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Chemical Structure| 2605-68-7 Chemical Structure| 2605-68-7

Structure of 2605-68-7

Chemical Structure| 2605-68-7

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Product Details of [ 2605-68-7 ]

CAS No. :2605-68-7
Formula : C22H21O2P
M.W : 348.38
SMILES Code : COC(=O)C(C)=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1
MDL No. :MFCD08062441
InChI Key :WCXPAYJKBTVUBC-UHFFFAOYSA-N
Pubchem ID :10569721

Safety of [ 2605-68-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 2605-68-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 25
Num. arom. heavy atoms 18
Fraction Csp3 0.09
Num. rotatable bonds 5
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 107.97
TPSA ?

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

36.11 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

3.96
Log Po/w (WLOGP)?

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

3.35
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.

4.73
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

5.42
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.49

Water Solubility

Log S (ESOL):?

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

-4.7
Solubility 0.00699 mg/ml ; 0.0000201 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-4.42
Solubility 0.0133 mg/ml ; 0.0000381 mol/l
Class?

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

Moderately 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

-8.02
Solubility 0.00000337 mg/ml ; 0.0000000097 mol/l
Class?

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

Poorly 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.

-5.61 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

1.0
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

0.0
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

1.0 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)

3.97

Application In Synthesis of [ 2605-68-7 ]

* 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 [ 2605-68-7 ]

