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[ CAS No. 4704-94-3 ] {[proInfo.proName]}

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Chemical Structure| 4704-94-3
Chemical Structure| 4704-94-3
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Product Details of [ 4704-94-3 ]

CAS No. :4704-94-3 MDL No. :MFCD00192217
Formula : C4H10O3 Boiling Point : -
Linear Structure Formula :(HOCH2)2CHCH2OH InChI Key :SFRDXVJWXWOTEW-UHFFFAOYSA-N
M.W : 106.12 Pubchem ID :78432
Synonyms :

Calculated chemistry of [ 4704-94-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 24.83
TPSA : 60.69 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) : -8.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.72
Log Po/w (XLOGP3) : -1.57
Log Po/w (WLOGP) : -1.42
Log Po/w (MLOGP) : -1.06
Log Po/w (SILICOS-IT) : -0.65
Consensus Log Po/w : -0.8

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.69
Solubility : 519.0 mg/ml ; 4.89 mol/l
Class : Highly soluble
Log S (Ali) : 0.8
Solubility : 675.0 mg/ml ; 6.36 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.65
Solubility : 475.0 mg/ml ; 4.48 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 4704-94-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4704-94-3 ]

* 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 [ 4704-94-3 ]
  • Downstream synthetic route of [ 4704-94-3 ]

[ 4704-94-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 4704-94-3 ]
  • [ 77-76-9 ]
  • [ 4728-12-5 ]
YieldReaction ConditionsOperation in experiment
99% at 20℃; (2, 2-Dimethyl-fl, 3] dioxan- 5 -yl) -methanol[0682] A solution of 2,2-dimethoxypropane (5.88 g, 56.5 mmol), 2-methyl- propane-l,3-diol (5.0 g, 47 mmol), and PTSA monohydrate (0.48 g, 2.3 mmol) in THF (100 mL) was stirred O/N at rt. The mixture was concentrated in vacuo to give the title compound as a colorless liquid: yield 6.87 g (99percent).[0683] 1H NMR (400 MHz, CDCl3) δ (ppm): 4.03 (dd, J= 11.7, 3.5 Hz, 2H), 3.84- 3.73 (m, 4H), 2.49-2.39 (m, IH), 1.90-1.80 (m, IH), 1.45 (s, 3H), 1.40 (s, 3H).
95%
Stage #1: With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 3 h;
Stage #2: With triethylamine In tetrahydrofuran
To tetrahydrofuran suspension (150 ml) of 13 (4.90 g, 46.17 mmol), acetone dimethyl acetal (6.56 ml, 53.54 mmol) and toluene sulfonic acid hydrate (0.26 g, 1.39 mmol) were added while shaking at room temperature, and stirred for 3 hours at room temperature.
The reaction mixture was added triethylamine (3 ml), and evaporated to dryness under reduced pressure.
The residue was purified by silica gel column chromatography (solvent: chloroform/methanol = 10/1), to obtain 14 (6.38 g, 95percent) of oily colorless substance. APCI-MS m/z 147[M+H]+
91% With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 2 h; To a 100 mL round bottomed flask equipped with a magnetic stir bar containing THF (75 mL) was placed a (4 g, 38 mmol, 1 equiv). To this solution was added b (4.5 g, 43 mmol, 1.15 equiv), PTSA (0.2 g, 1.1 mmol, 0.03 equiv) and the reaction was allowed to stir at room temperature for 2 h. After the reaction was complete, solvent was removed in vacuo. The residue was purified over silica gel. Product eluted out in 60percent EtOAc:Hexanes mixture in a gradient elution on a Combiflash purification system. Isolated 86 (5 g, 91percent) as a colorless oil. MS: [M+H]+: 147.
73% at 20℃; for 51 h; Example 25 1 -(3 -(3 -hvdroxy-2-(hvdroxymethyl)propoxy)-4-methyl- 1 -phenyl- 1 H-pyrazol-5-yl)-3 -(2- phenyl-8-(trifluoromethyl)imidazo[ 1 ,2-a]pyridin-3-yl)urea [00651] Step A: Preparation of (2,2-dimethyl-l,3-dioxan-5-yl)methanol: To a suspension of 2-(hydroxymethyl)propane-l,3-diol (5.0 g, 47.1 mmol) in THF (100 mL) was added pTsOH (269 mg, 1.41 mmol) followed by 2,2-dimethoxypropane (6.72 mL, 54.7 mmol). The solution was stirred for 3 hours at ambient temperature then treated with pTsOH (200 mg) and stirred at ambient temperature for 48 hours. Triethylamine (3 mL) was added and the mixture concentrated under vacuum. The residue was purified silica column chromatography eluting with 5percent MeOH/DCM to afford (2,2-dimethyl-l,3-dioxan-5- yl)methanol (5.04 g, 73percent yield) as a colorless liquid. 1H NMR (CDC13) δ 4.02 (dd, J = 12.0, 4.1 Hz, 2H), 3.74-3.80 (m, 4H), 1.90 (t, J= 5.1 Hz, 1H), 1.78-1.88 (m, 1H), 1.45 (s, 3H), 1.40 (s, 3H) ppm.
44% With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 60 h; 2-(Hydroxymethyl)-1 ,3-propanediol (1.0 g, 9.4 mmol), 2,2-bis(methyloxy)propane (2.3 ml_, 18.8 mmol) and p-toluenesulfonic acid monohydrate (0.09 g, 0.5 mmol) were <n="69"/>dissolved in THF and stirred for -60 h. To the solution was added triethyl amine (1.0 ml.) and the solvent was evaporated. Purification was accomplished by column chromatography (CH2CI2: MeOH) to afford the title compound (0.6 g, 44percent) as a oil. 1H NMR (400 MHz, DMSOd6): δ ppm 4.52 (t, 1 H), 3.80 (dd, 2 H), 3.59 (dd, 2 H), 3.36 (dd, 2 H), 1.63 - 1.72 (m, 1 H), 1.28 (d, 6 H).

Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 26, p. 5694 - 5709
[2] Patent: WO2008/157726, 2008, A1, . Location in patent: Page/Page column 210
[3] Patent: EP2103611, 2009, A1, . Location in patent: Page/Page column 51-52
[4] Patent: WO2008/124703, 2008, A2, . Location in patent: Page/Page column 84
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 187 - 196
[6] Patent: WO2014/78408, 2014, A1, . Location in patent: Paragraph 00651
[7] Patent: WO2008/154271, 2008, A1, . Location in patent: Page/Page column 67-68
[8] Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5980 - 5988
[9] European Journal of Organic Chemistry, 2006, # 3, p. 719 - 728
[10] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3952 - 3954
[11] Patent: WO2006/79916, 2006, A1, . Location in patent: Page/Page column 91
[12] Patent: WO2008/63912, 2008, A1, . Location in patent: Page/Page column 54
[13] Patent: WO2008/86122, 2008, A2, . Location in patent: Page/Page column 75
[14] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 239 - 250
[15] Patent: WO2009/129385, 2009, A1, . Location in patent: Page/Page column 84
[16] Patent: US2009/291962, 2009, A1, . Location in patent: Page/Page column 17-18
[17] Patent: EP2079711, 2010, B1, . Location in patent: Page/Page column 29
[18] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 7, p. 321 - 325
[19] Organic Process Research and Development, 2012, vol. 16, # 9, p. 1527 - 1537
[20] Patent: WO2008/157330, 2008, A1, . Location in patent: Page/Page column 67
  • 2
  • [ 4704-94-3 ]
  • [ 67-64-1 ]
  • [ 4728-12-5 ]
YieldReaction ConditionsOperation in experiment
85.8%
Stage #1: With perchloric acid In water at 20℃; for 21 h;
Stage #2: With ammonium hydroxide In water
A mixture of 2-(hydroxymethyl)-1,3-propanediol (4.09 g, 38.5 mmol), acetone (130 ml, 1768 mmol) and 70percent perchloric acid (1.37 g, 9.55 mmol) was stirred at room temperature for 21 hours. After the pH of the reaction mixture was adjusted with concentrated aqueous ammonia to 9, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (silica gel: 100 g, elution solvent: heptane, heptane/ethyl acetate=1/3) to obtain the title compound (4.83 g, yield: 85.8percent) as a colorless oil. 1H NMR(400 MHz, DMSO-d6) δppm; 1.29(3H, s), 1.30(3H, s), 1.64-1.74(1H, m), 3.35-3.41(2H, m), 3.61(2H, dd, J=7, 12 Hz), 3.82(2H, dd, J=4, 12 Hz), 4.54(1H, t, J=5 Hz).
85.8% With perchloric acid In water at 20℃; for 21 h; A mixture of 2-(hydroxymethyl)-1,3-propanediol (4.09 g, 38.5 mmol), acetone (130 ml, 1.768 mmol) and 70percent perchloric acid (1.37 g, 9.55 mmol) was stirred for 21 hours at room temperature. The reaction mixture was concentrated after adjusting to pH 9 with concentrated ammonia. The residue was purified by silica gel column chromatography (silica gel: 100 g, elution solvent: heptane, heptane/ethyl acetate = 1/3) to obtain the target compound (4.83 g, yield: 85.8percent) as a colorless oily substance. 1H-NMR (400 MHz, DMSO-d6) δppm: 1.29 (3H,s), 1.30 (3H,s), 1.64-1.74 (1H,m), 3.35-3.41 (2H,m), 3.61 (2H,dd,J=7,12 Hz), 3.82 (2H,dd,J=4,12 Hz), 4.54 (1H,t,J=5 Hz)
85.8% With perchloric acid In water at 20℃; for 21 h; (Production Example 1) (2,2-dimethyl-1,3-dioxan-5-yl)methanol [Show Image] A mixture of 2-(hydroxymethyl)-1,3-propanediol (4.09 g, 38.5 mmol), acetone (130 ml, 1768 mmol) and 70percent perchloric acid (1.37 g, 9.55 mmol) was stirred for 21 hours at room temperature. The pH of the reaction mixture was adjusted to 9 with concentrated aqueous ammonia and the reaction mixture was concentrated. The residue was purified by silica gel column chromatography (silica gel: 100 g, elution solvent: heptane, heptane/ethyl acetate= 1/3) to produce the title compound (4.83 g, yield: 85.8percent) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm; 1.29 (3H, s), 1.30 (3H, s), 1.64-1.74 (1H, m), 3.35-3.41 (2H, m), 3.61 (2H, dd, J=7, 12Hz), 3.82 (2H, dd, J=4, 12Hz), 4.54 (1H, t, J=5Hz).
85.8% at 20℃; for 21 h; (1 ) (2.2-Dimethyl-1.3-dioxan-5-vπmethanolA mixture of 2-(hydroxymethyl)-1 ,3-propanedior(4.09 g, 38.5 mmol), acetone (130 ml, 1768 mmol), and 70percent perchloric acid (1.37 g, 9.55 mmol) was stirred at room temperature for 21 hours. A pH of the reaction mixture was adjusted to 9 using concentrated ammonia water, and then subjected to concentration. The residue was purified by silica gel column chromatography (silica gel: 100 g, eluent: heptane, heptane / ethyl acetate = 1 / 3), whereby the title compound (4.83 g, percentage yield 85.8percent) was obtained as a colorless oil. 1H-NMR (400 MHz, DMSO-d6) δ ppm: 1.29 (3H, s), 1.30 (3H, s), 1.64-1.74 (1 H, m), 3.35-3.41 (2H1 m), 3.61 (2H, dd, J = 7, 12 Hz), 3.82 (2H, dd, J = 4, 12 Hz), 4.54 (1 H, t, J = 5 Hz).

