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Chemical Structure| 2136-75-6 Chemical Structure| 2136-75-6

Structure of 2136-75-6

Chemical Structure| 2136-75-6

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Product Details of [ 2136-75-6 ]

CAS No. :2136-75-6
Formula : C20H17OP
M.W : 304.32
SMILES Code : C1=CC=C(C=C1)P(=CC=O)(C2=CC=CC=C2)C3=CC=CC=C3
MDL No. :MFCD00006994
InChI Key :CQCAYWAIRTVXIY-UHFFFAOYSA-N
Pubchem ID :75051

Safety of [ 2136-75-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P302+P352-P305+P351+P338

Computational Chemistry of [ 2136-75-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 22
Num. arom. heavy atoms 18
Fraction Csp3 0.0
Num. rotatable bonds 4
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 97.28
TPSA ?

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

26.88 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

3.59
Log Po/w (WLOGP)?

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

2.98
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.

4.41
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

5.44
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.28

Water Solubility

Log S (ESOL):?

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

-4.33
Solubility 0.0142 mg/ml ; 0.0000468 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.

-3.84
Solubility 0.0439 mg/ml ; 0.000144 mol/l
Class?

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

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

-7.53
Solubility 0.00000909 mg/ml ; 0.0000000299 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

2.0 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)

4.09

Application In Synthesis of [ 2136-75-6 ]

* 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 [ 2136-75-6 ]

