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Chemical Structure| 3236-48-4 Chemical Structure| 3236-48-4

Structure of 3236-48-4

Chemical Structure| 3236-48-4

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Product Details of [ 3236-48-4 ]

CAS No. :3236-48-4
Formula : C8H16O2
M.W : 144.21
SMILES Code : OC[C@H]1CC[C@H](CO)CC1
MDL No. :MFCD00066360
InChI Key :YIMQCDZDWXUDCA-UHFFFAOYSA-N
Pubchem ID :7735

Safety of [ 3236-48-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 3236-48-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 40.78
TPSA ?

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

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.88
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

0.57
Log Po/w (WLOGP)?

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

0.78
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.

0.9
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

1.21
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.07

Water Solubility

Log S (ESOL):?

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

-0.96
Solubility 15.8 mg/ml ; 0.109 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.

-0.99
Solubility 14.7 mg/ml ; 0.102 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

-0.72
Solubility 27.4 mg/ml ; 0.19 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.

-6.77 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.

0.55

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)

2.28

Application In Synthesis of [ 3236-48-4 ]

* 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 [ 3236-48-4 ]

[ 3236-48-4 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 3236-48-4 ]
  • [ 58811-11-3 ]
  • 3
  • [ 3399-22-2 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 4
  • [ 3399-21-1 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 5
  • [ 115506-09-7 ]
  • [ 1004-24-6 ]
  • [ 3236-48-4 ]
  • 6
  • [ 3236-48-4 ]
  • [ 108-24-7 ]
  • [ 10412-78-9 ]
  • 7
  • [ 3236-48-4 ]
  • [ 124-63-0 ]
  • [ 115506-09-7 ]
  • 8
  • [ 3236-48-4 ]
  • [ 124-63-0 ]
  • [ 98-59-9 ]
  • <i>trans</i>-1-methanesulfonyloxymethyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexane [ No CAS ]
  • 9
  • [ 828-51-3 ]
  • [ 3236-48-4 ]
  • C30H44O4 [ No CAS ]
  • 11
  • [ 3236-48-4 ]
  • [ 4942-47-6 ]
  • Adamantan-1-yl-acetic acid 4-(2-adamantan-1-yl-acetoxymethyl)-cyclohexylmethyl ester [ No CAS ]
  • 12
  • [ 3236-48-4 ]
  • [ 86198-29-0 ]
  • [ 100-64-1 ]
  • Acrylic acid 4-hydroxymethyl-cyclohexylmethyl ester [ No CAS ]
  • 13
  • [ 3236-48-4 ]
  • [ 23791-91-5 ]
  • 14
  • [ 3236-48-4 ]
  • [ 86218-00-0 ]
  • 15
  • [ 3236-48-4 ]
  • [ 75-03-6 ]
  • 4-(ethoxymethyl)-1-(hydroxymethyl)cyclohexane [ No CAS ]
  • 1,4-bis(ethoxymethyl)cyclohexane [ No CAS ]
  • 16
  • [ 3236-48-4 ]
  • [ 74-88-4 ]
  • [ 110928-47-7 ]
  • 17
  • [ 6308-18-5 ]
  • [ 3236-48-4 ]
  • cis-4-(hydroxymethyl)cyclohexylmethyl acetate [ No CAS ]
  • cis-4-(hydroxymethyl)cyclohexylmethyl acetate [ No CAS ]
  • 19
  • [ 3236-48-4 ]
  • [ 98-59-9 ]
  • [ 170811-08-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at -20 - 20℃; for 10h; Step 2: 4-Toluenesulfonyl chloride (742.5 g, 3.75 mol) was added to a solution of trans-cyclohexane-1,4-diyldimethanol (500 g, 4.17 mol) and Et3N (695 g, 5 mol) in DCM (6000 mL) at -20° C. The mixture was stirred at room temperature for 10 h and then quenched with water (10 L). The organic layer was separated, the aqueous layer was extracted with DCM (2*3 L), and the combined organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give trans-4-(hydroxymethyl)cyclohexylmethyl 4-methylbenzenesulfonate as a yellow oil.
  • 20
  • [ 3236-48-4 ]
  • [ 58479-61-1 ]
  • [ 194225-82-6 ]
  • 21
  • [ 3236-48-4 ]
  • [ 65967-52-4 ]
  • polymer, Mn 23500; diketene acetal (3,9-bis(ethylidene)-2,4,8,10-tetraoxaspiro<5,5>undecane); t-cyclohexane-1,4-dimethanol [ No CAS ]
  • 23
  • [ 3236-48-4 ]
  • [ 3282-30-2 ]
  • trans-4-(pivaloyloxymethyl)cyclohexanemethanol [ No CAS ]
  • 24
  • polymer, Mn 23500; diketene acetal (3,9-bis(ethylidene)-2,4,8,10-tetraoxaspiro<5,5>undecane); t-cyclohexane-1,4-dimethanol [ No CAS ]
  • [ 3236-48-4 ]
  • pentaerythritol dipropionate [ No CAS ]
  • 27
  • [ 3236-48-4 ]
  • [ 18162-48-6 ]
  • [ 180046-62-2 ]
YieldReaction ConditionsOperation in experiment
