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Product Details of [ 72657-23-9 ]

CAS No. :72657-23-9 MDL No. :MFCD00063450
Formula : C5H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ATCCIZURPPEVIZ-SCSAIBSYSA-N
M.W : 118.13 Pubchem ID :5324733
Synonyms :

Calculated chemistry of [ 72657-23-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 28.6
TPSA : 46.53 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) : -7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : -0.06
Log Po/w (WLOGP) : -0.21
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : 0.02
Consensus Log Po/w : 0.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.34
Solubility : 54.4 mg/ml ; 0.461 mol/l
Class : Very soluble
Log S (Ali) : -0.47
Solubility : 40.4 mg/ml ; 0.342 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.17
Solubility : 79.9 mg/ml ; 0.676 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 72657-23-9 ]

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 [ 72657-23-9 ]

* 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 [ 72657-23-9 ]
  • Downstream synthetic route of [ 72657-23-9 ]

[ 72657-23-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 15484-46-5 ]
  • [ 80657-57-4 ]
  • [ 72657-23-9 ]
YieldReaction ConditionsOperation in experiment
58 % ee With (cycloocta-1,5-diene)-[(S,S)-2,2'-bis(ferrocenyl-phenylphosphino)-1,1'-biphenyl] rhodium tetrafluoroborate; hydrogen In dichloromethane at 20℃; for 16 h; Autoclave K.3. Asymmetric catalyzed hydrogenationTypical procedure A solution of [Rh(COD)L*]BF4 (0.005 mmol, 1 molpercent) and substrate (0.5 mmol) in dry solvent (7.5 mL) was introduced in a stainless steel autoclave. The autoclave was closed, purged with hydrogen and then pressurized with hydrogen. After 16h of stirring at room temperature, the pressure was released to atmospheric pressure and the solution was transferred to a round bottom flask. The solvent was removed on a rotary evaporator to give a residue which was purified by column chromatography on silica gel to afford the hydrogenated product. The enantiomeric excess was determined by HPLC on chiral column.Results of aymmetric catalyzed hydrogenations by rhodium complexes of ligands (1-48) or (1-49) are presented in table 9 and 10. Table 9. Asymmetric catalyzed hydrogenation by rhodium complexes of ligands (1-48)Substrate Diphosphine 48 Cond. (RT 16h) ProductR R2 R R8 Solvant P Conv ee(¾) (percent) (percent)63 48a Ph oAn Ph Ph MeOH 4 64 93 61 (R)10 100 63 (R)20 100 60 (R)THF 10 6 ndCH2C12 7 nd Table 10. Asymmetric catalyzed hydrogenation by rhodium complex of ligand (I'-49c)
Reference: [1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 1-2, p. 185 - 189
[2] Advanced Synthesis and Catalysis, 2007, vol. 349, # 10, p. 1592 - 1596
[3] Advanced Synthesis and Catalysis, 2007, vol. 349, # 10, p. 1592 - 1596
[4] Tetrahedron Asymmetry, 2009, vol. 20, # 2, p. 210 - 213
[5] Advanced Synthesis and Catalysis, 2008, vol. 350, # 10, p. 1610 - 1614
[6] Angewandte Chemie - International Edition, 2009, vol. 48, # 12, p. 2162 - 2165
[7] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2525 - 2532
[8] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2525 - 2532
[9] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2533 - 2543
[10] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2533 - 2543
[11] Chemistry - A European Journal, 2009, vol. 15, # 39, p. 10272 - 10279
[12] Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2663 - 2666
[13] Tetrahedron Asymmetry, 2010, vol. 21, # 21-22, p. 2671 - 2674
[14] Organometallics, 2011, vol. 30, # 24, p. 6718 - 6725
[15] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[16] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[17] Advanced Synthesis and Catalysis, 2012, vol. 354, # 1, p. 59 - 64
[18] Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 1949 - 1960
[19] Chemistry - A European Journal, 2012, vol. 18, # 33, p. 10368 - 10381
[20] Chemistry - A European Journal, 2012, vol. 18, # 33, p. 10368 - 10381
[21] European Journal of Organic Chemistry, 2012, # 26, p. 4963 - 4968
