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Chemical Structure| 1445-91-6 Chemical Structure| 1445-91-6

Structure of (S)-(-)-Phenylethanol
CAS No.: 1445-91-6

Chemical Structure| 1445-91-6

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Synonyms: (S)-(-)-1-Phenylethanol; (S)-1-Phenylethanol

4.5 *For Research Use Only !

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Product Citations

Product Citations

Mills, Mitchell ;

Abstract: The development of novel deuterated and fluorinated bioisosteres has significantly impacted the pharmaceutical and agricultural industry and created a growing demand for new synthetic methodology. Both deuterated and fluorinated small molecules exist at the forefront of drug discovery due to their unique ability to attenuate the pharmacokinetic properties of new and currently existing drugs. Selective, highthroughput methods for deuteration and fluorination are scarce in the literature, especially methods that introduce D or F atoms asymmetrically. Benzylic C−H bonds are oftentimes key sites for enzymatic manipulation in metabolic processes, alteration of C−H bonds to C−D or C−F bonds at the benzylic site of organic molecules affects the metabolic process, making this a key site for bioisosterism. Using state-of-the-art methods to synthesize chiral by virtue of deuterium small molecules requires significant synthetic overhead with limited methods for chiral analysis due to the similar nature of H and D. Asymmetric fluorination has been restricted to α,β-unsaturated carbonyl compounds that can transform into metal enolates, and only two literature examples of enantioselective fluorinations of aryl alkenes. Herein, enantioselective methods for both deuteration and fluorination are described. Regio- and enantioselective hydrodeuteration of the π-bond of aryl alkenes was successfully achieved using a chiral Cu−H catalyst with a protic D-source. Molecular rotational resonance (MRR) spectroscopy was utilized as a novel analytical method for determining %ee, absolute stereochemistry, and identifying isotopomers and isotopologues. This substrate scope includes various aromatic and heteroaromatic alkenes with excellent yields and high enantioselectivities. By substituting the protic D-source for Selectfluor, an electrophilic fluorinating reagent, enantioselective fluorination was also achieved. Optimization of the catalytic conditions will reveal the feasibility of achieving high enantioselectivities and yields. In this work, my contributions to both the deuteration and fluorination projects is described.

Purchased from AmBeed: 1445-91-6

Alternative Products

Product Details of [ 1445-91-6 ]

CAS No. :1445-91-6
Formula : C8H10O
M.W : 122.16
SMILES Code : C[C@H](O)C1=CC=CC=C1
Synonyms :
(S)-(-)-1-Phenylethanol; (S)-1-Phenylethanol
MDL No. :MFCD00064264
InChI Key :WAPNOHKVXSQRPX-ZETCQYMHSA-N
Pubchem ID :443135

Safety of [ 1445-91-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H311-H315-H318
Precautionary Statements:P501-P264-P280-P361+P364-P332+P313-P302+P352+P312-P305+P351+P338+P310-P405
Class:8(6.1)
UN#:2922
Packing Group:

Computational Chemistry of [ 1445-91-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 37.38
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.91
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

1.42
Log Po/w (WLOGP)?

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

1.42
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.

1.87
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

1.86
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.7

Water Solubility

Log S (ESOL):?

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

-1.92
Solubility 1.47 mg/ml ; 0.012 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.

-1.45
Solubility 4.34 mg/ml ; 0.0355 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

-2.21
Solubility 0.752 mg/ml ; 0.00615 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

Yes
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.

-6.04 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

2.0
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)

1.0

Application In Synthesis of [ 1445-91-6 ]

* 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 [ 1445-91-6 ]

[ 1445-91-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 93222-42-5 ]
  • [ 98-86-2 ]
  • [ 1445-91-6 ]
  • [ 1517-69-7 ]
  • 2
  • [ 434-45-7 ]
  • [ 1445-91-6 ]
  • [ 10531-50-7 ]
  • [ 340-06-7 ]
  • [ 146801-19-6 ]
  • 3
  • [ 1445-91-6 ]
  • [ 151-10-0 ]
  • [ 85-27-8 ]
  • [ 106552-08-3 ]
  • 4
  • [ 1445-91-6 ]
  • [ 56844-12-3 ]
  • (S)-6-bromo-4-(1-phenylethoxy)thieno[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With caesium carbonate; In acetonitrile; for 24h;Inert atmosphere; Reflux; General procedure: 6-Bromo-4-chlorothieno[2,3-d]pyrimidine(5a) (200 mg, 0.802 mmol) was mixed with 1-phenylethanol (2a) (118 mg, 0.962 mmol), Cs2CO3( 313 mg, 0.962 mmol) and acetonitrile (2 mL). The reaction was then stirredunder nitrogen atmosphere at reflux and followed by GC. The mixture was cooledto rt, diluted with EtOAc (40 mL), washed with sat. aq. KHCO3 (20mL), water (2×20 mL) and brine (30 mL). The combined organic fractions weredried over Na2SO4 and concentrated in vacuum. Crudeproduct was absorbed onto Celite 545 and purified by silica gel columnchromatography (n-pentane/EtOAc,6/1). This gave 245 mg (0.730 mmol, 91%) of 6a as an off-white solid.
  • 5
  • [ 55589-47-4 ]
  • [ 1445-91-6 ]
  • [ 54010-75-2 ]
  • [ 1539-42-0 ]
  • [ 75-05-8 ]
  • C29H31N5OZn(2+) [ No CAS ]
 

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Technical Information

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