62% With 1H-imidazole; In DMF (N,N-dimethyl-formamide); at 25℃; for 16h; To a 100 mL-flask containing 79 (4.0 g, 27.8 mmol) in DMF (40 mL) was added TBDMSCl (3.56 g, 23.6 mmol) and imidazole (3.79 g, 55.6 mmol). The reaction was allowed to stir at 25 C. for 16 hours after which time saturated aqueous LiBr (50 mL) was added and the reaction extracted with ether (2×50 mL). The ether layers were pooled and extracted again with LiBr (2×35 mL). The ether layer became clear. The ether layer was then concentrated in vacuo and the product purified by flash chromatography, on a silica gel column, eluting with 1:2 ether/petroleum ether to yield 83 (3.80 g, 62%) as a homogenous oil. 1H NMR (CDCl3) delta 3.46 (d, J=6.2 Hz, 2H), 3.39 (d, J=6.2 Hz, 2H), 1.95-1.72 (m, 4H), 1.65 (m, 1H), 1.40 (m, 1H), 1.03-0.89 (m, 4H), 0.88 (s, 9H), 0.04 (s, 6H); 13C NMR (CDCl3) delta 69.2, 69.1, 41.2, 41.1, 29.5, 26.5, 18.9, -4.8; APCI m/z (rel intensity) 259 (MH+, 100).
45.1% With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 25℃; for 16h; To a 500-mL flask containing(lR,4R)-cyclohexane-l,4-diyldimethanol (80 g, 555 mmol) and 1H- imidazole (37.8 g, 555 mmol) in DMF (400 mL) was added to a solution of tert- butylchlorodimethylsilane (84 g, 555 mmol) in DMF (400 mL) at about 0C. After addition, the reaction was allowed to stir at about 25C for about 16 h. The solution was poured into ice water (200 mL) and extracted with MTBE (3x100 mL). The organics were combined, concentrated in vacuo, and purified by flash chromatography on silica gel (1 :2 EtOAc/petroleum ether) to afford the title compound (68 g, 45.1 %); lH NMR (400MHz, CDC13) delta 0.03 (s, 6 H) 0.86 - 0.96 (m, 13 H) 1.34 - 1.58 (m, 3 H) 1.81 (d, J=8.61 Hz, 4 H) 3.42 (dd, J=17.61, 6.26 Hz, 4 H)
With 1H-imidazole; In N,N-dimethyl-formamide; To a solution of trans-<strong>[3236-48-4]1,4-cyclohexanedimethanol</strong> (3.46 g, 24.0 mmol) in DMF (40 ml) was added ten?butyldimethylsilyl chloride (3.01 g, 20 mmol) and imidazole (3.27 g, 48.0 mmol). The reaction was allowed to stir overnight. The reaction was then partitioned between ether and brine. The organic layer was separated, washed with brine, dried over sodium sulfate,filtered and evaporated. The crude product was purified on a Biotage 40M silica gel column, eluting with a gradient of 10-50% ethyl acetate in hexanes to give the title compound. NMRo (ppm)(CDCl3): 3.46 (d, 2H), 3.40 (d, 2H), 1.81 (m, 4H), 1.42 (m, 2H), 1.26 (s, 1H), 0.94 (m, 4H), 0.89 (s, 9H), 0.03 (s, 6H).
  • 28
  • [ 619-82-9 ]
  • [ 3236-48-4 ]
YieldReaction ConditionsOperation in experiment
28.6% Thionyl chloride (16.6g, 139.5mmol) was added dropwise to a stirred solution of trans-cyclohexane-1,4-dicarboxylic acid (10.0g, 58.1mmol) in methanol (160mL) at 0?20°C. The resulting mixture was stirred at reflux for 4h. The resulting solution was evaporated in vacuo and the residue was partitioned between aqueous water (50mL) and dichloromethane (100mL). The organic layer was washed with aqueous NaHCO3 (40mL), brine (50mL) and dried (Na2SO4), and evaporated in vacuo to give a colorless solid (9.8g, 84.0percent). Next, a mixture of this solid (9.8g) and NaBH4 (18.5g, 488.2mmol) in THF (196mL) was stirred at reflux for 0.5h. Then methanol (69mL) was added to the resulting solution at room temperature. The resulting solution was stirred at reflux for 12h and quenched with 30percent hydrochloric acid (20mL) in and ice bath. The resulting mixture was stirred for 1h and alkalized with 50percent sodium hydroxide solution (30mL). The resultant mixture was extracted with dichloromethane (3×60mL). The combined organic extracts were dried (MgSO4) and evaporated in vacuo to give 42 (2.4g, 28.6percent) as a colorless solid. Mp: 63?65°C. 1H NMR (CDCl3): delta 0.93?1.03 (m, 4H), 1.45?1.47 (m, 2H), 1.84?1.88 (m, 4H), 3.40?3.46 (m, 4H).
  • 29
  • [ 3236-48-4 ]
  • [ 83447-96-5 ]
  • 30
  • [ 120-61-6 ]
  • [ 3236-48-4 ]
  • [ 3236-47-3 ]
  • 31
  • [ 3236-48-4 ]
  • [ 922713-02-8 ]
  • 32
  • [ 105-08-8 ]
  • [ 3236-48-4 ]
YieldReaction ConditionsOperation in experiment
72.6% With Ni/NiO-diatomite; at 200℃; for 3h;Autoclave; Inert atmosphere; 200 m of 1,4-cyclohexane dimethanol (trans isomer 67percent, cis isomer 33percent) and 200 m of the catalyst shown in the following Table 1 were introduced into a 500 ml autoclave(Comparative Example 6 is no catalyst) And the mixture was stirred at 200°C For 3 hours in a nitrogen atmosphere.
  • 33
  • [ 3236-48-4 ]
  • [ 762276-53-9 ]
  • 34
  • [ 3236-48-4 ]
  • (E)-3-Phenyl-acrylic acid 4-carbazol-9-ylmethyl-cyclohexylmethyl ester [ No CAS ]
  • 35
  • [ 3236-48-4 ]
  • 4-cyano-benzoic acid 4-carbazol-9-ylmethyl-cyclohexylmethyl ester [ No CAS ]
 

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