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Chemical Structure| 3006-96-0 Chemical Structure| 3006-96-0

Structure of 4-(Hydroxymethyl)benzoic acid
CAS No.: 3006-96-0

Chemical Structure| 3006-96-0

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Product Details of [ 3006-96-0 ]

CAS No. :3006-96-0
Formula : C8H8O3
M.W : 152.15
SMILES Code : C1=CC(=CC=C1C(O)=O)CO
MDL No. :MFCD00017598
InChI Key :WWYFPDXEIFBNKE-UHFFFAOYSA-N
Pubchem ID :76360

Safety of [ 3006-96-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 3006-96-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 39.53
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

57.53 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.27
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.93
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.73
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.05
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.06
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.01

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.64
Solubility 3.48 mg/ml ; 0.0229 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.72
Solubility 2.87 mg/ml ; 0.0189 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.58
Solubility 3.97 mg/ml ; 0.0261 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.57 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.0

Application In Synthesis of [ 3006-96-0 ]

* 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.

  • Downstream synthetic route of [ 3006-96-0 ]

[ 3006-96-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 99-94-5 ]
  • [ 76-05-1 ]
  • [ 1642-81-5 ]
  • [ 100-21-0 ]
  • [ 5162-82-3 ]
  • [ 3006-96-0 ]
  • [ 619-66-9 ]
  • [ 78504-88-8 ]
  • 3
  • [ 6338-41-6 ]
  • [ 74-85-1 ]
  • [ 3006-96-0 ]
YieldReaction ConditionsOperation in experiment
21% With Sn-Beta molecular sieve; In 1,4-dioxane; at 190℃; under 52476.2 Torr; for 12h;High pressure; Autoclave; A series of experiments were conducted to test the variables related to the conversion of 5-hydroxymethyl-2-furoic acid (HMFA) to 4-hydroxymethylbenzoic acid (HMBA). This transformation is a key intermediate step in the transformation of hydroxymethyl furfural (HMF) to (purified) terephthalic acid (PTA), according to: The results are shown in Tables 8 and FIG. 9. Reaction conditions for FIG. 9 were 1000 psig ethylene at 190° C., 10 g of a 100 mM dioxane solution of HFMA, with 100 mg Sn-Beta catalyst. [TABLE-US-00008] TABLE 8 All reactions were run at 850-1000 psig total pressure, 190° C., 10 g of a 100 mM HFMA solution, 100 mg catalyst. HMFA HMBA HMBA Entry Catalyst Solvent Time (hr) Converson (percent) Yield (percent) Selectivity (percent) 1 Sn-Beta dioxane 0.5 18 4 22 2 Sn-Beta dioxane 2 36 11 31 3 Sn-Beta dioxane 4 57 15 26 4 Sn-Beta dioxane 6 61 19 31 5 Sn-Beta dioxane 12 76 21 28 dioxane/water 6 Sn-Beta 1:1 v/v 0.5 94 0 0 7 Sn-Beta THF+ 0.5 35 2 6 8 Zr-Beta dioxane 6 87 9 10 9 None dioxane 2 5 0 0 10 None dioxane 6 21 0 0 11 Si-Beta dioxane 2 20 0 0 12 Si-Beta dioxane 6 56 13 Si-MFI dioxane 2 25 0 0
19% In 1,4-dioxane; at 20 - 190℃; under 27752.8 - 52505.3 Torr; for 6h;Inert atmosphere; General procedure: Experiments were carried out in a 50-mL high pressure stainless steel batch reactor (Parr Series 4590) equipped with a magnetic stirrer and heater. The reactor setup allowed for ethylene gas(Matheson, 99.995percent purity) or helium to be charged to the reactor. In a typical experiment, 100 mg of catalyst and 10 g of a 0.1 M diene solution in dioxane (Sigma-Aldrich, 99.8percent) was loaded into the reactor. The magnetic stirrer was operated at 200 rpm and the head space of the reactor was purged with helium gas with a fill/vent cycle (10×). Next, the reactor was pressurized to 37 bar (room temperature) with ethylene gas, the inlet valve was closed, and the reaction was performed in batch operation. The reactor was heated to 190 °C within 15 min while the pressure increased autogenously to 70 bar. At the end of the reaction time, the reactor was allowed to cool to room temperature and the reactor gases were vented. The product was then collected for analysis.
  • 4
  • aminomethyl-terminated Tentagel resin [ No CAS ]
  • [ 3006-96-0 ]
  • [ 71989-23-6 ]
  • [ 145069-56-3 ]
  • C47H48N3O9Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
AM-PS (0.1 mmol, 118 mg, loading 0.85 mmol g-1) was swelled in DMF for 10 min. To a solution of Rink amide linker (217 mg, 0.4 mmol) and Cl-HOBt (68 mg,0.4 mmol) in DMF (3 mL) was added DIC (62 mul, 0.4 mmol) and the solution was added to the drained resin. The mixture was allowed to stand for 90 min, drained, and washed with DMF. The Kaiser test was negative. The Fmoc group was removed with 20% piperidine (25 min), washed with DMF, and a solution of HMBA (46 mg, 0.3 mmol), Cl-HOBt (101 mg,0.6 mmol), and DIC (63 muL, 0.4 mmol) was added. The reaction was left to proceed overnight, at which point a negative Kaiser test was obtained. Fmoc-Ile-OH (106 mg, 0.3 mmol) was dissolved in DMF (3 mL), DIC (63 muL, 0.4 mmol) was added, and the resultant solution was added to the resin. A solution of DMAP (122 muL, 10 mgmL-1, 0.01 mmol) was added and the mixture shaken for 1 h. The resin was drained and washed with DMF and the procedure repeated twice more to ensure complete esterification. Any remaining hydroxyl groups were capped with 20% (v/v) acetic anhydride in DMF with a catalytic amount of DMAP (0.01 mmol) for 30 min. A total of 203 mg of resin was collected, on which the peptide was elongated as described to afford resin-bound linear peptide. Cyclisation and resin cleavage afforded lassomycin-HMBA-NH2 (125 mg, 62% yield, 64% purity; m/z (ESI-MS) 500.7, (M+4H)4+ requires 500.8). Crude lassomycin-HMBA-NH2 (15 mg, 7.65 mmol) was dissolved in methanol (7.65 mL), cooled to 0 C, and NaOMe (165 mg, 3.06 mmol) was added to give a final concentrationof 0.4 M. The solution was stored at 0 C for 1 h, quenched with TFA (0.58 mL) to give a final TFA concentration of 1M, concentrated under a stream of nitrogen, dissolved in 50% aq.CH3CN containing 0.1 %TFA, and lyophilised. In parallel, a second portion (14 mg) was also subjected to the above conditions. Pooling of both batches and purification by HPLC afforded lassomycin-OMe 1 (4.12 mg, 20% yield). m/z (ESI-MS) 470.9, (M+4H)4+ requires 471.0; 627.5, (M+3H)3+ requires 627.7. Deconvolution yields a mass of 1879.60.07 Da. The calculated mass is 1880.2 Da.
  • 5
  • aminomethylpolystyrene [ No CAS ]
  • [ 35661-60-0 ]
  • [ 3006-96-0 ]
  • [ 145069-56-3 ]
  • C53H52N3O9Pol [ No CAS ]
 

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