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Chemical Structure| 22535-49-5

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Product Citations

Product Citations

Shen, Zhitong ; Miyajima, Hiroki ; Fujita, Satoshi ;

Abstract: This study presents a hybrid hydrogel fiber mat system for magnetothermal actuation, designed to address the limitations of conventional temperature-dependent systems in soft robotics. The mats were fabricated via electrospinning, integrating polyurethane (PU) for mechanical flexibility, poly(N-isopropylacrylamide) (PNIPAM) for thermoresponsive behavior, and Fe3O4 nanoparticles for magnetic responsiveness. Alternating magnetic field (AMF)-induced heating of Fe3O4 nanoparticles triggers the lower critical solution temperature (LCST) phase transition of PNIPAM, enabling dynamic, reversible deformation independent of ambient temperature fluctuations. This composite structure allowed diverse deformation modes governed by fiber alignment and cutting angles, facilitating precise and tunable actuation. The demonstrations included flower-like actuation, object gripping with a fiber-based gripper, and maze navigation under magnetic guidance, showing its potential for complex, remote-controlled applications. The incorporation of Fe3O4 nanoparticles enhanced magnetic properties, enabling real-time actuation and reducing reliance on external thermal inputs. This study highlighted a stimuli-responsive material platform with broad potential applications in soft robotics, biomedical devices, and adaptive textiles, providing an innovative solution for remotely controlled and noninvasive actuation systems.

Keywords: electrospinning ; magnetic actuator ; alternative magnetic field ; hydrogel fibers ; nanoparticles

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Product Details of [ 22535-49-5 ]

CAS No. :22535-49-5
Formula : C16H12O3
M.W : 252.27
SMILES Code : C=CC(=O)OC1=CC=C(C=C1)C(=O)C1=CC=CC=C1
MDL No. :MFCD12828285
InChI Key :LTYBJDPMCPTGEE-UHFFFAOYSA-N
Pubchem ID :3015131

Safety of [ 22535-49-5 ]

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

Computational Chemistry of [ 22535-49-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 72.15
TPSA ?

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

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.63
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

3.61
Log Po/w (WLOGP)?

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

3.01
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.

2.89
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

3.68
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.16

Water Solubility

Log S (ESOL):?

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

-3.82
Solubility 0.0386 mg/ml ; 0.000153 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-4.21
Solubility 0.0156 mg/ml ; 0.0000619 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

-5.0
Solubility 0.00251 mg/ml ; 0.00000993 mol/l
Class?

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

Moderately 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

Yes
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.

-5.28 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

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)

1.92

Application In Synthesis of [ 22535-49-5 ]

* 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 [ 22535-49-5 ]