[ 2605-68-7 ] Synthesis Path-Downstream   1~35

  • 4
  • [ 5445-17-0 ]
  • [ 603-35-0 ]
  • [ 2605-68-7 ]
YieldReaction ConditionsOperation in experiment
97% A mixture of methyl-2-bromopropionate (S7) (2.00 mL, 17.9 mmol, 1.10 eq) and triphenylphosphine (4.27 g,16.3 mmol, 1.00 eq) in water (18.0 mL) was stirred at 70 C for 2.5 h. Both the aqueousand the organic layer still contained PPh3. The temperature was raised to 80 C and themixture was stirred for further 2 h. According to TLC, there was still a considerableamount of PPh3. Therefore, the mixture was stirred at 75 C overnight. After totally 23 hthe mixture was allowed to cool to rt. Afterwards aqueous NaOH (38 mL 1 M, 2.3 eq) wasadded, which led to the immediate precipitation of a yellow solid. The suspension wasstirred for 5 min, then CH2Cl2 (50 mL) was added and the layers were separated. Theaqueous phase was extracted with CH2Cl2 (2×50 mL), washed with brine, dried overMgSO4 and concentrated under reduced pressure. The crude was obtained as a yellow oil,which turned into a solid upon addition of pentane. The solid was washed with hexane(3×20 mL) and dried in vacuo to afford phosphonium ylide 17 (5.48 g, 97%) as a slightlyyellow powder.
91% With potassium iodide; In water; toluene; at 70℃; for 20h; After dissolving 5 g (19.06 mmol) of triphenylphosphine in 15 ml of toluene, an aqueous solution of 0.32 g (1.90 mmol) of potassium iodide in 15 ml of distilled water and 3.2 ml (28.6 mmol) of methyl 2-bromopropionate were added thereto. And the mixture was stirred at 70 C for 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, basified (pH 9) with 10 N aqueous sodium hydroxide solution, and extracted with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, filtered under reduced pressure, and distilled under reduced pressure. The obtained solid was washed with hexane and then filtered under reduced pressure and dried under reduced pressure to give 6.0 g (yield: 91%) of the title compound.
  • 5
  • [ 2689-62-5 ]
  • [ 2605-68-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In dichloromethane; water; at 20℃; for 0.25h;Inert atmosphere; Sodium hydroxideaq. (2 M, 85 mL, 170mmol) was added to a solution ofcarbomethoxy methyl triphenylphosphonium bromide (5.15 g,12.0mmol) and CH2Cl2 (20 mL) at room temperature. Afterstirring for 15min at room temperature, the solution wasextracted with CHCl3 (2 15 mL), washed with brine (15 mL),dried over Na2SO4 and concentrated. The resulting ylide wasused without further purification. A solution of the ylide and CH2Cl2 (30 mL) was added to asolution of lactol 36 (1.00 g, 5.98mmol) and CH2Cl2 (30 mL) atroom temperature. After maintaining for 19 h at room temperature,diisopropylethylamine (5.2 mL, 30mmol) and BOMCl(3.3 mL, 24mmol) were added to the yellow solution at roomtemperature. The solution was maintained for 2 d at roomtemperature, quenched with H2O (40 mL) and extracted withCHCl3 (3 30 mL). The combined organic extracts werewashed with brine (30 mL), dried over Na2SO4 and concentrated.The residue was purified by silica gel column chromatography(EtOAc/hexane 1:24 to 1:7) to give 2.27 g of a mixtureof the unsaturated methylester 37 and benzyl alcohol, whichwas used in the next step without further purification. Foran analytical sample, the mixture was purified by HPLC(PEGASIL Silica 1205250 20 mm, UV 254 nm, EtOAc/hexane 1:3, 10mL/min, TR = 12min) to afford the pureunsaturated methylester 37
  • 7
  • [ 375-00-8 ]
  • [ 2605-68-7 ]
  • methyl 3-<(triphenylphosphoranylidene)amino>-3-heptafluoropropylmethacrylate [ No CAS ]
  • 8
  • [ 56882-05-4 ]
  • [ 2605-68-7 ]
  • [ 112219-60-0 ]
  • 9
  • [ 123219-41-0 ]
  • [ 2605-68-7 ]
  • [ 131589-25-8 ]
  • 12
  • [ 132047-80-4 ]
  • [ 2605-68-7 ]
  • [ 100818-81-3 ]
  • 13
  • [ 132047-98-4 ]
  • [ 2605-68-7 ]
  • [ 132047-99-5 ]
  • 14
  • (1S,4R,6R,7R)-7-Methoxymethoxy-1,4,6-trimethyl-2,5-dioxa-bicyclo[2.2.1]heptan-3-ol [ No CAS ]
  • [ 2605-68-7 ]
  • [ 111904-97-3 ]
  • [ 111904-96-2 ]
  • 15
  • [ 132463-65-1 ]
  • [ 2605-68-7 ]
  • [ 132463-74-2 ]
  • 16
  • 2,5-anhydro-3-O-(tert-butyldimethylsilyl)-6-deoxy-2,4-di-C-methyl-D-gulofuranose [ No CAS ]
  • [ 2605-68-7 ]
  • [ 111905-12-5 ]
  • [ 111905-11-4 ]
  • 17
  • [ 146518-09-4 ]
  • [ 2605-68-7 ]
  • (Z)-(4R,5S,6S,7S)-7-Benzyloxy-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2,4,6-trimethyl-hept-2-enoic acid methyl ester [ No CAS ]
  • [ 120040-79-1 ]
  • 18
  • [ 101032-48-8 ]
  • [ 2605-68-7 ]
  • [ 105859-21-0 ]
  • 19
  • (2RS,4RS,6E)-2,4-dimethyl-5-(benzyloxy)-6,8-nonadienal [ No CAS ]
  • [ 2605-68-7 ]
  • (2E,4RS,6RS,8E)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienoate [ No CAS ]
  • 20
  • [ 2605-68-7 ]
  • [ 15186-48-8 ]
  • [ 122520-52-9 ]
  • (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-2-propenoate [ No CAS ]
  • 22
  • [ 2605-68-7 ]
  • C22H32O [ No CAS ]
  • cerorubenic acid-III methyl ester [ No CAS ]
  • 25
  • [ 21422-02-6 ]
  • [ 2605-68-7 ]
  • [ 84384-84-9 ]
  • 26
  • [ 6628-86-0 ]
  • [ 2605-68-7 ]
  • [ 307335-62-2 ]
  • 27
  • [ 32268-30-7 ]
  • [ 2605-68-7 ]
  • [ 84384-85-0 ]
  • 28
  • [ 2605-68-7 ]
  • 4,6-dihydroxy-2-methoxy-3-(3-methyl-but-2-enyl)-benzaldehyde [ No CAS ]
  • 5-methoxy-3,8,8-trimethyl-8<i>H</i>-pyrano[3,2-<i>g</i>]chromen-2-one [ No CAS ]
  • 29
  • [ 2605-68-7 ]
  • [ 22323-80-4 ]
  • [ 122520-69-8 ]
  • 30
  • [ 6068-62-8 ]
  • [ 2605-68-7 ]
  • [ 84695-32-9 ]
  • 32
  • [ 2605-68-7 ]
  • [ 107-02-8 ]
  • [ 122057-55-0 ]
YieldReaction ConditionsOperation in experiment
70% In dichloromethane; at 47℃; for 3h; To a solution of the phosphonium ylide17 (62.1 g, 178 mmol, 1.00 eq) in CH2Cl2 (230 mL) was added acrolein (18) (11.9 mL,178 mmol, 1.00 eq) dropwise at rt. The addition was ceased from time to time due toexcessive boiling of the mixture. After the addition, the yellow solution was heated (47 Coil bath) to maintain a gentle reflux. After 3 h, the mixture was allowed to cool to rt andstored overnight. Then it was concentrated under reduced pressure (Vigreux, short pathdistillation, “Hausvakuum”, 55 C oil bath), which took several hours. The concentrate wasthen cooled to 0 C, pentane was added, the resulting suspension was filtered and the filtercake was washed with pentane. The combined filtrates were concentrated (Vigreux, shortpath distillation, 50 C oil bath) and the crude was purified by distillation (75-77 oil bath, 20 mbar, bp = 59-60 C) to afford 19 as a colourless liquid (70%).1H-NMR (CDCl3, 400.1 MHz): δ = 7.17 (mc, 1H), 6.66 (ddd, J = 10.1 Hz, J = 11.3 Hz, J = 16.8 Hz, 1H), 5.56 (mc, 1H), 5.45 (mc, 1H), 3.77 (s, 3H), 1.96 (mc, 3H).
  • 33
  • [ 882165-71-1 ]
  • [ 2605-68-7 ]
  • [ 882165-72-2 ]
  • 34
  • [ 882165-58-4 ]
  • [ 2605-68-7 ]
  • [ 882165-81-3 ]
  • 35
  • [ 882165-90-4 ]
  • [ 2605-68-7 ]
  • [ 882165-91-5 ]
 

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