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Chemical Structure| 29823-21-0
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Product Details of [ 29823-21-0 ]

CAS No. :29823-21-0 MDL No. :MFCD00045057
Formula : C10H19BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :UBTQVPMVWAEGAC-UHFFFAOYSA-N
M.W : 251.16 Pubchem ID :264813
Synonyms :

Calculated chemistry of [ 29823-21-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 9
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.34
TPSA : 26.3 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) : -5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.29
Log Po/w (XLOGP3) : 3.4
Log Po/w (WLOGP) : 3.29
Log Po/w (MLOGP) : 3.01
Log Po/w (SILICOS-IT) : 3.4
Consensus Log Po/w : 3.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.95
Solubility : 0.285 mg/ml ; 0.00113 mol/l
Class : Soluble
Log S (Ali) : -3.63
Solubility : 0.0587 mg/ml ; 0.000234 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.05
Solubility : 0.0223 mg/ml ; 0.0000887 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.57

Safety of [ 29823-21-0 ]

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 [ 29823-21-0 ]

* 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 [ 29823-21-0 ]
  • Downstream synthetic route of [ 29823-21-0 ]

[ 29823-21-0 ] Synthesis Path-Upstream   1~14

  • 1
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Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
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  • [ 4101-68-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 3
  • [ 29823-21-0 ]
  • [ 17696-11-6 ]
YieldReaction ConditionsOperation in experiment
97% With water; sodium hydroxide In ethanol at 0℃; for 5 h; To a solution of ethyl 8-bromooctanoate (1.0 g, 3.98mmol) in EtOH (10 mL), 1M NaOH (3.98 mL) was addeddropwise, and the resulting mixture was stirred at 0°C for 5h. The mixture was acidified with 1M HCl and extractedwith ethyl acetate (3 10 mL). The organic layer waswashed with satd NaHCO3 (2 20 mL) and brine (2 20mL), dried over Na2SO4, filtered, and concentrated to getcompound 17 as colorless oil 0.86 g, yield 97percent.
Reference: [1] Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3312 - 3320
[2] Medicinal Chemistry, 2013, vol. 9, # 2, p. 294 - 302
  • 4
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YieldReaction ConditionsOperation in experiment
98% for 3 h; Heating / reflux To a solution of 8-bromooctanoic acid (5.0 g, 22 mmol) in ethanol (100 ML) was added H2SO4 (0.36 ML, 7.5 mmol) and the reaction was heated to reflux with stirring for 3 h.The crude reaction mixture was cooled to room temperature and washed H2O (100 ML), sat. NaHCO3 (2*100 ML), H2O (100 ML), dried MgSO4, and evaporated to dryness to afford a clear oil (5.5 g, 98percent yield).
98% for 3 h; Heating / reflux To a solution of monodispersed 8-bromooctanoic acid (5.0 g, 22 mmol) in ethanol (100 mL) was added H2SO4 (0.36 mL, 7.5 mmol) and the reaction was heated to reflux with stirring for 3 h. The crude reaction mixture was cooled to room temperature and washed H2O (100 mL), sat. NaHCO3 (2.x.100 mL), H2O (100 mL), dried MgSO4, and evaporated to dryness to afford a clear oil 11 (5.5 g, 98percent yield).
75% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12 h; To a solution of 8-bromooctanoic acid (0.20 g, 0.89 mmol), DMAP (0.12 g, 0.99 mmol), and ethanol (0.05 g, 0.99 mmol) in methylene chloride (20 mL) was added EDCI (0.19 g, 0.99 mmol) at room temperature. After stirring for 12 h, the reaction mixture was washed with 1 N NaOH aqueous solution (15 mL) and water (30 mL), and the organic layer was dried over Na2SO4 and evaporated to give 8-bromooctanoic acid ethyl ester (0.17 g, 75percent). This bromide reacted with 4-(3-adamantan-l-yl-ureido)butyric acid 822 in the same manner as that used for the preparation of 883 to provide 879 (0.19 g, 65percent) as a solid: 1H EPO <DP n="59"/>NMR (CDCl3) 1.26 (3H, t, J = 6.9 Hz), 1.32-1.35 (6H, m), 1.59-1.66 (1OH, m), 1.82 (2H, quint, J - 6.9 Hz), 1.94-1.97 (6H, m), 2.05-2.07 (3H, m), 2.28 (2H, t, J = 6.9 Hz), 2.36 (2H, t, J = 6.9 Hz), 3.16 (2H, q, J = 6.9 Hz), 4.05-4.14 (5H, m), 4.31 (IH, s); LC-MS (ESI) m/z calcd for C25H42N2O5 [M + H]+ 451.31, found [M + H]+ 451.20; mp 58-59 C. Anal. (C25H42N2O5) C, H, N.
