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[ CAS No. 93-40-3 ] {[proInfo.proName]}

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Chemical Structure| 93-40-3
Chemical Structure| 93-40-3
Structure of 93-40-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 93-40-3 ]

CAS No. :93-40-3 MDL No. :MFCD00004335
Formula : C10H12O4 Boiling Point : -
Linear Structure Formula :- InChI Key :WUAXWQRULBZETB-UHFFFAOYSA-N
M.W : 196.20 Pubchem ID :7139
Synonyms :

Calculated chemistry of [ 93-40-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.97
TPSA : 55.76 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) : -6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : 1.33
Log Po/w (MLOGP) : 1.09
Log Po/w (SILICOS-IT) : 1.59
Consensus Log Po/w : 1.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.71
Solubility : 3.84 mg/ml ; 0.0196 mol/l
Class : Very soluble
Log S (Ali) : -1.71
Solubility : 3.84 mg/ml ; 0.0196 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.721 mg/ml ; 0.00367 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 93-40-3 ]

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

Application In Synthesis of [ 93-40-3 ]

* 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 [ 93-40-3 ]
  • Downstream synthetic route of [ 93-40-3 ]

[ 93-40-3 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 93-40-3 ]
  • [ 13575-75-2 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 47, p. 24619 - 24634
[2] RSC Advances, 2014, vol. 4, # 47, p. 24619 - 24634
  • 2
  • [ 93-40-3 ]
  • [ 7417-21-2 ]
YieldReaction ConditionsOperation in experiment
98.9% With sodium tetrahydroborate; iodine In tetrahydrofuran at 20℃; for 0.583333 h; Cooling with ice Take a dry and clean 100 mL round bottom flask, accurately weigh sodium borohydride (0.4 g, 7.65 mmol) and iodine (1.3 g, 5.10 mmol) in a bottle, add 10 mL of tetrahydrofuran, place in an ice bath, stir After 5 min, 21 (1.0 g, 5.10 mmol) was added in small portions. After the addition, the ice bath was removed and the reaction was carried out at room temperature. The reaction was monitored by TLC. After 30 min, the reaction was completed by TLC. 50 ml of a 5percent sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 mL × 3), and the organic phase was combined and washed with brine (10 mL × 3). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporatedThe title compound (22) was obtained as a yellow oil.The yield was 98.9percent.
Reference: [1] Patent: CN108484593, 2018, A, . Location in patent: Paragraph 0050; 0051; 0065
[2] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5289 - 5295
[3] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 2213 - 2216
[4] Journal of Organic Chemistry, 2004, vol. 69, # 7, p. 2362 - 2366
[5] European Journal of Organic Chemistry, 2008, # 27, p. 4622 - 4631
[6] Journal of the American Chemical Society, 2011, vol. 133, # 43, p. 17142 - 17145
[7] Journal of the Chemical Society, 1959, p. 2157,2163
[8] Phytochemistry (Elsevier), 1983, vol. 22, # 9, p. 1941 - 1944
[9] Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 358 - 378
[10] Journal of the Chemical Society, 1933, p. 1463,1464
[11] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6539 - 6542
[12] Angewandte Chemie - International Edition, 2010, vol. 49, # 25, p. 4278 - 4281
[13] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 23, p. 8324 - 8333
[14] Synthesis, 2011, # 18, p. 2935 - 2940
[15] Tetrahedron, 2013, vol. 69, # 42, p. 8914 - 8920
[16] Journal of the American Chemical Society, 2014, vol. 136, # 20, p. 7205 - 7208
[17] Angewandte Chemie - International Edition, 2014, vol. 53, # 52, p. 14555 - 14558[18] Angew. Chem., 2014, vol. 126, # 52, p. 14783 - 14786,4