[22] European Journal of Inorganic Chemistry, 2012, # 29, p. 4684 - 4693
[23] Patent: WO2013/7724, 2013, A1, . Location in patent: Page/Page column 88; 89; 90
[24] Advanced Synthesis and Catalysis, 2014, vol. 356, # 4, p. 795 - 804
[25] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1775 - 1786
[26] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1775 - 1786
[27] ChemBioChem, 2017, vol. 18, # 7, p. 685 - 691
  • 2
  • [ 64809-29-6 ]
  • [ 80657-57-4 ]
  • [ 72657-23-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2533 - 2543
[2] ChemPlusChem, 2014, vol. 79, # 8, p. 1103 - 1108
  • 3
  • [ 186581-53-3 ]
  • [ 1910-47-0 ]
  • [ 80657-57-4 ]
  • [ 72657-23-9 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 12, p. 2400 - 2404
  • 4
  • [ 72657-23-9 ]
  • [ 110556-33-7 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 3, p. 337 - 340
  • 5
  • [ 72657-23-9 ]
  • [ 98190-85-3 ]
  • [ 110556-33-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 8, p. 1519 - 1528
  • 6
  • [ 15484-46-5 ]
  • [ 72657-23-9 ]
YieldReaction ConditionsOperation in experiment
> 90 % ee With flavin mononucleotide; alpha-D-glucopyranose; glucose dehydrogenase from Thermoplasma acidophilum; old yellow enzyme 1 from Saccharomyces pastorianus; nicotinamide adenine dinucleotide phosphate In aq. buffer at 20℃; for 24 h; Enzymatic reaction General procedure: Ene-reductase activity assays were performed at ambient temperature under anaerobic conditions (Coy Laboratory, Grass Lake, MI). For preparing reaction stock solution, individual substrates (see below) were dissolved in 50mM Tris–HCl (pH 7.5), supplemented with 200μM NADP+, 100mM glucose, and glucose dehydrogenase (GDH) from Thermoplasma acidophilum (2 units for IVTT reactions, 5 units for purified enzyme reactions). Individual substrate concentrations were chosen to ensure vmax conditions or maximum solubility. At these substrate levels, reaction times were adjusted for 10–50percent substrate conversion. To assay OYE activity in IVTT experiments, 20μL of the reaction stock solution was mixed with 2–10μL IVTT reaction mixture and the total assay volume was adjusted to 30μl with 50mM Tris–HCl (pH 7.5). To assay purified OYE1 variants, the enzyme (final concentration: 250nM) was added to 500μl reaction stock solution. Reaction progress was monitored by removing 30-μl aliquots from the assay solution and quenching them by mixing thoroughly with 30μL of ethyl acetate containing 1mM cyclohexanone as internal standard. A sample of the organic phase was collected and analyzed by GC (protocols: see below). The enantio/diasteriomeric excess were calculated by integration of product and substrate peak areas. Relative rates of conversion for individual substrates were calculated by dividing the measured rate of conversion for OYE1 variant over the corresponding rate for wild type OYE1.
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1775 - 1786
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 2, p. 210 - 213
[3] Angewandte Chemie - International Edition, 2009, vol. 48, # 12, p. 2162 - 2165
[4] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2533 - 2543
[5] Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2663 - 2666
[6] Tetrahedron Asymmetry, 2010, vol. 21, # 21-22, p. 2671 - 2674
[7] Tetrahedron, 2016, vol. 72, # 46, p. 7282 - 7287
[8] ChemBioChem, 2017, vol. 18, # 7, p. 685 - 691
  • 7
  • [ 212051-35-9 ]
  • [ 72657-23-9 ]
YieldReaction ConditionsOperation in experiment
72% With t-butyl bromide In acetonitrile for 0.833333 h; Reflux General procedure: To asolution of the PMB ether (1 mmol) in acetonitrile (10 mL), t-BuBr (1.1 equiv)was added and stirred at reflux. After completion of the reaction (monitored byTLC), it was concentrated under reduced pressure and the resulting crude wasdissolved in ethyl acetate (50 mL) and washed with saturated sodiumhydrogenocarbonate (25 mL). The aqueous layer was extracted with ethylacetate (2 5 mL) and the combine organic layer was washed with brinesolution, dried (MgSO4), concentrated under reduced pressure and the residuewas purified by column chromatography (silica gel, EtOAc, cyclohexane) toafford the corresponding alcohol.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 49, p. 6823 - 6826