[ 22535-49-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1159136-25-0 ]
  • [ 22535-49-5 ]
YieldReaction ConditionsOperation in experiment
With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; In acetone; for 2.0h;Heating / reflux; 1.2 g (4.75 mmol) 3-chloro-propionic acid 4-benzoylphenyl ester was dissolved in 12 ml acetone. 10 mg BHT and 1 g (7.13 mmol) anhydric K2CO3 were added. The mixture was refluxed for 2 hours. A TLC analysis (Merck Kieselgel 60F254, eluent ethyl acetate/n.-hexane 30/70) indicated a complete conversion of 3-chloro-propionic acid 4-benzoylphenyl ester to 2-propenoic acid 4-benzoylphenyl ester. The inorganic salts were removed by filtration and the solvent was evaporated under reduced pressure. 0.8 g of 2-propenoic acid 4-benzoylphenyl ester was isolated. Based on TLC analysis, there were no indications for the formation of side products. This analysis was confirmed by 1H-NMR spectroscopy.
  • 2
  • [ 22535-49-5 ]
  • [ 111-42-2 ]
  • [ 947609-92-9 ]
  • 3
  • [ 814-68-6 ]
  • [ 1137-42-4 ]
  • [ 22535-49-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; water;Flow reactor; General procedure: For EX-1, the following procedure was carried out using Microreactor B, described above, with the mixing device at ambient temperature. Syringe I contained 15 g BP, 22 g TEA, and 22 g water. Syringe II contained 3 g ACL and 20 g DCM. Each syringe was placed in a separate syringe pump and the pump speeds were controlled to deliver the blends at the flow rates indicated for EX-1 in Table 3 below. The two unused addition ports of the mixing device were sealed with plugs. The molar flow ratios of BP: ACL: TEA pumped to the mixing device were 1: 1.1 :2.9. Separation of aqueous phase and an organic phase was observed in the collection vessel. Analysis of the upper, aqueous phase by NMR indicated approximately 8 mol percent of acrylic acid-TEA salt and approximately 92 mol percent TEA -HQ salt. Analysis of the lower, organic phase by NMR indicated approximately 51 mol percent 4- acryloxybenzophenone (ABP), approximately 0.01 mol percent BP and approximately 42 mol percent of the above mentioned TEA salts. Analysis of the organic layer by GC indicated 95percent Composition of ABP and 2percent of unreacted alcohol. After analysis, the organic layer was washed with water to remove salts and residual TEA. For EX-2 through EX-17, the same procedure was followed but with syringe contents and flow rates as indicated in Table 3. Blend compositions, flow rates, molar flow ratios of BP:ACL:TEA, and percent Composition are provided in Table 3.
With triethylamine; sodium hydroxide; In water; ethyl acetate; For EX-1, the following procedure was carried out using the microreactor described above, with the mixing device at ambient temperature. Container I contained 100 g BP, 50 g TEA, 20 G NaOH, and 147 g water. Container II contained 40 g ACl and 80 g EtOAc. Each container was connected to a pump and the pump speeds were controlled to deliver the mixtures in the containers at the following rates: Container I; 14 mL/min, or 0.022 mol/min of BP; Container II: 7 mL/min, or 0.028 mol/min of ACl. The two unused addition ports of the mixing device were sealed with plugs. The molar flow ratios of BP:NaOH:TEA:ACl pumped to the mixing device were approximately 1 : 1 : 1 : 1.24. Separation of aqueous phase and an organic phase was observed in the collection vessel. The organic phase was observed to have a hazy appearance. The aqueous layer was removed from the collection vessel. Results of analysis of the organic layer by GC and NMR are presented in Table 1.
  • 4
  • [ 1137-42-4 ]
  • [ 920-46-7 ]
  • [ 22535-49-5 ]
YieldReaction ConditionsOperation in experiment
In water; butanone; Synthesis of 4-acryloyloxy-benzophenone 1.3 g (16.25 mmoli) of NaOH 50percent water solution, were added to a solution of 3 g (15.21 mmol) of 4-hydroxybenzophenone in 20 cc of methyl ethyl ketone. After 30 minutes under stirring, a solution of 1.59 g (15.21 mmol) of methacryloyl chloride in 5 mL of methyl ethyl ketone were added dropwise. After the addition the reaction mixture was stirred for 1 hour, filtered and the solvent was evaporated. The oil residue was purified by flash chromatography on silica gel (eluent CH2Cl2) to obtain 2.74 g of a colourless liquid. 1HNMR (CDCl3): delta (ppm): 2.10 (s, 3H); 5.82 (s, 1H); 6.40 (s, 1H); 7.2-7.3 (m, 2H); 7.45-7.55 (m, 2H); 7.60-7.65 (m, 1H); 7.75-7.85 (m, 2H); 7.85-7.95 (m, 2H)
  • 5
  • [ 625-36-5 ]
  • [ 1137-42-4 ]
  • [ 22535-49-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; water;Flow reactor; General procedure: EX-22 was carried out using Microreactor B. For EX-22, syringe I contained 15 g BP, 33 g TEA, and 33 g water. Syringe II contained 4.2 g 3CPC and 20 g DCM. Each syringe was placed in a separate syringe pump and the pump speeds were controlled to deliver the blends at the flow rates indicated for EX-22 in Table 8 below. The two unused addition ports of the mixing device were sealed with plugs. Separation of aqueous phase and an organic phase was observed in the collection vessel. Analysis of the upper, aqueous phase by NMR indicated approximately 8 mol percent of acrylic acid-TEA salt and approximately 92 mol percent TEA-HC1 salt. Analysis of the lower, organic phase by NMR indicated approximately 51 mol percent ABP, approximately 0.01 mol percent BP and approximately 42 mol percent of the above mentioned TEA salts. Analysis by GC indicated the organic layer was 98percent ABP and 2percent unreacted alcohol. After analysis, the organic layer was washed with water to remove salts and residual TEA. For EX-23 through EX-26, the same procedure was followed as described for EX-22, except that flow rates were as indicated in Table 8. Blend compositions, flow rates, and percent Composition are provided in Table 8.
  • 6
  • [ 22535-49-5 ]
  • [ 108-95-2 ]
  • 4-benzoylphenyl (E)-3-(2-hydroxyphenyl)acrylate [ No CAS ]
 

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