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[ CAS No. 7417-21-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 7417-21-2
Chemical Structure| 7417-21-2
Chemical Structure| 7417-21-2
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Product Details of [ 7417-21-2 ]

CAS No. :7417-21-2 MDL No. :MFCD00002894
Formula : C10H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SRQAJMUHZROVHW-UHFFFAOYSA-N
M.W : 182.22 Pubchem ID :81911
Synonyms :

Calculated chemistry of [ 7417-21-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.36
TPSA : 38.69 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) : -6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 1.03
Log Po/w (WLOGP) : 1.24
Log Po/w (MLOGP) : 1.22
Log Po/w (SILICOS-IT) : 2.03
Consensus Log Po/w : 1.54

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.7
Solubility : 3.67 mg/ml ; 0.0201 mol/l
Class : Very soluble
Log S (Ali) : -1.43
Solubility : 6.73 mg/ml ; 0.0369 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.89
Solubility : 0.236 mg/ml ; 0.0013 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 7417-21-2 ]

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 [ 7417-21-2 ]

* 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 [ 7417-21-2 ]
  • Downstream synthetic route of [ 7417-21-2 ]

[ 7417-21-2 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 7417-21-2 ]
  • [ 120-20-7 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 2, p. 484 - 487
  • 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
  • [ 406215-61-0 ]
  • [ 7417-21-2 ]
YieldReaction ConditionsOperation in experiment
97% With toluene-4-sulfonic acid In methanol; dichloromethane at 20 - 25℃; for 0.333333 h; Flow reactor General procedure: The system (Figure 4) was primed with solvent (DCM and 0.3 M aqueous NaOH) prior to the introduction of the substrates. Substrates were present as 0.034 M solutions (20 mL) in glass vials. These were placed in a square 4 x 4 rack. Following initiation of the computer-vision system (and checking to make sure the aqueous-out tap was opening/closing properly), activation of the autosampler/liquid-handling schedule was initiated by pressing ‘s’ on the computer keyboard. The outlet of the flow stream for each product was then collected until the autosampler moved to the waste position between each run. 5 mL of substrate was taken up during each run, 4 mL of which entered the holding loop (the line between the autosampler and 3-way-valve 1 was 1 mL in volume). Outlet collection flasks were changed manually. The products were isolated by removing solvent under reduced pressure.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 25, p. 2409 - 2413
  • 4
  • [ 75-21-8 ]
  • [ 2859-78-1 ]
  • [ 7417-21-2 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With iodine; magnesium In tetrahydrofuran at 70℃; Inert atmosphere; Reflux
Stage #2: at 0 - 70℃; Inert atmosphere
Stage #3: With ammonium chloride In tetrahydrofuranInert atmosphere
Example 2: Preparation of 2-(3.4-dimethoxyphenyl)ethanol (2) from 4-bromo-l ,2- dimethoxybenzene (1)Magnesium turnings (3.9 g, 0.160 mol, 1.0 equiv) and I2 (5 mg) was charged to a 250 mL three- neck round-bottom flask, one neck of which was equipped with a cooling condenser, one with a dropping funnel, the other with a thermometer. The reaction system was protected with N2 gas. A small portion of 4-bromo-l,2-dimethoxybenzene (35 g, 0.155 mol) in anhydrous THF (160 mL) was added to the flask. After the reaction was initiated by heating the reaction mixture at 70 °C, the residual solution of the bromide was added slowly at a rate sufficient to maintain the reaction solution under slight reflux. When the addition was finished, the mixture was maintained at 70 °C for 2 h and then cooled to 0 °C. Ethylene oxide (15 mL, 0.30 mol, 2.0 equiv) was added dropwise and the reaction mixture was heated to 70 °C for 1 h. When a sticky gel hat formed, a saturated NH4CI solution (100 mL) was added. After phase separation, the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were washed with water (2 * 50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to give a red oil. Distillation yielded a colorless oil (15.3 g, b.p. 155-160 °C/10 mbar, 55percent), which solidified upon standing. 3/4 NMR (400 MHz, DMSO-^): δ 6.83 (d, J= 8.2 Hz, 1 H), 6.80 (d, J= 2.0 Hz, 1 H), 6.71 (dd, J= 8.2, 2.0 Hz, 1 H), 4.60 (t, J= 5.2 Hz, 1 H, -OH), 3.73 (s, 3 H), 3.70 (s, 3 H), 3.57 (m, 2 H), 2.65 (t, J= 7.2 Hz, 2 H). 13C MR (100 MHz, DMSO-afc): δ 148.7, 147.2, 132.1, 120.7, 113.0, 112.0, 62.5, 55.6, 55.4, 38.7.
