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[ CAS No. 27374-25-0 ] {[proInfo.proName]}

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Excepted Quantity USD 0.00
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Chemical Structure| 27374-25-0
Chemical Structure| 27374-25-0
Structure of 27374-25-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 27374-25-0 ]

CAS No. :27374-25-0 MDL No. :MFCD00074986
Formula : C8H18O2Si Boiling Point : -
Linear Structure Formula :- InChI Key :BZMMRNKDONDVIB-UHFFFAOYSA-N
M.W : 174.31 Pubchem ID :2734686
Synonyms :

Calculated chemistry of [ 27374-25-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.53
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.96
Log Po/w (XLOGP3) : 2.19
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 1.31
Log Po/w (SILICOS-IT) : 0.6
Consensus Log Po/w : 1.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.04
Solubility : 1.6 mg/ml ; 0.0092 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.07 mg/ml ; 0.00615 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.23
Solubility : 1.02 mg/ml ; 0.00583 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.79

Safety of [ 27374-25-0 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P302+P352-P305+P351+P338 UN#:1993
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 27374-25-0 ]

* 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 [ 27374-25-0 ]
  • Downstream synthetic route of [ 27374-25-0 ]

[ 27374-25-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 201230-82-2 ]
  • [ 27374-25-0 ]
  • [ 6317-49-3 ]
Reference: [1] Tetrahedron, 1991, vol. 47, # 24, p. 3935 - 3946
[2] Tetrahedron Letters, 1988, vol. 29, # 13, p. 1541 - 1542
  • 2
  • [ 27374-25-0 ]
  • [ 539-74-2 ]
Reference: [1] Journal of the American Chemical Society, 1983, vol. 105, p. 651
  • 3
  • [ 75-77-4 ]
  • [ 623-71-2 ]
  • [ 27374-25-0 ]
Reference: [1] Organic Letters, 2000, vol. 2, # 11, p. 1609 - 1611
[2] Organic Syntheses, 1985, vol. 63, p. 147 - 147
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 35, p. 9266 - 9270[4] Angew. Chem., 2013, vol. 125, # 35, p. 9436 - 9440
[5] Organic Letters, 2013, vol. 15, # 22, p. 5890 - 5893
[6] Chemistry - A European Journal, 2015, vol. 21, # 14, p. 5561 - 5583
[7] Journal of the American Chemical Society, 1987, vol. 109, # 16, p. 4954 - 4960
[8] Synthesis, 1971, p. 236 - 253
[9] Journal of the American Chemical Society, 1986, vol. 108, p. 3745
  • 4
  • [ 7677-24-9 ]
  • [ 74592-24-8 ]
  • [ 27374-25-0 ]
  • [ 13837-45-1 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 21, p. 4129 - 4135
  • 5
  • [ 7677-24-9 ]
  • [ 13837-45-1 ]
  • [ 27374-25-0 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 21, p. 4129 - 4135
  • 6
  • [ 27374-25-0 ]
  • [ 1227158-84-0 ]
  • [ 1227158-85-1 ]
YieldReaction ConditionsOperation in experiment
62% at 20℃; for 1.16667 h; Molecular sieve; Reflux Example 65
1-Cyclopropyl-4-{4-[(5-methyl-3-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]pyridin-2-yl}piperazine
66 ml (1.15 mmol) of glacial acetic acid, 13.9 g of dried, powdered molecular sieve (3 Å) and 139 ml (0.692) of 1-ethoxy-1-(trimethylsilyl)oxycyclopropane were added successively to a solution of 56.0 g (0.115 mol) of the compound from Example 64 in 1.13 l of methanol.
After stirring at RT for 10 min, 21.7 g (0.346 mol) of solid sodium cyanoborohydride were added.
The mixture was then heated under reflux for 1 h.
After cooling to RT, the undissolved material was filtered off with suction and the filtrate was concentrated on a rotary evaporator.
The residue obtained was taken up in 1 l of ethyl acetate and the mixture was washed twice with approx.
750 ml of saturated sodium bicarbonate solution each time and then with approx. 750 ml of saturated sodium chloride solution.
After drying over anhydrous sodium sulfate, the mixture was filtered and the filtrate was freed from the solvent on a rotary evaporator.
The residue (53 g) was recrystallized from a boiling mixture of 293 ml of ethanol and 59 ml of water.
When the crystallization was complete (after approx. 20 h at RT), the mixture was filtered with suction.
The solid was washed with 36 ml of ethanol/water (5:1) and then dried under a high vacuum. 26.4 g of the title compound were obtained as the first batch in this way.
The mother liquor of the crystallization was concentrated on a rotary evaporator.
A further 20.3 g of the product were obtained in the form of the formate salt by means of preparative HPLC (method N).
For liberation of the base, a suspension of this formate in 1 l of ethyl acetate was washed successively with approx.
200 ml each of saturated sodium bicarbonate solution, water and saturated sodium chloride solution.
After drying over anhydrous sodium sulfate, the mixture was filtered and the filtrate was freed from the solvent on a rotary evaporator.
The residue (13 g) was recrystallized from a boiling mixture of 80 ml of ethanol and 16 ml of water.
When the crystallization was complete (after approx. 4 h at RT), the mixture was filtered with suction and the solid was dried under a high vacuum.
A further 11.2 g of the title compound were obtained in this manner (yield in total 37.6 g, 62percent of th.).
Melting point: 140° C.
1H-NMR (400 MHz, CDCl3, δ/ppm): 8.26 (d, 2H), 8.13 (d, 1H), 7.33 (d, 2H), 6.83 (s, 1H), 6.33 (d, 1H), 6.32 (s, 1H), 5.35 (s, 2H), 3.47 (dd, 4H), 2.69 (dd, 4H), 2.30 (s, 3H), 1.65-1.60 (m, 1H), 0.48-0.42 (m, 4H).
LC/MS (method D, ESIpos): Rt=1.91 min, m/z=526 [M+H]+.
Reference: [1] Patent: US2013/196964, 2013, A1, . Location in patent: Paragraph 1599; 1600; 1601; 1602; 1603
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