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[ CAS No. 14473-91-7 ] {[proInfo.proName]}

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Chemical Structure| 14473-91-7
Chemical Structure| 14473-91-7
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Product Details of [ 14473-91-7 ]

CAS No. :14473-91-7 MDL No. :MFCD00004382
Formula : C9H7BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YEMUSDCFQUBPAL-SNAWJCMRSA-N
M.W :227.05 Pubchem ID :776461
Synonyms :

Calculated chemistry of [ 14473-91-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.81
TPSA : 37.3 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) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 2.84
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 2.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -3.27
Solubility : 0.121 mg/ml ; 0.000531 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.119 mg/ml ; 0.000523 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.433 mg/ml ; 0.00191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 14473-91-7 ]

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 [ 14473-91-7 ]

* 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.

  • Upstream synthesis route of [ 14473-91-7 ]
  • Downstream synthetic route of [ 14473-91-7 ]

[ 14473-91-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 14473-91-7 ]
  • [ 766-81-4 ]
Reference: [1] Chinese Journal of Chemistry, 2011, vol. 29, # 11, p. 2350 - 2354
  • 2
  • [ 14473-91-7 ]
  • [ 65537-54-4 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3 h;
Stage #2: With sodium hydroxide; water In diethyl ether
To suspension Of LiAlH4 (0.5 g, 1.3 mmol) in diethyl ether (25 mL) was added 3- bromocinnamic acid (83, 1.0 g, 4 mmol), in portions, at RT. The resulting suspension was stirred for 3 hours. The reaction was quenched by the successive addition of 15percent aq. NaOH solution (1 mL) and water. The resulting white suspension was filtered through a pad of Celite. The filter cake was washed with ether and then ethyl acetate. The filtrate was concentrated to afford crude 8 as yellow oil. Yield (0.7g, 74percent). 1H NMR (400 MHz, CDCl3) δ 7.10-7.35 (m, 4H), 3.65 (t, J = 6.5 Hz, 2H), 2.68 (t, J = 7.8 Hz, 2H), 1.82-1.91 (m, 2H).
Reference: [1] Patent: WO2009/5794, 2009, A2, . Location in patent: Page/Page column 196
[2] Tetrahedron Letters, 2015, vol. 56, # 8, p. 1045 - 1048
  • 3
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  • [ 65537-54-4 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 17, p. 6148 - 6149
  • 4
  • [ 14473-91-7 ]
  • [ 42287-90-1 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2215
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2612 - 2621
  • 5
  • [ 14473-91-7 ]
  • [ 41070-12-6 ]
YieldReaction ConditionsOperation in experiment
93% With trans-N,N'-dimethylcyclohexane-1,2-diamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide In 1,4-dioxane at 110℃; for 22 h; A Schlenk tube was charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), 3- bromocinnamic acid (228 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. Racemic trans-N,N'-dimethyl-1, 2-cyclohexanediamine (16 μL, 0.10 mmol, 10 molpercent), 1,1, 1,3, 3, [3-HEXAMETHYLDISILAZANE] (211 [I1L,] 1.00 mmol), and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 22 h. The resulting suspension was allowed to reach room temperature, poured into ether (20 mL), and washed with a solution of Na2S205 (100 mg) in 10percent aq [HC1] [(3X20] mL). The organic phase was dried [(NA2SO4)] and concentrated. The residue was dissolved in hot ethanol (5 mL), and hot water (5 mL) was added to the solution. The product was allowed to crystallize at 0 [C] for 15 h to provide 256 mg (93percent yield) of 3-iodocinnamic as pale yellow needles. Mp: [186-188 °C] (lit. 180- [182 °C] See Yuzikhin, [O.] S.; Vasil'ev, A. V.; Rudenko, A. P. [RUSS. J ORG. CLIENI.] 2000, 36, [1743). 1H] NMR (400 MHz, DMSO-d6): 8 12.47 (s, 1H), 8.08 (s, 1H), 7.77 (d, J= 7.8 Hz, 1 H), 7.72 (d, [J=] 7.8 Hz, [1H),] 7.52 (d, [J=] 16.0 Hz, 1 H), 7.22 (t, [J= 7.] 8 Hz, [1H),] 6.5 8 (d, J = 16.0 Hz, 1H). [13C] NMR (100 MHz, DMSO-d6) : 8 167.3, 142.3, 138.6, 136.6, 136.5, 130.9, 127.4, 120.6, 95.4.
Reference: [1] Patent: WO2004/13094, 2004, A2, . Location in patent: Page 81
[2] Journal of the American Chemical Society, 2002, vol. 124, # 50, p. 14844 - 14845
  • 6
  • [ 3132-99-8 ]
  • [ 141-82-2 ]
  • [ 14473-91-7 ]
  • [ 117391-50-1 ]
Reference: [1] Russian Journal of General Chemistry, 2005, vol. 75, # 7, p. 1113 - 1124
  • 7
  • [ 14473-91-7 ]
  • [ 82827-09-6 ]
Reference: [1] Patent: US6034093, 2000, A,
[2] Patent: US5731315, 1998, A,
[3] Patent: US2011/111046, 2011, A1,
[4] Patent: WO2011/58473, 2011, A1,
  • 8
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9152 - 9157
[2] Tetrahedron, 2016, vol. 72, # 46, p. 7343 - 7347
  • 9
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Catalysis Science and Technology, 2016, vol. 6, # 12, p. 4086 - 4089
  • 10
  • [ 117391-50-1 ]
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
  • 11
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 12
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 13
  • [ 14473-91-7 ]
  • [ 82311-69-1 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12977 - 12983
  • 14
  • [ 14473-91-7 ]
  • [ 82278-73-7 ]
Reference: [1] Catalysis Science and Technology, 2016, vol. 6, # 12, p. 4086 - 4089
  • 15
  • [ 14473-91-7 ]
  • [ 151583-29-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2612 - 2621
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