[19] Angewandte Chemie - International Edition, 2015, vol. 54, # 45, p. 13357 - 13361[20] Angew. Chem., 2015, vol. 127, # 45, p. 13555 - 13559,5
[21] Chemical Biology and Drug Design, 2016, p. 599 - 607
[22] Patent: US6518315, 2003, B1,
  • 3
  • [ 93-40-3 ]
  • [ 776-99-8 ]
Reference: [1] Yakugaku Kenkyu, 1958, vol. 30, p. 185,191[2] Chem.Abstr., 1960, p. 1517
  • 4
  • [ 67-56-1 ]
  • [ 93-40-3 ]
  • [ 15964-79-1 ]
YieldReaction ConditionsOperation in experiment
96% Reflux Methyl 2-(3,4-dimethoxyphenyl)acetate SLA 28134
To a solution of 2-(3,4-dimethoxyphenyl)acetic acid (25.0 g, 127.4 mmol) in MeOH (100 mL) in a 500 mL round-bottomed flask equipped with a magnetic stirrer was added a catalytic amount of sulfuric acid (around 10 drops) and the mixture was stirred overnight under reflux.
After cooling to RT, MeOH was removed at 40° C. under vacuum and the product was taken up in CH2Cl2 (250 mL), washed with water (5*20 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give methyl 2-(3,4-dimethoxyphenyl)acetate SLA 28134 as an orange oil (25.77 g, 96percent yield).
MW: 210.23; Yield: 96percent; Orange oil.
Rf: 0.25 (cyclohexane:EtOAc=3:1).
1H-NMR (CDCl3, δ): 3.56 (s, 2H, CH2), 3.70 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 6.82-6.83 (m, 3H, 3*ArH).
13C-NMR (CDCl3, δ): 40.6, 51.9, 55.8 (2*C), 111.2, 112.4, 121.4, 126.4, 148.2, 148.9, 172.2.
MS-ESI m/z (percent rel. Int.): 233.2 ([M+Na]+, 3), 151.1 (100).
93.3%
Stage #1: With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1 h;
Stage #2: at 20℃; for 1 h;
To a 1 L three-necked flask was added Compound 7a (50 g, 0.255 mol), 250 ml of dichloromethane,Stir at room temperature,Carbonyldiimidazole (62 g, 0.382 mol) was added in batches and reacted for 1 h at room temperature.Add 50ml of methanol, stir for 1h,The reaction solution was poured into a separatory funnel, 200 ml of water was added for extraction, and the organic layer was collected and dried over anhydrous sodium sulfate.The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to give 50 g of compound 6a in a yield of 93.3percent.
88% at 120℃; for 0.333333 h; Microwave irradiation General procedure: In a typical reaction, AMA 2:3 (332 g, 0.6 mol), the corresponding carboxylicacid (1 mol), and alcohol (1.5–2 mol) were mixed in the provided reaction glass tubeequipped with a screw cap and magnetic agitation until a wet mixture was achieved.The reaction mixture was irradiated with microwaves (Anton Parr Monowave 300reactor) at 80 C for 8 min or 120 C for 20 min. On cooling, the mixture was diluted with dichloromethane (41 mL), filtered under gravity, and washed with dichloromethane;then the filtrate was washed with Na2CO3 (ss) and water. The organic layerwas dried over Na2SO4, filtered, and concentrated under reduced pressure to give theester.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 1, p. 85 - 90
[2] Tetrahedron, 2007, vol. 63, # 46, p. 11377 - 11385
[3] Tetrahedron, 2013, vol. 69, # 42, p. 8914 - 8920
[4] Patent: US2012/214837, 2012, A1, . Location in patent: Page/Page column 23-24
[5] Journal of Organic Chemistry, 2003, vol. 68, # 3, p. 1165 - 1167
[6] Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3491 - 3499
[7] Journal of Organic Chemistry, 1990, vol. 55, # 4, p. 1261 - 1266
[8] Patent: CN105153105, 2018, B, . Location in patent: Paragraph 0068-0070
[9] Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6808 - 6815
[10] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5594 - 5598
[11] Journal of Medicinal Chemistry, 2012, vol. 55, # 24, p. 10863 - 10884
[12] Synthetic Communications, 2014, vol. 44, # 16, p. 2386 - 2392
[13] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10246 - 10253