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 2, p. 301 - 303
[2] Patent: US2003/228275, 2003, A1, . Location in patent: Page 42
[3] Patent: US2003/229009, 2003, A1, . Location in patent: Page 38
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 563 - 566
[5] Synthesis, 1998, # 11, p. 1662 - 1669
[6] Synthesis, 2007, # 22, p. 3489 - 3496
[7] Carbohydrate Research, 2001, vol. 330, # 3, p. 295 - 307
[8] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2110 - 2122
[9] Patent: WO2006/45119, 2006, A2, . Location in patent: Page/Page column 57-58
[10] Bulletin de la Societe Chimique de France, 1956, p. 1345,1350
[11] Chinese Journal of Chemistry, 2014, vol. 32, # 2, p. 157 - 162
[12] ACS Chemical Neuroscience, 2017, vol. 8, # 9, p. 1949 - 1959
  • 5
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YieldReaction ConditionsOperation in experiment
94% With phosphoric acid In ethanol; water; benzene (4)
Production of ethyl 8-bromocaprylate
A 500-ml flask equipped with a liquid-liquid separating device for separation of water was charged with 100 g (0.45 mole) of 8-bromocaprylic acid, 100 ml of ethanol, 300 ml of benzene and 10 g of phosphoric acid, and the reaction was allowed to proceed under azeotropic removal of water for 6 hours.
Thereafter, 200 ml of water and 200 ml of benzene were added to the liquid reaction mixture for extraction.
The benzene layer was washed with two 100-ml portions of water and then dried over anhydrous sodium sulfate.
After the benzene was distilled off, the residual liquid was distilled under reduced pressure to give 106 g (94percent yield based on the charged 8-bromocaprylic acid) of ethyl 8-bromocaprylate as a fraction boiling at 124°-125° C./4 mmHg.
Reference: [1] Patent: US4510331, 1985, A,
  • 6
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YieldReaction ConditionsOperation in experiment
93% at 20℃; Inert atmosphere To an ice-salt-cooled solution of 10 g (45 mmol) of 8-bromooctanoic acid in 180 mL of ethanol is added slowly 9 mL of acetyl chloride (127 mmol) under Ar. The resulting mixture was stirred for 20 min before removing the cooling bath. The solution is allowed to stand overnight at room temperature (20 h). Solvent was removed under reduced pressure. The residual oil was dissolved in hexanes (200 mL) and washed with dilute sodium bicarbonate twice (2 x 70 mL). The aqueous phase was extracted with hexanes (100 mL). The combined organic solution was washed with brine (2 x 70 mL), dried over sodium sulfate, filtered and concentrated to give a corlorless oil (10.49 g, 41.8 mmol, 93percent).
Reference: [1] Patent: WO2013/86322, 2013, A1, . Location in patent: Page/Page column 50; 51
  • 7
  • [ 1593-55-1 ]
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Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 7, p. 2440 - 2445
[2] Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3312 - 3320
[3] Justus Liebigs Annalen der Chemie, 1961, vol. 641, p. 63 - 70
  • 8
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Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 9
  • [ 123-99-9 ]
  • [ 29823-21-0 ]
Reference: [1] Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3312 - 3320
  • 10
  • [ 624-17-9 ]
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Reference: [1] Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3312 - 3320
  • 11
  • [ 4117-09-3 ]
  • [ 29823-21-0 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 12
  • [ 64-17-5 ]
  • [ 17696-11-6 ]
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  • [ 7732-18-5 ]
Reference: [1] Patent: EP1384706, 2004, A1, . Location in patent: Page/Page column 6
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Reference: [1] Bulletin de la Societe Chimique de France, 1956, p. 1345,1350
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Reference: [1] Bulletin de la Societe Chimique de France, 1956, p. 1345,1350
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