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[ CAS No. 95124-07-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 95124-07-5
Chemical Structure| 95124-07-5
Chemical Structure| 95124-07-5
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Product Details of [ 95124-07-5 ]

CAS No. :95124-07-5 MDL No. :MFCD00077856
Formula : C8H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :PWQAXFWWMXTVFT-UHFFFAOYSA-N
M.W : 170.16 Pubchem ID :4620160
Synonyms :

Calculated chemistry of [ 95124-07-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.3
TPSA : 52.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 0.75
Log Po/w (WLOGP) : 0.05
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : 0.83
Consensus Log Po/w : 0.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.04
Solubility : 15.6 mg/ml ; 0.0917 mol/l
Class : Very soluble
Log S (Ali) : -1.43
Solubility : 6.26 mg/ml ; 0.0368 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.56
Solubility : 46.5 mg/ml ; 0.274 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.29

Safety of [ 95124-07-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 95124-07-5 ]

* 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 [ 95124-07-5 ]
  • Downstream synthetic route of [ 95124-07-5 ]

[ 95124-07-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 95124-07-5 ]
  • [ 14035-96-2 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 11, p. 2195 - 2198
  • 2
  • [ 95124-07-5 ]
  • [ 14035-96-2 ]
  • [ 40637-56-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 18, p. 3544 - 3552
  • 3
  • [ 106-96-7 ]
  • [ 108-59-8 ]
  • [ 95124-07-5 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: at 0 - 20℃; for 1.25 h;
Stage #2: at 0 - 20℃;
General procedure: Small Na pieces (2.30 g, 100 mmol) were carefully added to EtOH (100 mL) at room temperature. After the EtONa solution prepared was cooled to 0 °C, diethyl malonate (16.0 g, 100 mmol) was added to the stirred solution over 10 min. After 15 min the solution was warmed to room temperature and stirred for 50 min. The enolate solution was recooled to 0°C, and 3-bromopropyne (11.9 g, 100 mmol) was added over 20 min. After 30 min the solution was warmed to room temperature and stirred overnight. The reaction mixture was evaporated and washed with H2O. The aqueous layer was extracted two times with Et2O. The combined organic layer was dried over Na2SO4 and evaporated. Purification of the residual oil by distillation and silica-gel column chromatography (hexane-AcOEt 10:1) gave diethyl (prop-2-ynyl)malonate (11.9 g, 60.0 mmol) in 60percent yield. 1 The product was also prepared from triethyl sodiomethanetricarb-oxylate and 3-bromopropyne. 2 Diethyl (prop-2-ynyl)malonate:
38% With potassium carbonate In acetone; tolueneReflux A round-bottomed flask containing powdered potassium carbonate (2.76 g, 20 mmol) was charged with dry acetone (20 mL) and dimethyl malonate (2.64 g, 20 mmol). The suspension was warmed to reflux and propargyl bromide 80percent in toluene (0.952 g, 8 mmol, 0.4 equiv) was added dropwise. The reaction was stirred overnight at reflux. Then, this mixture was cooled to room temperature and filtered over celite®. The solution was concentrated at reduced pressure (volatile product, T = 40 °C, P ≥ 400 mbar). The pure product was isolated as colorless liquid after purification by column chromatography (PE/Et2O = 90/10 – 80/20 – 70/30) (515 mg, 38percent).
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 30, p. 7913 - 7917[2] Angew. Chem., 2014, vol. 126, # 30, p. 8047 - 8051,5
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 12, p. 2007 - 2011
[4] Chemical Communications, 2014, vol. 50, # 5, p. 593 - 595
[5] Organic Letters, 2013, vol. 15, # 3, p. 582 - 585
[6] Organic Letters, 2002, vol. 4, # 3, p. 383 - 386
[7] Chemistry - A European Journal, 2014, vol. 20, # 3, p. 801 - 810
[8] Tetrahedron Letters, 2016, vol. 57, # 46, p. 5065 - 5069
[9] Organic Letters, 2017, vol. 19, # 4, p. 802 - 805
[10] Tetrahedron, 1998, vol. 54, # 32, p. 9373 - 9392
[11] Chemistry - A European Journal, 2017, vol. 23, # 71, p. 17862 - 17866
[12] Tetrahedron, 1985, vol. 41, # 24, p. 5797 - 5802
[13] Synthetic Communications, 1986, vol. 16, # 3, p. 291 - 298
[14] Tetrahedron Letters, 1996, vol. 37, # 39, p. 7027 - 7030
[15] Chemistry - A European Journal, 2005, vol. 11, # 8, p. 2577 - 2590
[16] Tetrahedron Letters, 2018, vol. 59, # 2, p. 103 - 107
[17] Advanced Synthesis and Catalysis, 2016, vol. 358, # 12, p. 1916 - 1923
[18] Tetrahedron, 1991, vol. 47, # 32, p. 6189 - 6196
[19] Journal of Organometallic Chemistry, 1987, vol. 334, p. 57 - 76
[20] Chemical Communications, 2009, # 26, p. 3916 - 3918
[21] Angewandte Chemie - International Edition, 2013, vol. 52, # 18, p. 4883 - 4886[22] Angew. Chem., 2013, vol. 125, # 18, p. 5056
[23] Journal of Organic Chemistry, 2014, vol. 79, # 3, p. 1399 - 1405
[24] Organic and Biomolecular Chemistry, 2015, vol. 13, # 2, p. 612 - 619
[25] Journal of Organic Chemistry, 2017, vol. 82, # 16, p. 8743 - 8751
  • 4
  • [ 1180611-55-5 ]
  • [ 95124-07-5 ]
Reference: [1] Chemical Communications, 2009, # 26, p. 3916 - 3918
  • 5
  • [ 23418-85-1 ]
  • [ 108-59-8 ]
  • [ 95124-07-5 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 20, p. 4548 - 4551
  • 6
  • [ 659-86-9 ]
  • [ 108-59-8 ]
  • [ 95124-07-5 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 24, p. 5389 - 5392
  • 7
  • [ 624-65-7 ]
  • [ 108-59-8 ]
  • [ 95124-07-5 ]
Reference: [1] Chemical Communications, 2008, # 25, p. 2923 - 2925
  • 8
  • [ 18424-76-5 ]
  • [ 106-96-7 ]
  • [ 98198-39-1 ]
  • [ 4431-32-7 ]
  • [ 63104-44-9 ]
  • [ 95124-07-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 1215 - 1224
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