAS No. :50889-29-7 MDL No. :MFCD00055556
Formula : C24H26BrO2P Boiling Point : -
Linear Structure Formula :- InChI Key :JUWYRPZTZSWLCY-UHFFFAOYSA-N
M.W : 457.34 Pubchem ID :2779280
Synonyms :

Calculated chemistry of [ 50889-29-7 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.21
Num. rotatable bonds : 9
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 125.75
TPSA : 50.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : -1.16
Log Po/w (XLOGP3) : 6.16
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 5.54
Log Po/w (SILICOS-IT) : 5.56
Consensus Log Po/w : 3.55

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -6.44
Solubility : 0.000167 mg/ml ; 0.000000365 mol/l
Class : Poorly soluble
Log S (Ali) : -7.01
Solubility : 0.0000445 mg/ml ; 0.0000000972 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.88
Solubility : 0.000000599 mg/ml ; 0.0000000013 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.58

Safety of [ 50889-29-7 ]

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 [ 50889-29-7 ]

* 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 [ 50889-29-7 ]
  • Downstream synthetic route of [ 50889-29-7 ]

[ 50889-29-7 ] Synthesis Path-Upstream   1~12

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Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 12, p. 1239 - 1241
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  • [ 25775-90-0 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, p. 3477 - 3478
  • 3
  • [ 4224-70-8 ]
  • [ 603-35-0 ]
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YieldReaction ConditionsOperation in experiment
98% for 48 h; Heating / reflux A solution of6-bromohexanoic acid (10.00 g, 51.27 mmol) and triphenyl phosphine (14.12 g, 53.83 mmol) in freshly distilled acetonitrile (50 mL) was vigorously stirred and refluxed for 48 hours. The solution was allowed to come to ambient temperature and the Wittig salt was precipitated upon scratching the inside wall of the glass reaction vessel with a spatula. The white solid product was collected, washed with ether and filtered to provide the title compound in 98percent yield (22.87 g): 1H NMR (400 MHz1 CD3OD) δ 1.62-1.72 (m, 6H), 2.29 (t, 2H), 3.40-3.47 (m, 2H), 7.76-7.91 (m, 15H)
97.5% for 72 h; Reflux Triphenylphosphine (20 mg, 0.076 mmol) and 6-bromohexanoic acid (14.8 mg, 0.076 mmol) were dissolved in dry toluene (0.2 mL). The reaction mixture was refluxed over 72 hours. The solution was concentrated. The residue was washed consecutively with benzene (3 x 1 mL), hexane (1 mL), and Et20 (2 x 1 mL). The crystalline white solid was dried to give the pure product (28 mg, 97.5 percent). 1H NMR (300 MHz, CDC13) δ 7.80-7.68 (m, 15H), 3.58 (bs, 2H), 2.34-2.32 (m,2H), 1.63-1.57 (m, 6H). EI-MS (m z): Calcd for C24H2602P+ 377.16; found 377.1
95% for 20 h; Heating / reflux A solution of 6-bromohexanoic acid (3.9 g, 20.0 mmol, 1 equiv) in anhydrous acetonitrile (16 mL) was treated with triphenylphosphine (6.3 g, 24.0 mmol, 1.2 equiv) and warmed at reflux for 20 h. The reaction mixture was concentrated and the crude product was purified by column chromatography (SiO2, 5.5 x 8 cm, 50-100percent EtOAc-hexanes gradient and then 5percent MeOH-CH2Cl2) to afford Sl (8.7 g, 19.0 mmol, 95percent) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 7.78-7.67 (m, 15H), 3.58 (m, 2H), 2.33 (m, 2H), 1.63 (m, 4H).
94% for 48 h; Inert atmosphere; Reflux General procedure: A mixture of ω-bromocarboxylic acid (1 equiv) and triphenylphosphine (1 equiv) in 300 mL of toluene was refluxed for 48 h under argon. The mixture was allowed to cool at room temperature and concentrated in vacuum. The residue was crystallized from various solvents to give the corresponding phosphonium salt.
91% for 24 h; Reflux Example 1
Synthesis of TPP-(CH2)5-COOH
A mixture of 6-bromohexanoic acid (2.0 g, 10.3 mmol) and TPP (2.8 g, 10.8 mmol) was heated to reflux for 24 h in acetonitrile.
The solvent was evaporated to dryness.
The resulting residue was washed with hexane-diethyl ether (3*30 mL) followed by vacuum drying to afford a white solid as a pure product. Yield: 91percent (4 g).
Melting point: 200-205° C.; 1H NMR (CDCl3): δ 9.3 (s, 1H), 7.6-7.8 (m, 15H), 3.5 (t, 2H), 2.3 (t, 2H), 1.6 (m, 6H).
13C NMR (CDCl3): δ 175, 135, 133.6, 130.6, 118.5, 34.2, 29.37, 23.9, 22.8, 22.29, 21.9. 31P NMR (CDCl3) 24.34. ppm. HRMS-ESI (m/z): [M-Br]+ calcd. for C24H26O2P+, 377.1665. found, 377.1629.
65% for 24 h; Inert atmosphere; Reflux Bromohexanoic acid (0.600 g, 3.076 mmol) and triphenylphosphine (0.968 g 3.691 mmol) were dissolved in 40 mL of acetonitrile.This reaction was refluxed for 24 h under a N2 environment. After 24 h, the solvent was evaporated to yield an oil, which was then precipitated with diethyl ether. The precipitate was filtered through a glass frit filter, and washed several times with diethyl ether to remove any impurities from the starting materials. The product was kept on vacuum for 1 h. Yield 0.760 g 65percent. 1H NMR (CDCl3, 400 MHz): δ 7.78 [m, 15H], 3.56 [m, 2H], 2.44 [m, 2H], 1.68 [m, 6H] ppm.
55% for 20 - 24 h; Heating / reflux A solution of 6-Bromohexanoic acid (3g, 0.0512 moles) and triphenylphosphine 4.8g, 0.018 moles) in dry acetonitrile (5OmL) was refluxed for 20-24 h and excess solvent was removed under reduced pressure to afford a color less oil which was triturated with dry benzene and wash in succession with dry benzene and ether (3 times each). During the washing procedure the material crystallized drying at reduced pressure afford Wittig salt as a white micro- crystalline powder (3.6g, 55percent yield).
55% Reflux A solution of 6-Bromohexanoic acid (3 g, 0.0512 moles) and triphenylphosphine 4.8 g, 0.018 moles) in dry acetonitrile (50 mL) was refluxed for 20-24 h and excess solvent was removed under reduced pressure to afford a color less oil which was triturated with dry benzene and wash in succession with dry benzene and ether (3 times each). During the washing procedure the material crystallized drying at reduced pressure afford Wittig salt as a white micro-crystalline powder (3.6 g, 55percent yield).

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  • [ 502-44-3 ]
  • [ 6399-81-1 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 4, p. 685 - 696
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Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2240 - 2243
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Reference: [1] Tetrahedron Asymmetry, 2003, vol. 14, # 13, p. 1799 - 1806
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Reference: [1] Tetrahedron Asymmetry, 2003, vol. 14, # 13, p. 1799 - 1806
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Reference: [1] Patent: CN106632474, 2017, A,
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Reference: [1] Patent: CN106632474, 2017, A,
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