Reference: [1] Patent: US2007/10542, 2007, A1, . Location in patent: Page/Page column 38
[2] Patent: EP2065379, 2009, A1, . Location in patent: Page/Page column 18-19
[3] Patent: EP2077265, 2009, A1, . Location in patent: Page/Page column 15
[4] Patent: WO2008/47849, 2008, A1, . Location in patent: Page/Page column 38
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 20, p. 2909 - 2914
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 20, p. 6104 - 6107
[7] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 15, p. 4008 - 4030
[8] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7539 - 7554
  • 3
  • [ 113967-50-3 ]
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YieldReaction ConditionsOperation in experiment
90% With sodium methylate In methanol for 20 h; Reflux The white powder obtained in the step (2) (360 g, 0.86 mol) was dissolved in methanol (2 L), sodium methoxide (139 g, 2.58 mol) was added, and the reaction system was heated to reflux for 20 hours.The solvent was evaporated, the residue was taken twice with chloroform, the organic phases were combined, dried and concentrated.The combined organic phases were dried, concentrated, crystallized isobutanol to give 82g white powder, yield 90percent.
Reference: [1] Synthesis, 1987, # 8, p. 742 - 744
[2] Patent: CN108440455, 2018, A, . Location in patent: Paragraph 0066; 0076-0078; 0100; 0122
  • 4
  • [ 555-43-1 ]
  • [ 4704-94-3 ]
  • [ 57-11-4 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 16 - 24
  • 5
  • [ 555-44-2 ]
  • [ 4704-94-3 ]
  • [ 57-10-3 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 16 - 24
  • 6
  • [ 122-32-7 ]
  • [ 112-80-1 ]
  • [ 4704-94-3 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 16 - 24
  • 7
  • [ 40364-80-5 ]
  • [ 4704-94-3 ]
Reference: [1] Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1393 - 1403
[2] Patent: US4336408, 1982, A,
  • 8
  • [ 465540-17-4 ]
  • [ 4704-94-3 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 22, p. 4037 - 4039
  • 9
  • [ 6279-86-3 ]
  • [ 4704-94-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 1, p. 187 - 196
[2] Chemische Berichte, 1955, vol. 88, p. 1511,1516,1518
  • 10
  • [ 50-00-0 ]
  • [ 107-02-8 ]
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  • [ 504-63-2 ]
Reference: [1] Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1393 - 1403
  • 11
  • [ 50-00-0 ]
  • [ 75-07-0 ]
  • [ 115-77-5 ]
  • [ 2163-42-0 ]
  • [ 4704-94-3 ]
  • [ 504-63-2 ]
Reference: [1] Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1393 - 1403
[2] Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1393 - 1403
  • 12
  • [ 50-00-0 ]
  • [ 75-07-0 ]
  • [ 68516-39-2 ]
  • [ 115-77-5 ]
  • [ 4704-94-3 ]
  • [ 2831-90-5 ]
  • [ 68658-38-8 ]
  • [ 504-63-2 ]
Reference: [1] Liebigs Annalen der Chemie, 1985, # 5, p. 1082 - 1087
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