[14] Tetrahedron Letters, 1996, vol. 37, # 8, p. 1233 - 1236
[15] Archiv der Pharmazie (Weinheim, Germany), 1933, vol. 271, p. 431,435
[16] Tetrahedron, 1992, vol. 48, # 38, p. 8285 - 8294
[17] Patent: US2007/287708, 2007, A1, . Location in patent: Page/Page column 28
[18] Patent: US2007/287738, 2007, A1, . Location in patent: Page/Page column 17
[19] Synthetic Communications, 2008, vol. 38, # 21, p. 3662 - 3671
[20] Synthesis, 2011, # 18, p. 2935 - 2940
[21] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6567 - 6572
[22] Patent: WO2012/145234, 2012, A2, . Location in patent: Page/Page column 31-32
[23] Journal of the American Chemical Society, 2013, vol. 135, # 18, p. 6774 - 6777
[24] Patent: EP2871187, 2015, A1, . Location in patent: Paragraph 0063-0064
[25] Patent: US2015/183797, 2015, A1, . Location in patent: Paragraph 0160-0162
[26] Chemistry - A European Journal, 2015, vol. 21, # 36, p. 12601 - 12605
[27] Tetrahedron Letters, 2016, vol. 57, # 8, p. 849 - 851
  • 5
  • [ 93-40-3 ]
  • [ 15964-79-1 ]
Reference: [1] Patent: US6630597, 2003, B1,
  • 6
  • [ 186581-53-3 ]
  • [ 93-40-3 ]
  • [ 15964-79-1 ]
Reference: [1] Chemical Communications, 2009, # 13, p. 1739 - 1741
  • 7
  • [ 93-40-3 ]
  • [ 7664-93-9 ]
  • [ 15964-79-1 ]
Reference: [1] Patent: US5219848, 1993, A,
  • 8
  • [ 93-40-3 ]
  • [ 64-17-5 ]
  • [ 18066-68-7 ]
YieldReaction ConditionsOperation in experiment
90% at 120℃; for 0.333333 h; Microwave irradiation General procedure: In a typical reaction, AMA 2:3 (332 g, 0.6 mol), the corresponding carboxylicacid (1 mol), and alcohol (1.5–2 mol) were mixed in the provided reaction glass tubeequipped with a screw cap and magnetic agitation until a wet mixture was achieved.The reaction mixture was irradiated with microwaves (Anton Parr Monowave 300reactor) at 80 C for 8 min or 120 C for 20 min. On cooling, the mixture was diluted with dichloromethane (41 mL), filtered under gravity, and washed with dichloromethane;then the filtrate was washed with Na2CO3 (ss) and water. The organic layerwas dried over Na2SO4, filtered, and concentrated under reduced pressure to give theester.
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1586 - 1605
[2] Journal of Organic Chemistry, 2003, vol. 68, # 3, p. 1165 - 1167
[3] Synthetic Communications, 2014, vol. 44, # 16, p. 2386 - 2392
[4] Journal of Organic Chemistry, 2010, vol. 75, # 19, p. 6549 - 6562
[5] Tetrahedron, 1997, vol. 53, # 30, p. 10555 - 10564
[6] Journal of the Chemical Society, 1933, p. 1463,1464
[7] Journal of Fluorine Chemistry, 1990, vol. 49, # 1, p. 115 - 126
[8] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 9, p. 1732 - 1738[9] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 9, p. 1954 - 1961
[10] Tetrahedron Letters, 1996, vol. 37, # 8, p. 1233 - 1236
  • 9
  • [ 93-40-3 ]
  • [ 18066-68-7 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, p. 51
  • 10
  • [ 93-40-3 ]
  • [ 64228-81-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 1981, vol. 16, # 6, p. 515 - 524
  • 11
  • [ 93-40-3 ]
  • [ 6429-04-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 1981, vol. 16, # 6, p. 515 - 524
[2] Heterocycles, 2014, vol. 8, # 2, p. 1311 - 1321
  • 12
  • [ 93-40-3 ]
  • [ 73942-87-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 5, p. 1496 - 1504
[2] Chemical Biology and Drug Design, 2016, p. 599 - 607
[3] Patent: WO2017/138017, 2017, A1,
  • 13
  • [ 93-40-3 ]
  • [ 85175-59-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 5, p. 1496 - 1504
[2] Patent: WO2017/138017, 2017, A1,
  • 14
  • [ 93-40-3 ]
  • [ 148849-67-6 ]
Reference: [1] Patent: WO2017/138017, 2017, A1,
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