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[ CAS No. 129150-68-1 ] {[proInfo.proName]}

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Chemical Structure| 129150-68-1
Chemical Structure| 129150-68-1
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Product Details of [ 129150-68-1 ]

CAS No. :129150-68-1 MDL No. :MFCD24448669
Formula : C13H19NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OWIZBOBVXITREP-UHFFFAOYSA-N
M.W : 237.30 Pubchem ID :11031911
Synonyms :

Calculated chemistry of [ 129150-68-1 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 66.79
TPSA : 58.56 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 2.07
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 2.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.403 mg/ml ; 0.0017 mol/l
Class : Soluble
Log S (Ali) : -3.41
Solubility : 0.0931 mg/ml ; 0.000392 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.59
Solubility : 0.061 mg/ml ; 0.000257 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 129150-68-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 129150-68-1 ]

* 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 [ 129150-68-1 ]
  • Downstream synthetic route of [ 129150-68-1 ]

[ 129150-68-1 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 132513-29-2 ]
  • [ 129150-68-1 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethanol Step B [2-(3-Hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester; 1 g of Pd/C 10percent was added to a solution of 13 g (0.039 mol) of [2-(3-benzyloxy-phenyl)- ethyl]-carbamic acid tert-butyl ester in 100 ml of ethanol. The mixture was hydrogenated at 40 psi overnight. The catalyst was filtered off and washed with ethanol. The solvent was removed under vacuum and 9.4 g of the title compound were obtained as a colourless oil in quantitative yield.1H-NMR CDCl3: 7.22-7.12 (m, IH); 6.78-6.66 (m, 3H); 4.56 (bs, IH); 3.42-3.30 (m, 2H); 2.74 (t, 2H); 1.44 (S, 9H).
98% With palladium on activated charcoal; hydrogen In methanol at 20℃; Inert atmosphere A round-bottomed flask fitted with stir bar was charged with tert-butyl {2-[3- (benzyloxy)phenyl]ethyl}carbamate (Intermediate 68; 1 .43g, 0.OO4mol)in MeOH (5OmL) The flask was filled with Argon, and then Pd/C (143mg, O.OOlmol) was added employing an Argon cone stream to avoid solvent ignition. The flask was coupled with a quick-fit T-adaptor with one outlet to the hydrogen balloon and the other to the vacuum line. The flask was emptied by connecting it to the vacuum and then filled with hydrogen. This op-eration was repeated twice. The reaction mixture was stirred overnight at room tempera-ture. The solid was filtered through a Celite pad and concentrated under reduced pressure to give the title compound as a white solid (980mg, 98percent).LRMS (m/z): 238 (M+1)+
Reference: [1] Patent: WO2007/71311, 2007, A1, . Location in patent: Page/Page column 55-56
[2] Patent: WO2014/95920, 2014, A1, . Location in patent: Page/Page column 70
[3] Journal of Organic Chemistry, 1990, vol. 55, # 24, p. 6000 - 6017
[4] Patent: WO2009/68177, 2009, A1, . Location in patent: Page/Page column 39
[5] Patent: US2010/210631, 2010, A1, . Location in patent: Page/Page column 14
[6] Patent: WO2008/151702, 2008, A1, . Location in patent: Page/Page column 33
  • 2
  • [ 24424-99-5 ]
  • [ 2039-67-0 ]
  • [ 129150-68-1 ]
YieldReaction ConditionsOperation in experiment
95.3% With sodium hydroxide; hydrogen bromide In diethyl ether (1)
