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[ CAS No. 1929-29-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1929-29-9
Chemical Structure| 1929-29-9
Chemical Structure| 1929-29-9
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Product Details of [ 1929-29-9 ]

CAS No. :1929-29-9 MDL No. :MFCD00002777
Formula : C10H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :FIUFLISGGHNPSM-UHFFFAOYSA-N
M.W : 180.20 Pubchem ID :95750
Synonyms :

Calculated chemistry of [ 1929-29-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.29
TPSA : 46.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 1.71
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 1.91
Consensus Log Po/w : 1.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.23
Solubility : 1.06 mg/ml ; 0.00586 mol/l
Class : Soluble
Log S (Ali) : -2.5
Solubility : 0.57 mg/ml ; 0.00316 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.354 mg/ml ; 0.00196 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 1929-29-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1929-29-9 ]

* 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.

  • Upstream synthesis route of [ 1929-29-9 ]
  • Downstream synthetic route of [ 1929-29-9 ]

[ 1929-29-9 ] Synthesis Path-Upstream   1~55

  • 1
  • [ 1929-29-9 ]
  • [ 13623-25-1 ]
YieldReaction ConditionsOperation in experiment
100% With trifluorormethanesulfonic acid In dichloromethane at 0 - 80℃; for 1 h; High pressure; Inert atmosphere; Green chemistry General procedure: Trifluoromethane sulfonic acid (3 eq.) was gently added to a cooled (0 °C) solution of a 3-Phenylpropionic acid (0.5 mmol) in dry CH2Cl2 (1.0 mL) in a 12 mL Q-tube™ pressure tube, furnished by QLabtech. The temperature was raised to room temperature. A Teflon septum was placed on the top of the tube and the appropriate cap and pressure adapter were used. The mixture was heated in an oil bath at 80 °C. The reaction was monitored by TLC and GC/MS until the reactant disappeared. The mixture was poured into ice and extracted three times with CH2Cl2. The organic phase collected was dried on Na2SO4, filtered and concentrated under vacuum. The desired pure product was separated from the crude by flash chromatography.
88% With thionyl chloride In dichloromethane (a)
To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0.279 mol) in 500 ml of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 ml (0.418 mol) of thionyl chloride, the mixture was stirred 10 h, at room temperature and the solvent was removed in vacuo.
The residue was dissolved in 1000 ml of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was sitrred at room temperature for 1 h.
The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2*200 ml).
The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88percent) of 6-methoxy-1-indanone.
88% With thionyl chloride In dichloromethane (a)
To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0,279 mol) in 500 mL of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 mL (0.418 mol) of thionyl chloride, the mixture was stirred 10 h at room temperature and the solvent was removed in vacuo.
The residue was dissolved in 1000 mL of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was stirred at room temperature for 1 h.
The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2*200 mL).
The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88percent) of 6-methoxy-1-indanone.
Reference: [1] Molecules, 2014, vol. 19, # 5, p. 5599 - 5610
[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 5, p. 470 - 475
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
[4] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[5] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1741 - 1745
[6] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
[7] Journal of the American Chemical Society, 1945, vol. 67, p. 1853
[8] Journal of the American Chemical Society, 1949, vol. 71, p. 1092,1095
[9] Yakugaku Zasshi, 1956, vol. 76, p. 163,165, 166[10] Chem.Abstr., 1956, p. 13850
[11] Angewandte Chemie, 1954, vol. 66, p. 435
[12] Monatshefte fuer Chemie, 1978, vol. 109, p. 405 - 419
[13] Chemische Berichte, 1969, vol. 102, p. 3656 - 3665
[14] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 4, p. 687 - 695
[15] Heterocycles, 1988, vol. 27, # 9, p. 2213 - 2217
[16] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 407 - 412
[17] Patent: US5569655, 1996, A,
[18] European Journal of Medicinal Chemistry, 2010, vol. 45, # 1, p. 25 - 37
[19] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[20] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5788 - 5793
[21] Patent: US5554620, 1996, A,
  • 2
  • [ 1929-29-9 ]
  • [ 13623-25-1 ]
  • [ 146301-02-2 ]
  • [ 13577-08-7 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
[2] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
[3] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
  • 3
  • [ 1929-29-9 ]
  • [ 62803-47-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 4, p. 687 - 695
[2] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
[3] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
  • 4
  • [ 830-09-1 ]
  • [ 1929-29-9 ]
YieldReaction ConditionsOperation in experiment
95.2% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; for 5 h; To a solution of 3-(4-methoxyphenyl)acrylic acid (15, 14.7 mmol) in THF (50 mL) was added a catalytic amount of 10percent palladium on activated carbon to carry out hydrogenation, followed by stirring for 5 h at room temperature. The mixture was filtered, and the filtrate was concentrated in vacuo to give a white solid with a yield of 95.2percent, mp 102-103 °C
95.2% With palladium 10% on activated carbon In tetrahydrofuran; methanol at 20℃; for 5 h; Plus p-methoxycinnamic acid(11a, 14.7 mmol), tetrahydrofuran (50 mL),Methanol (20 mL),Catalytic amount of 10percent Pd / C, hydrogen, The reaction was stirred at room temperature for 5 h. The reaction was terminated and the solid was filtered off. The solution was concentrated to dryness under reduced pressure to give a white solid, 95.2percent yield,
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 10, p. 3192 - 3203
[2] Pharmazie, 2010, vol. 65, # 12, p. 913 - 918
[3] Patent: CN106146450, 2016, A, . Location in patent: Paragraph 0162; 0163; 0164
[4] Canadian Journal of Chemistry, 2012, vol. 90, # 9, p. 758 - 761
[5] Synthetic Communications, 2012, vol. 42, # 6, p. 893 - 904
[6] Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 5, p. 1173 - 1187
[7] Journal of the Chemical Society, 1877, vol. 31, p. 409[8] Journal of the Chemical Society, 1878, vol. 33, p. 215
