66634-97-7|2,4-Dimethylpent-2-enoic acid| Ambeed

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Quality Control of [ 66634-97-7 ] Purity: 97% SDS Specification

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Product Details of [ 66634-97-7 ]

CAS No. :	66634-97-7
Formula :	C₇H₁₂O₂
M.W :	128.17
SMILES Code :	CC(C)/C=C(C)/C(O)=O
MDL No. :	MFCD00209505
InChI Key :	DMHLGGQHOSTMJG-UHFFFAOYSA-N
Pubchem ID :	53422899

Safety of [ 66634-97-7 ]

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

Computational Chemistry of [ 66634-97-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	0
Fraction Csp3	0.57
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	37.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.79
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.67
Log P_o/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.	1.52
Log P_o/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	0.84
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.61
Solubility	3.18 mg/ml ; 0.0248 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.	-2.15
Solubility	0.906 mg/ml ; 0.00707 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	-0.51
Solubility	39.2 mg/ml ; 0.306 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.	-5.84 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.	0.56

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)	1.95

Application In Synthesis of [ 66634-97-7 ]

* 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 [ 66634-97-7 ]

[ 66634-97-7 ] Synthesis Path-Downstream 1~30

1
[ 25018-67-1 ]
[ 66634-97-7 ]
(1,2:4,5-di-O-isopropyliden-α-D-fructopyranose-3-yl) 2,4-dimethyl-2-pentenoate [ No CAS ]
(1,2:4,5-di-O-isopropyliden-α-D-fructopyranose-3-yl) 2,4-dimethyl-2-pentenoate [ No CAS ]

References: [1]Tetrahedron Asymmetry,2001,vol. 12,p. 1389 - 1394.

2
[ 34281-92-0 ]
[ 66634-97-7 ]
(1R,2S)-trans-2-phenyl-1-cyclohexyl 2,4-dimethyl-2-pentenoate [ No CAS ]
(1R,2S)-trans-2-phenyl-1-cyclohexyl 2,4-dimethyl-2-pentenoate [ No CAS ]

References: [1]Tetrahedron Asymmetry,2001,vol. 12,p. 1389 - 1394.

3
[ 96303-88-7 ]
[ 66634-97-7 ]
(-)-1-[(dicyclohexylsulfonamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl 2,4-dimethyl-2-pentenoate [ No CAS ]
(-)-1-[(dicyclohexylsulfonamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl 2,4-dimethyl-2-pentenoate [ No CAS ]

References: [1]Tetrahedron Asymmetry,2001,vol. 12,p. 1389 - 1394.

4
[ 599-04-2 ]
[ 66634-97-7 ]
(3R)-(-)-(4,4-dimethyl-2-oxotetrahydrofuran-3-yl) 2,4-dimethyl-2-pentenoate [ No CAS ]
(3R)-(-)-(4,4-dimethyl-2-oxotetrahydrofuran-3-yl) 2,4-dimethyl-2-pentenoate [ No CAS ]

References: [1]Tetrahedron Asymmetry,2001,vol. 12,p. 1389 - 1394.

5
[ 917-54-4 ]
[ 66634-97-7 ]
[ 3132-13-6 ]

