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[ CAS No. 4254-14-2 ] {[proInfo.proName]}

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Chemical Structure| 4254-14-2
Chemical Structure| 4254-14-2
Structure of 4254-14-2 * Storage: {[proInfo.prStorage]}

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Product Details of [ 4254-14-2 ]

CAS No. :4254-14-2 MDL No. :MFCD00066248
Formula : C3H8O2 Boiling Point : -
Linear Structure Formula :HOCH(CH3)CH2OH InChI Key :DNIAPMSPPWPWGF-GSVOUGTGSA-N
M.W : 76.09 Pubchem ID :259994
Synonyms :
Chemical Name :(R)-Propane-1,2-diol

Calculated chemistry of [ 4254-14-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 18.86
TPSA : 40.46 ?2

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) : -7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.93
Log Po/w (XLOGP3) : -0.92
Log Po/w (WLOGP) : -0.64
Log Po/w (MLOGP) : -0.63
Log Po/w (SILICOS-IT) : -0.54
Consensus Log Po/w : -0.36

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.33
Solubility : 164.0 mg/ml ; 2.16 mol/l
Class : Highly soluble
Log S (Ali) : 0.55
Solubility : 272.0 mg/ml ; 3.58 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.56
Solubility : 275.0 mg/ml ; 3.61 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 4254-14-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4254-14-2 ]

* 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 [ 4254-14-2 ]

[ 4254-14-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 4254-14-2 ]
  • [ 105-58-8 ]
  • [ 16606-55-6 ]
YieldReaction ConditionsOperation in experiment
90% at 105 - 110℃; for 8 h; Large scale R - Preparation of propylene carbonate,R-1,2-propanediol was added to a glass-lined reactor(38.05 kg, 500Mol),Diethyl carbonate(70.88 kg, 600 mol) and (3.4 kg, 50 mol) of sodium ethoxide,Heated to 105-110 ° C,Reaction for 8 hours,The reaction is terminated,The unreacted diethyl carbonate was distilled off under reduced pressure,Cooled to room temperature,Filter insoluble matter,The filtrate was evaporated to remove the solvent of product R - propylene carbonate 34.24 kg,Purity ≥ 99percentThe yield was 90percent.
81.2% With sodium methylate In ethanol at 80℃; Example 1
Preparation of (R)-4-methyl-1,3-dioxolan-2-one
To the mixture of diethyl carbonate (380 ml, 15.1 mol) and 200 g of (R)-1,2-propanediol was added 40 ml of denatured ethanol (the solution of 9 g sodium methoxide dissolved in 50 ml of anhydrous ethanol), the resulting solution was heated to 80° C., then ethanol was distilled off slowly.
The reaction process was monitored by TLC, after TLC showed that only trace amount of (R)-1,2-propanediol remained or (R)-1,2-propanediol was undetectable, ethanol was distilled under vacuum by water pump at 120° C. until no ethanol dropped out.
The residue was distilled under vacuum to give the title compound as a colorless transparent liquid (111 g, 81.2percent yield, purity 97percent by GC)
44.5 g With sodium ethanolate In ethanol at 80℃; The 1000 ml hydrogenation vessel was evacuated and then passed through nitrogen,Then add 500ml ethanol, 2g5percent Pd / C, 2.5g caustic soda, cool to -10 ,Slowly add 50g of S-glycidol,Then, hydrogen gas (about 2 atmospheres) was passed for 4 hours,To no longer consume hydrogen so far, filtered and concentrated to give 48 g of a colorless oil.
Reference： [1] Patent: CN105859781, 2016, A, . Location in patent: Paragraph 0011-0012
[2] Patent: US2010/216822, 2010, A1, . Location in patent: Page/Page column 13
[3] Tetrahedron Letters, 1998, vol. 39, # 14, p. 1853 - 1856
[4] Patent: EP1243590, 2002, A2, . Location in patent: Page 9
[5] Patent: CN102977146, 2016, B, . Location in patent: Paragraph 0016; 0021; 0023
[6] Patent: CN108358968, 2018, A, . Location in patent: Paragraph 0073; 0087-0089; 0134-0136; 0142-0144; 0150-0152
[7] Patent: JP2015/164934, 2015, A, . Location in patent: Paragraph 0166; 0167; 0173
  • 2
  • [ 4254-14-2 ]
  • [ 616-38-6 ]
  • [ 16606-55-6 ]
Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 23, p. 2931 - 2938
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