[ 2136-75-6 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 7310-97-6 ]
  • [ 2136-75-6 ]
  • [ 142397-45-3 ]
  • 2
  • [ 118289-17-1 ]
  • [ 2136-75-6 ]
  • 3-[4-(2-bromopyridinyl)]-2-propenal [ No CAS ]
  • 3
  • [ 2136-75-6 ]
  • [ 109466-87-7 ]
  • (E)-3-[2-nitro-4-(trifluoromethyl)phenyl]acrylaldehyde [ No CAS ]
  • 4
  • [ 2136-75-6 ]
  • [ 21204-67-1 ]
  • [ 13937-08-1 ]
  • methyl (triphenylphosphoranylidine) acetate [ No CAS ]
  • 5
  • [ 2136-75-6 ]
  • [ 1439-36-7 ]
  • [ 13937-08-1 ]
  • [ 66085-96-9 ]
  • 6
  • [ 16583-06-5 ]
  • [ 2136-75-6 ]
  • (E)-2,3,4,5-tetrafluorocinnamaldehyde [ No CAS ]
  • (E,E)-5-(2,3,4,5-tetrafluorophenyl)penta-2,4-dienal [ No CAS ]
  • 7
  • [ 62254-74-4 ]
  • [ 2136-75-6 ]
  • C7H7NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 25℃; General procedure: The reaction mixture of aldehyde (0.5mmol) and 2-(triphenylphosphoranylidene)acetaldehyde (0.51mmol) in DMF (0.5mL) was stirred for 1-4 days and detected with TLC. The reaction mixture was extracted with dichloromethane (10mL×3). The combined organic extracts were rinsed with brine (5mL×3) and dried over anhydrous magnesium sulfate, and the volatile components were evaporated under vacuum to give the crude product, which was subjected to the PTLC purification using hexanes/ethyl acetate (1/1, v/v) as eluent to give the respective product. All intermediates were directly used for the next step reaction after confirming with their 1H NMR data. The 1H NMR data for the sixteen known (E)-3-aryl-2-propenals (33, 34, 36, 37, 39-46, 48, 49, 56, 57) are in consistent with those reported in the literature.
  • 8
  • [ 3012-80-4 ]
  • [ 2136-75-6 ]
  • [ 545424-53-1 ]
YieldReaction ConditionsOperation in experiment
46% In N,N-dimethyl-formamide; at 25℃; General procedure: The reaction mixture of aldehyde (0.5mmol) and 2-(triphenylphosphoranylidene)acetaldehyde (0.51mmol) in DMF (0.5mL) was stirred for 1-4days and detected with TLC. The reaction mixture was extracted with dichloromethane (10mL×3). The combined organic extracts were rinsed with brine (5mL×3) and dried over anhydrous magnesium sulfate, and the volatile components were evaporated under vacuum to give the crude product, which was subjected to the PTLC purification using hexanes/ethyl acetate (1/1, v/v) as eluent to give the respective product. All intermediates were directly used for the next step reaction after confirming with their 1H NMR data. The 1H NMR data for the sixteen known (E)-3-aryl-2-propenals (33, 34, 36, 37, 39-46, 48, 49, 56, 57) are in consistent with those reported in the literature.
  • 9
  • [ 19955-99-8 ]
  • [ 2136-75-6 ]
  • 3-(3-vinylphenyl)acrolein [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In toluene; for 17h;Reflux; Into a 1L dry single-mouth flask, add <strong>[19955-99-8]3-vinylbenzaldehyde</strong> (13.2g, 0.10 mol), (formylmethylene)triphenylphosphine (33.5g, 0.11mmol) and toluene (200 ml). Reflux the reaction system for 17 hours then concentrated. The crude product is purified by column chromatography (eluant: petroleum ether/ethyl acetate of the volume ratio: 100/1 to 80/20) to obtain a yellow solid (9.6g, yield: 60%)
  • 10
  • [ 5779-93-1 ]
  • [ 2136-75-6 ]
  • (E)-3-(2,3-dimethylphenyl)acrylaldehyde [ No CAS ]
  • 11
  • [ 18362-30-6 ]
  • [ 2136-75-6 ]
  • (E)-3-(2-chloro-6-hydroxyphenyl)acrylaldehyde [ No CAS ]
  • 12
  • [ 2136-75-6 ]
  • [ 148625-35-8 ]
  • C11H9NO5 [ No CAS ]
  • 13
  • [ 2136-75-6 ]
  • [ 109466-87-7 ]
  • C10H6F3NO3 [ No CAS ]
  • 14
  • [ 89-98-5 ]
  • [ 2136-75-6 ]
  • [ 1794-45-2 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; A suspension of 2-chlorobenzaldehyde (200 mg, 1.428 mmol) in dichloromethane was degassed with ISh for 15 minutes at room temperature, following which 2-(triphenyl- 5- phosphanylidene)acetaldehyde (433 mg, 1.428 mmol) was added and the resulting reaction mixture stirred overnight. The crude reaction mixture was concentrated in vacuo and passed through a silica plug using 2% ethyl acetate in hexane as an eluent.
  • 15
  • [ 61018-49-3 ]
  • [ 2136-75-6 ]
  • (E)-3-(5-methyl-1,3,4-thiadiazol-2-yl)prop-2-enal [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 20℃; for 24h; 5-Methyl-1,3,4-thiadiazole-2-carbaldehyde (700 g) was dissolved in ACN (10 ml) and (formylmethylene)triphenylphosphorane (1.8 g) was added with stirring. After stirring for 24 h at RT the solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25 g; 0 % to 100 % EA in heptane in 8 min). The compound containing fractions were combined and the solvent was removed in vacuo to yield 293 mg of the title compound containing some residual triphenylphosphine oxide (13 %). LC/MS: m/z = 155.1 [M+H]+; tR: 0.52 min (LC/MS-method D). 1H N MR (600 MHz, DMSO-d6) δ ppm 9.77 (1 H), 8.05 (1 H), 6.92 (1 H), 2.80 (3 H).
In acetonitrile; at 20℃; for 24h; 5-Methyl-1,3,4-thiadiazole-2-carbaldehyde (700 g) was dissolved in ACN (10 ml) and (formylmethylene)triphenylphosphorane (1.8 g) was added with stirring. After stirring for 24 h at RT the solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25 g; 0 % to 100 % EA in heptane in 8 min). The compound containing fractions were combined and the solvent was removed in vacuo to yield 293 mg of the title compound containing some residual triphenylphosphine oxide (13 %). LC/MS: m/z = 155.1 [M+H]+; tR: 0.52 min (LC/MS-method D). 1H N MR (600 MHz, DMSO-d6) δ ppm 9.77 (1 H), 8.05 (1 H), 6.92 (1 H), 2.80 (3 H).
 

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