Yield	Reaction Conditions	Operation in experiment
		Within a period of 90 min. , a solution of triethyl 2-phosphonopropionate (238 g, 1.00 mol) in dimethoxyethane (DME, 150 ml) was added dropwise with stirring under an atmosphere of N2 to a solution of NaH (43.6 g, 1.00 mol) in DME (600 ML). The mixture was then heated to reflux, and after 15 min. at reflux temp. , isobutyric aldehyde (72.1 g, 1.00 mol) was added dropwise. After a further 30 min. stirring at reflux, the mixture was poured into ice/water (1: 1,1 L). ACOH (60 ml) was added, and the product was extracted with Et2O (2x 200 ML). The combined organic extracts were washed with water (400 ML) and brine (100 ML), dried (NA2SO4), and concentrated in a rotary evaporator. The resulting residue was distilled to provide at 86-75 C/27 mbar 117 G (75 %) of 2, 4-DIMETHYLPENT-2-ENOIC acid ethyl ester. A mixture of 2, 4-DIMETHYLPENT-2-ENOIC acid ethyl ester (116 g, 742 MMOL) and KOH 85% (147 g, 2.23 mol) in water/EtOH (1: 1,2. 0 L) was REFLUXED for 1D. The ETOH was stripped off on a rotary evaporator, and the remaining mixture was washed with ET2O. The combined ethereal washings were extracted with 2 N aq. NAOH (100 ML), and all aqueous solutions were combined. Under cooling with an ice/water bath, conc. aq. H3PO4 (200 ml) was added to adjust the combined aqueous solutions to pH 3, and the product was extracted with ET20 (200 ml). The ethereal solution was washed with water (200 ml) and brine (25 ML). After drying (NA2SO4), the solvent was evaporated in a rotary evaporator to furnish 94.2 G (99%) of 2, 4-DIMETHYL-PENT-2-ENOIC acid. Under an atmosphere of N2, a 1.6 M solution of MeLi in ET20 (500 ml, 800 MMOL) was added during 105 min. dropwise with stirring between 0-10 C to a solution of 2,4- dimethylpent-2-enoic acid (41.0 g, 320 MMOL) in Et20 (1.6 L). The reaction mixture was heated to reflux for 1 h, and then between 5-15 C 5 N HCI (200 ml) was added dropwise. The organic layer was separated, the aqueous one extracted with ET20 (200 ML). The combined organic solutions were washed with water (200 mi) and brine (100 ML), dried (NA2SO4) and concentrated in a rotary evaporator to afford crude 3,5- dimethylhex-3-en-2-one, which was taken up in Et20 (160 ML). Under N2 at room temp., this solution was added dropwise with stirring to a suspension of LAH (3.34 g, 880 MMOL) in Et20 (320 ML) during 1 h. The reaction mixture was refluxed for 2 h, and then quenched between 0-5 C by addition of water (10 ml) and brine (20 ML). The organic layer was separated and the aqueous one extracted with Et20 (100 ml). The combined ethereal extracts were washed with water (100 ml) and brine (50 ml), dried (NA2SO4), and concentrated under reduced pressure. Silica-gel FC (PENTANE/ET20, 4: 1, Rf = 0.40) of the resulting residue provided 34.7 G (85% over 2 steps) of 3, 5-dimethylhex-3-en-2- ol. At 0C under N2, a 1 M solution of MEAICI2 (50 ml, 50 MMOL) in hexane was added dropwise with stirring during a period of 1 h to a solution of 3, 5-dimethylhex-3-en-2-ol (12.8 g, 100 MMOL) and isobutylene oxide (8.65 g, 120 MMOL) in cyclohexane (100 ML). The cooling bath was removed, and stirring was continued for 16 h, prior to pouring the mixture into ice/water (1: 1,100 mi). The resulting slurry was dissolved by addition of conc. aq. H3PO4, and the product extracted with Et20 (2x 100 ml). The combined organic extracts were washed with water (100 ml) and brine (25 ML), dried (NA2SO4) and concentrated in a rotary evaporator. The resulting residue was purified by silica-gel FC (PENTANE/ET2O, 19: 1, Rf = 0.12) to afford 3.10 G (15%) of 2-methyl-2-(1', 2', 4'- trimethylpent-2'-enyloxy) propan-1-ol. At 0 C under N2, N, N'-Dicyclohexylcarbodiimide (DCC, 1.03 g, 5.00 MMOL) was added to a stirred solution of 2-methyl-2-(1', 2', 4'-TRIMETHYLPENT-2'-ENYLOXY) PROPAN-1-OL (830 mg, 4.14 MMOL), acetic acid (250 mg, 4.14 MMOL) and 4- (dimethylamino) pyridine (DMAP, 50 mg, 410 MMOL) in CH2CI2 (10 ml). After stirring for 1 h at room temp. , the precipitate was vacuum filtrated and washed with CH2CI2. The combined filtrates were concentrated under reduced pressure, and the resulting residue was purified by silica- gel FC (PENTANE/ET2O, 19: 1, Rf = 0.36) to furnish 710 mg (71%) of the odouriferous title compound. IR (ATR): v = 1232/1044 CM~ (s, vC-O), 1744 cm-' (s, vO-C=O).-'H NMR (CDCI3) : No. = 0. 91/0. 92/0. 93/0. 95 (4d, J= 6.5 Hz, 6H, 4"-Me2), 1.14/1. 15 (2d, J = 6.5 Hz, 3H, 1"-Me), 1.17/1. 18 (2s, 6H, 2'-Me2), 1.60/1. 68 (2d, J= 1.5 Hz, 3H, 2"-Me), 2.07/2. 08 (2s, 3H, 2-H3), 2.48/2. 60 (2ME, 1 H, 4"-H), 3. 89/3. 90/3. 99/4.00 (4d, J = 11.0, 2H, 1'- H2), 4.01/4. 57 (2q, J = 6. 5 HZ, 1 H, 1"-H), 4. 85/5. 14 (2d, J=9. 5HZ, 1H, 3"-H).-'3C NMR (CDCI3) : 8 = 11. 1/17. 6 (2q, 2"-Me), 20. 7/20. 8 (2Q, C-2), 22. 3/22. 4/22. 6/22. 8 /23.1/23. 3 (6q, 1"-Me, 4"-ME2), 23. 4/23. 5/23. 5/23. 6 (4q, 2'-Me2), 26. 4/26. 5 (2d, C-4"), 66.0/73. 3 (2d, C-1"), 69.7/69. 8 (2T, C-1'), 74.1/74. 2 (2s, C-2'), 131. 6/131. 9 (2d, C-3"), 136.3/136. 7 (2s, C-2"), 170.7/170. 7 (2s, C-1)....

References: [1]European Journal of Organic Chemistry,2004,p. 354 - 365.
[2]Patent: WO2004/50595,2004,A1 .Location in patent: Page 7-9.

6
[ 66634-97-7 ]
(E)-2,4-dimethylpent-2-enoyl bromide [ No CAS ]

References: [1]European Journal of Organic Chemistry,2006,p. 2119 - 2133.

7
[ 66634-97-7 ]
[ 887779-55-7 ]

References: [1]European Journal of Organic Chemistry,2006,p. 2119 - 2133.

8
[ 66634-97-7 ]
[ 676532-41-5 ]