[9] Journal of the Chemical Society, 1929, p. 1448
[10] Journal fuer Praktische Chemie (Leipzig), 1982, vol. 324, # 3, p. 491 - 497
[11] Chemical Communications, 2004, # 8, p. 930 - 931
[12] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[13] Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1853 - 1860
  • 5
  • [ 15823-04-8 ]
  • [ 1929-29-9 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Chemische Berichte, 1874, vol. 7, p. 1736[3] Gazzetta Chimica Italiana, 1875, vol. 5, p. 6
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1900, vol. 131, p. 43[5] Annales de Chimie (Cachan, France), 1902, vol. <7> 25, p. 507,537
[6] Journal of Organic Chemistry, 2000, vol. 65, # 13, p. 4179 - 4184
[7] Tetrahedron, 2010, vol. 66, # 14, p. 2633 - 2641
  • 6
  • [ 943-89-5 ]
  • [ 1929-29-9 ]
YieldReaction ConditionsOperation in experiment
86.1% With hydrogenchloride; zinc amalgam In tetrahydrofuran; water General procedure: A mixture of zinc powder (25 g, 0.384 mol) and mercuric chloride(3.1 g, 0.0114 mol) was suspended in 100 mL of water in a 250 mLbeaker. The mixture was treated with 50 mL of con. HCl slowly dropwise and after completion of addition, the stirring was continued for15 min. The mixture was decanted to separate the solution and theremaining Zn-Hg amalgam was used for reduction. To a mixture of substituted cinnamic acid (1a-e, 0.134 mol), THF(150 mL) and 5 N HCl (100 mL) was added above freshly prepared Zn-Hg amalgam slowly portion wise. An additional 5 N HCl (50 mL) addedand the stirring continued for 2 h. After completion of reaction, asmonitored by TLC hexane/ethyl acetate (8:2), the reaction mixture waspoured into water (200 mL) and extracted with chloroform(2×400 mL), The organic layer was washed with brine solution, driedover Na2SO4 and concentrated. The crude residue was subjected to column chromatography on silica gel using hexane/ethyl acetate mixturesas eluents. The fractions were monitored using TLC and purecompound was obtained from the fractions eluted with ethyl acetate inhexane, 5percent/95percent (v/v). These fractions were combined and concentratedto obtained 3-(substituted-phenyl)-propionic acids (2a-e) asoily compounds with yields of 79–86percent.
Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Tetrahedron Letters, 2008, vol. 49, # 42, p. 6137 - 6140
[3] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
[4] Bioorganic Chemistry, 2018, vol. 80, p. 408 - 421
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 30, p. 7785 - 7788[6] Angew. Chem., 2014, vol. 53, # 30, p. 7919 - 7922,4
[7] Chemistry Letters, 2003, vol. 32, # 12, p. 1186 - 1187
[8] Phytochemistry (Elsevier), 1992, vol. 31, # 4, p. 1179 - 1184
[9] Journal of the Indian Chemical Society, 1988, vol. 65, # 3, p. 187 - 191
[10] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 14, p. 1519 - 1522
[11] Journal of Organic Chemistry, 2004, vol. 69, # 25, p. 8975 - 8978
[12] Tetrahedron Letters, 2005, vol. 46, # 37, p. 6203 - 6204
[13] Journal of Medicinal Chemistry, 2006, vol. 49, # 4, p. 1494 - 1498
[14] Journal of the American Chemical Society, 2002, vol. 124, # 17, p. 4540 - 4541
[15] Patent: US4987132, 1991, A,
[16] Synthetic Communications, 2008, vol. 38, # 10, p. 1601 - 1609
[17] Russian Chemical Bulletin, 2011, vol. 60, # 1, p. 63 - 68
  • 7
  • [ 201230-82-2 ]
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Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 15, p. 1769 - 1770
  • 8
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Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 16, p. 2544 - 2550
  • 9
  • [ 24680-50-0 ]
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Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5645 - 5647
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 2, p. 433 - 445
  • 10
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Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 8, p. 2257 - 2260
  • 11
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Reference: [1] Tetrahedron, 2004, vol. 60, # 50, p. 11533 - 11540
  • 12
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Reference: [1] Heterocycles, 2004, vol. 63, # 12, p. 2797 - 2803
[2] Catalysis Today, 2012, vol. 198, # 1, p. 154 - 173
  • 13
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Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 5, p. 1190 - 1193
  • 14
  • [ 59363-22-3 ]
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 10, p. 2616 - 2620[2] Angew. Chem., 2018, vol. 130, p. 2646 - 2650,5
  • 15
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Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 17, p. 4739 - 4741
  • 16
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Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 17, p. 4739 - 4741
  • 17
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  • 18
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Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
  • 19
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  • [ 1929-29-9 ]
Reference: [1] Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 585 - 596
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1900, vol. 131, p. 43[3] Annales de Chimie (Cachan, France), 1902, vol. <7> 25, p. 507,537
  • 20
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Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[3] Journal of the Chemical Society, 1877, vol. 31, p. 409[4] Journal of the Chemical Society, 1878, vol. 33, p. 215
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 10, p. 3192 - 3203
[6] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[7] Chemistry Letters, 2013, vol. 42, # 9, p. 1051 - 1052
[8] Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1853 - 1860
[9] Patent: CN106146450, 2016, A,
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  • 22
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  • 23
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  • 24
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  • 25
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  • 26
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[2] Chemische Berichte, 1941, vol. 74, p. 321,324
[3] Archiv der Pharmazie (Weinheim, Germany), 1932, vol. 270, p. 353,359
[4] Chemische Berichte, 1941, vol. 74, p. 321,324
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[2] Analytical Chemistry, 2018, vol. 90, # 15, p. 9301 - 9307
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3-(3,5-Dimethoxyphenyl)propionic acid