  • 8
  • [ 15484-46-5 ]
  • [ 80657-57-4 ]
  • [ 72657-23-9 ]
YieldReaction ConditionsOperation in experiment
58 % ee With (cycloocta-1,5-diene)-[(S,S)-2,2'-bis(ferrocenyl-phenylphosphino)-1,1'-biphenyl] rhodium tetrafluoroborate; hydrogen In dichloromethane at 20℃; for 16 h; Autoclave K.3. Asymmetric catalyzed hydrogenationTypical procedure A solution of [Rh(COD)L*]BF4 (0.005 mmol, 1 molpercent) and substrate (0.5 mmol) in dry solvent (7.5 mL) was introduced in a stainless steel autoclave. The autoclave was closed, purged with hydrogen and then pressurized with hydrogen. After 16h of stirring at room temperature, the pressure was released to atmospheric pressure and the solution was transferred to a round bottom flask. The solvent was removed on a rotary evaporator to give a residue which was purified by column chromatography on silica gel to afford the hydrogenated product. The enantiomeric excess was determined by HPLC on chiral column.Results of aymmetric catalyzed hydrogenations by rhodium complexes of ligands (1-48) or (1-49) are presented in table 9 and 10. Table 9. Asymmetric catalyzed hydrogenation by rhodium complexes of ligands (1-48)Substrate Diphosphine 48 Cond. (RT 16h) ProductR R2 R R8 Solvant P Conv ee(¾) (percent) (percent)63 48a Ph oAn Ph Ph MeOH 4 64 93 61 (R)10 100 63 (R)20 100 60 (R)THF 10 6 ndCH2C12 7 nd Table 10. Asymmetric catalyzed hydrogenation by rhodium complex of ligand (I'-49c)
Reference: [1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 1-2, p. 185 - 189
[2] Advanced Synthesis and Catalysis, 2007, vol. 349, # 10, p. 1592 - 1596
[3] Advanced Synthesis and Catalysis, 2007, vol. 349, # 10, p. 1592 - 1596
[4] Tetrahedron Asymmetry, 2009, vol. 20, # 2, p. 210 - 213
[5] Advanced Synthesis and Catalysis, 2008, vol. 350, # 10, p. 1610 - 1614
[6] Angewandte Chemie - International Edition, 2009, vol. 48, # 12, p. 2162 - 2165
[7] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2525 - 2532
[8] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2525 - 2532
[9] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2533 - 2543
[10] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2533 - 2543
[11] Chemistry - A European Journal, 2009, vol. 15, # 39, p. 10272 - 10279
[12] Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2663 - 2666
[13] Tetrahedron Asymmetry, 2010, vol. 21, # 21-22, p. 2671 - 2674
[14] Organometallics, 2011, vol. 30, # 24, p. 6718 - 6725
[15] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[16] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[17] Advanced Synthesis and Catalysis, 2012, vol. 354, # 1, p. 59 - 64
[18] Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 1949 - 1960
[19] Chemistry - A European Journal, 2012, vol. 18, # 33, p. 10368 - 10381
[20] Chemistry - A European Journal, 2012, vol. 18, # 33, p. 10368 - 10381
[21] European Journal of Organic Chemistry, 2012, # 26, p. 4963 - 4968
[22] European Journal of Inorganic Chemistry, 2012, # 29, p. 4684 - 4693
[23] Patent: WO2013/7724, 2013, A1, . Location in patent: Page/Page column 88; 89; 90
[24] Advanced Synthesis and Catalysis, 2014, vol. 356, # 4, p. 795 - 804
[25] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1775 - 1786
[26] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1775 - 1786
[27] ChemBioChem, 2017, vol. 18, # 7, p. 685 - 691
  • 9
  • [ 64809-29-6 ]
  • [ 80657-57-4 ]
  • [ 72657-23-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2533 - 2543
[2] ChemPlusChem, 2014, vol. 79, # 8, p. 1103 - 1108
  • 10
  • [ 186581-53-3 ]
  • [ 1910-47-0 ]
  • [ 72657-23-9 ]
Reference: [1] Tetrahedron Letters, 1981, vol. 22, # 37, p. 3555 - 3556
  • 11
  • [ 186581-53-3 ]
  • [ 1910-47-0 ]
  • [ 80657-57-4 ]
  • [ 72657-23-9 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 12, p. 2400 - 2404
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