A mixture of 3-methoxyphenethylamine (21.9 ml, 150 mmols) and 47 percent hydrobromic acid (100 ml) was stirred, while being heated under reflux, for 10 hours.
The reaction mixture was cooled, and the solvent was evaporated away under reduced pressure.
The residue was poured into water.
To the resulting mixture, added was an aqueous solution (100 ml) of sodium hydroxide (6 g, 150 mmols), and stirred at room temperature for 30 minutes.
Next, a diethyl ether solution (100 ml) of di-tert-butyl dicarbonate (32.7 g, 0.15 mmols) was dropwise added thereto at 0°C over a period of 2 hours.
The reaction mixture was stirred at 0°C for 12 hours, and then extracted with diethyl ether.
The extract was washed with brine, and then dried with anhydrous magnesium sulfate.
This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give a crystal of N-tert-butoxycarbonyl-3-hydroxyphenethylamine (33.4 g, 95.3 percent).
m.p. 84-85°C
1H-NMR (CDCl3) δ: 1.44(9H,s), 2,72(2H,t,J=6.8Hz), 3.32-3.42(2H,m), 4.65(1H,bs), 6.56(1H,bs), 6.70-6.76(3H,m),
Reference: [1] Patent: EP1123918, 2001, A1,
[2] Patent: US2004/6143, 2004, A1,
[3] Patent: WO2008/151702, 2008, A1, . Location in patent: Page/Page column 33
  • 3
  • [ 24424-99-5 ]
  • [ 588-05-6 ]
  • [ 129150-68-1 ]
YieldReaction ConditionsOperation in experiment
58.6% With potassium carbonate In water at 23℃; for 24 h; General procedure: Serotonin creatinine sulfate monohydrate (1.0 equiv, 18.8 mmol) orthe appropriate scaffold was dissolved in H2O (80 mL). Potassiumcarbonate (2.0 equiv, 37.6 mmol) was added all at once and reaction was stirredwith a dry stir bar. Di-tert-butyl dicarbonate (1.0 equiv, 18.8 mmol) was addedall at once via syringe and reaction was stirred for 24 hours at 23°C exposedto the atmosphere (no argon). The product was then extracted with 3x10 mL EtOAcand then washed with 20 mL of H2O, 20 mL of 5percent HCl, and 20 mL of brine.The organic portion was then filtered through MgSO4 and solvent wasevaporated off under reduced pressure, leaving a sticky green solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5539 - 5544
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 24, p. 5260 - 5279
[3] Patent: WO2009/68177, 2009, A1, . Location in patent: Page/Page column 28
[4] Patent: US2010/210631, 2010, A1, . Location in patent: Page/Page column 14
[5] Tetrahedron, 2013, vol. 69, # 1, p. 242 - 256
[6] Patent: US2013/237524, 2013, A1, . Location in patent: Paragraph 0214
[7] Chemical Communications, 2015, vol. 51, # 20, p. 4231 - 4233
  • 4
  • [ 24424-99-5 ]
  • [ 3458-98-8 ]
  • [ 129150-68-1 ]
Reference: [1] Patent: WO2007/107828, 2007, A2, . Location in patent: Page/Page column 58
  • 5
  • [ 24424-99-5 ]
  • [ 38449-59-1 ]
  • [ 129150-68-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5351 - 5381
  • 6
  • [ 621-54-5 ]
  • [ 129150-68-1 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 24, p. 6000 - 6017
  • 7
  • [ 57668-34-5 ]
  • [ 129150-68-1 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 24, p. 6000 - 6017
  • 8
  • [ 24424-99-5 ]
  • [ 3458-98-8 ]
  • [ 144-55-8 ]
  • [ 129150-68-1 ]
Reference: [1] Patent: US5874436, 1999, A,
  • 9
  • [ 24424-99-5 ]
  • [ 129150-68-1 ]
Reference: [1] Patent: WO2014/95920, 2014, A1,
[2] Patent: WO2008/151702, 2008, A1,
  • 10
  • [ 29973-97-5 ]
  • [ 129150-68-1 ]
Reference: [1] Patent: WO2008/151702, 2008, A1,
  • 11
  • [ 2039-67-0 ]
  • [ 129150-68-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5351 - 5381
  • 12
  • [ 51061-22-4 ]
  • [ 129150-68-1 ]
Reference: [1] Patent: WO2014/95920, 2014, A1,
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