Similarity: 0.95

Chemical Structure| 1135-23-5

[ 1135-23-5 ]

3-(4-Hydroxy-3-methoxyphenyl)propanoic acid

Similarity: 0.93

Chemical Structure| 20637-08-5

[ 20637-08-5 ]

Methyl 4-(4-methoxyphenyl)butanoate

Similarity: 0.93

Chemical Structure| 2107-70-2

[ 2107-70-2 ]

3-(3,4-Dimethoxyphenyl)propionic acid

Similarity: 0.93

Chemical Structure| 6342-77-4

[ 6342-77-4 ]

3-(2-Methoxyphenyl)propanoic acid

Similarity: 0.93

Carboxylic Acids

Chemical Structure| 717-94-2

[ 717-94-2 ]

3-(3,5-Dimethoxyphenyl)propionic acid

Similarity: 0.95

Chemical Structure| 1135-23-5

[ 1135-23-5 ]

3-(4-Hydroxy-3-methoxyphenyl)propanoic acid

Similarity: 0.93

Chemical Structure| 2107-70-2

[ 2107-70-2 ]

3-(3,4-Dimethoxyphenyl)propionic acid

Similarity: 0.93

Chemical Structure| 6342-77-4

[ 6342-77-4 ]

3-(2-Methoxyphenyl)propanoic acid

Similarity: 0.93

Chemical Structure| 7021-11-6

[ 7021-11-6 ]

4-(4-Hydroxyphenyl)butanoic acid

Similarity: 0.92