Reference: [1] Patent: WO2012/6783, 2012, A1, . Location in patent: Page/Page column 12
  • 5
  • [ 15964-79-1 ]
  • [ 7417-21-2 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 42, p. 8914 - 8920
[2] Journal of Organic Chemistry, 1961, vol. 26, p. 1754 - 1758
[3] Journal of Organic Chemistry, 1964, vol. 29, p. 2372 - 2378
[4] Phytochemistry (Elsevier), 1987, vol. 26, # 5, p. 1453 - 1458
[5] Synthesis, 1999, # 5, p. 885 - 897
[6] Synthesis, 2011, # 18, p. 2935 - 2940
  • 6
  • [ 6380-23-0 ]
  • [ 7417-21-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8422 - 8440
[2] Chemical Biology and Drug Design, 2011, vol. 78, # 1, p. 101 - 111
  • 7
  • [ 5703-21-9 ]
  • [ 7417-21-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1958, vol. 6, p. 574
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 3114,3117
[3] Organic Letters, 2014, vol. 16, # 2, p. 484 - 487
  • 8
  • [ 120-20-7 ]
  • [ 7417-21-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1949, vol. 563, p. 86,89
[2] Journal of the American Chemical Society, 1931, vol. 53, p. 2192,2195,2198
  • 9
  • [ 186581-53-3 ]
  • [ 10597-60-1 ]
  • [ 7417-21-2 ]
Reference: [1] Gazzetta Chimica Italiana, 1960, vol. 90, p. 1449 - 1485
[2] Phytochemistry (Elsevier), 1990, vol. 29, # 9, p. 2905 - 2912
  • 10
  • [ 14617-41-5 ]
  • [ 7417-21-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1972, p. 4145 - 4148
[2] Chemical and Pharmaceutical Bulletin, 1960, vol. 8, p. 266 - 269
  • 11
  • [ 102-32-9 ]
  • [ 7417-21-2 ]
Reference: [1] Phytochemistry (Elsevier), 1987, vol. 26, # 5, p. 1453 - 1458
  • 12
  • [ 25379-88-8 ]
  • [ 7417-21-2 ]
Reference: [1] Phytochemistry (Elsevier), 1987, vol. 26, # 5, p. 1453 - 1458
  • 13
  • [ 91-16-7 ]
  • [ 7417-21-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1972, p. 4145 - 4148
[2] Patent: WO2012/6783, 2012, A1,
  • 14
  • [ 64-17-5 ]
  • [ 18066-68-7 ]
  • [ 7417-21-2 ]
Reference: [1] Journal of the Chemical Society, 1933, p. 1463,1464
[2] Justus Liebigs Annalen der Chemie, 1949, vol. 563, p. 86,89
  • 15
  • [ 6275-29-2 ]
  • [ 7417-21-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1960, vol. 8, p. 266 - 269
  • 16
  • [ 121-33-5 ]
  • [ 7417-21-2 ]
Reference: [1] Chemical Biology and Drug Design, 2011, vol. 78, # 1, p. 101 - 111
[2] Chemical Biology and Drug Design, 2011, vol. 78, # 1, p. 101 - 111
  • 17
  • [ 7786-61-0 ]
  • [ 7417-21-2 ]
Reference: [1] Chemical Biology and Drug Design, 2011, vol. 78, # 1, p. 101 - 111
  • 18
  • [ 120-14-9 ]
  • [ 7417-21-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8422 - 8440
  • 19
  • [ 10597-60-1 ]
  • [ 77-78-1 ]
  • [ 7417-21-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1949, vol. 563, p. 86,89
  • 20
  • [ 18066-68-7 ]
  • [ 7417-21-2 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 4252,4254
[2] Journal of the Chemical Society, 1959, p. 2157,2163
  • 21
  • [ 13267-96-4 ]
  • [ 7417-21-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1958, vol. 6, p. 574
  • 22
  • [ 81316-62-3 ]
  • [ 7417-21-2 ]
Reference: [1] Journal of the Chemical Society, 1959, p. 2157,2163
  • 23
  • [ 109-72-8 ]
  • [ 2859-78-1 ]
  • [ 7417-21-2 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 4252,4254
  • 24
  • [ 60561-55-9 ]
  • [ 7417-21-2 ]
Reference: [1] Synthetic Communications, 1976, vol. 6, p. 349 - 355
  • 25
  • [ 67-56-1 ]
  • [ 112693-26-2 ]
  • [ 53955-97-8 ]
  • [ 4117-96-8 ]
  • [ 4348-80-5 ]
  • [ 7417-21-2 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 10, p. 4155 - 4161
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