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[ CAS No. 23377-40-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 23377-40-4
Chemical Structure| 23377-40-4
Chemical Structure| 23377-40-4
Structure of 23377-40-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 23377-40-4 ]

CAS No. :23377-40-4 MDL No. :MFCD00171483
Formula : C19H40O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YDCSFYSJEYSCBP-UHFFFAOYSA-N
M.W : 300.52 Pubchem ID :165753
Synonyms :

Calculated chemistry of [ 23377-40-4 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 18
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 95.69
TPSA : 29.46 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) : -2.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.97
Log Po/w (XLOGP3) : 7.5
Log Po/w (WLOGP) : 5.87
Log Po/w (MLOGP) : 4.24
Log Po/w (SILICOS-IT) : 6.56
Consensus Log Po/w : 5.83

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.24
Solubility : 0.00173 mg/ml ; 0.00000575 mol/l
Class : Moderately soluble
Log S (Ali) : -7.95
Solubility : 0.00000335 mg/ml ; 0.0000000112 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.71
Solubility : 0.0000589 mg/ml ; 0.000000196 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.47

Safety of [ 23377-40-4 ]

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 [ 23377-40-4 ]

* 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 [ 23377-40-4 ]
  • Downstream synthetic route of [ 23377-40-4 ]

[ 23377-40-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 112-82-3 ]
  • [ 504-63-2 ]
  • [ 23377-40-4 ]
YieldReaction ConditionsOperation in experiment
88.4% With potassium hydroxide In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 16 h; In a 1000ml round bottom flask,Add n-hexadecyl bromide (2) 97.5 g (0.32 mol, 1 eq), 1,3-propanediol (3) 73.5 g (0.96 mol, 3 eq),DMSO 200ml,DMF 200ml andPotassium hydroxide 72g (1.28mol, 4eq), stirred at room temperature16h.After completion of the reaction, 500 ml of water was added to the reaction solution, then the pH was adjusted to neutrality with a 5M hydrochloric acid solution, and the mixture was extracted with ethyl acetate (500 ml×2). The organic layers were combined and the organic layer was washed with saturated brine (500 ml×2). ), collecting organic phase,Dry with 10 g of anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain 102 g of a yellow solid.Recrystallization of petroleum ether yielded 85 g of white flake-like crystals with a yield of 88.4percent.
77%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; oil at 0 - 20℃; for 0.166667 h;
Stage #2: With potassium iodide In N,N-dimethyl-formamide; oil at 95℃; for 4 h;
General procedure: To a solution of 1,3-propanediol (19) (6.51 mL, 90 mmol) in dry DMF (40 mL) was added NaH (60percent oil dispersion; 1.20 g, 30 mmol) in installments at 0 °C and the mixture was stirred at room temperature for 10 min. Dodecyl bromide (4.80 mL, 20 mmol) and KI (3.32 g, 20 mmol) were added and the mixture was heated at 95 °C for 4 h. After cooling, the mixture was poured into ice-water and extracted with AcOEt. The extracts were washed with brine, dried over Na2SO4 and evaporated. The resulting residue was purified by flash CC (silica gel; AcOEt/hexane, 1:2) to provide dodecyl ether 20a (3.38 g, 69percent). Tetradecyl ether 20b (79percent) and hexadecyl ether 20c (77percent) were similarly prepared from 1,3-propanediol (19).
Reference: [1] Patent: CN107936059, 2018, A, . Location in patent: Paragraph 0011; 0029; 0030
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3658 - 3665
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2002, vol. 177, # 12, p. 2887 - 2893
[4] Chemistry and Physics of Lipids, 1996, vol. 83, # 1, p. 77 - 85
[5] Molecular Therapy - Nucleic Acids, 2017, vol. 8, p. 158 - 168
  • 2
  • [ 6068-28-6 ]
  • [ 504-63-2 ]
  • [ 23377-40-4 ]
Reference: [1] ChemMedChem, 2013, vol. 8, # 3, p. 511 - 520
  • 3
  • [ 20779-14-0 ]
  • [ 504-63-2 ]
  • [ 23377-40-4 ]
Reference: [1] Patent: US2012/58976, 2012, A1, . Location in patent: Page/Page column 18
  • 4
  • [ 36653-82-4 ]
  • [ 23377-40-4 ]
Reference: [1] Patent: US2012/58976, 2012, A1,
[2] ChemMedChem, 2013, vol. 8, # 3, p. 511 - 520
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