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[ CAS No. 82769-75-3 ] {[proInfo.proName]}

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Chemical Structure| 82769-75-3
Chemical Structure| 82769-75-3
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Product Details of [ 82769-75-3 ]

CAS No. :82769-75-3 MDL No. :MFCD09955476
Formula : C11H17NO Boiling Point : -
Linear Structure Formula :- InChI Key :LPTVKPNWVGBWSU-NSHDSACASA-N
M.W : 179.26 Pubchem ID :12520912
Synonyms :

Calculated chemistry of [ 82769-75-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.69
TPSA : 23.47 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) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.24
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.35
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 1.66
Consensus Log Po/w : 1.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.99 mg/ml ; 0.0111 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 4.83 mg/ml ; 0.0269 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.79
Solubility : 0.291 mg/ml ; 0.00163 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 82769-75-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 82769-75-3 ]

* 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 [ 82769-75-3 ]
  • Downstream synthetic route of [ 82769-75-3 ]

[ 82769-75-3 ] Synthesis Path-Upstream   1~15

  • 1
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YieldReaction ConditionsOperation in experiment
93.02% for 8 h; Reflux; Large scale A solution of the above-prepared 3-amino-3-phenylpropanol (1.5 kg)Was dissolved in 1.6 kg (88percent, 30 mol) of formic acid,Add 2.8kg (37percent, 35mo 1) formaldehyde solution, heated to reflux, the reaction 8h.The reaction was quenched, concentrated under reduced pressure, 2L7K was added, adjusted to pH 12 with 10percent aqueous sodium hydroxide solution, and extracted with 3L / 4 times ethyl acetate. Combined with ethyl acetateThe layers were washed twice with 6 L saturated brine. Dried and concentrated under reduced pressure to give 1.65 kg of (s) -3-dimethylamino-3-phenylpropanol, purity (HPLC): 97.36percent yield 93.02percent. Ethyl acetate recovery cycle.
80% With sodium cyanoborohydride; acetic acid In acetonitrile at 20℃; for 2 h; To a solution of (XIII) (0.12 g, 0.807 mmol) in acetonitrile was added, 30percent aq formaldehyde solution (0.325 mL) followed by sodium cyanoborohydride (0.081 g, 1.29 mmol) and it was allowed to stir at room temperature. A few drops of glacial acetic acid were added to maintain the pH near neutrality. The solution was stirred at room temperature for 2 h. After completion of the reaction (TLC), the reaction mixture was concentrated in vacuo. To the residue was added 2 N aq KOH (10 mL). It was then extracted with ethyl acetate (3x10 mL). The ethyl acetate layer was then washed with 1 N HCl (3x5 mL). The combined HCl extracts were basified with solid KOH and then extracted with ethyl acetate (3x10 mL). Combined organic extracts were washed with brine (10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to afford crude product, which was purified by column chromatography (40percent EtOAc/MeOH) to furnish 15 (0.115 g, 80percent) as a hygroscopic solid.
Reference: [1] Patent: CN106883133, 2017, A, . Location in patent: Paragraph 0048-0049; 0095; 0097
[2] Tetrahedron Asymmetry, 2007, vol. 18, # 17, p. 2099 - 2103
[3] Tetrahedron Asymmetry, 2006, vol. 17, # 5, p. 860 - 866
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 12, p. 2543 - 2548
[5] Tetrahedron, 2009, vol. 65, # 12, p. 2605 - 2609
[6] Patent: EP2749553, 2014, A1, . Location in patent: Paragraph 0104; 0105
[7] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 395 - 406
  • 2
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YieldReaction ConditionsOperation in experiment
90.7%
Stage #1: With sodium tetrahydroborate In tetrahydrofuran
Stage #2: With methanesulfonic acid In tetrahydrofuran at 30℃;
Stage #3: With sodium hydroxide In tetrahydrofuran; water
Example-15: Preparation of (+)-3-N,N-dimethyl amino-3-phenyI propanol; Same procedure as described in Ex. 1 but using 50 g. of (+)-3-N,N-dimethyl amino-3- phenyl propanoic acid, 750 ml of tetrahydrofuran (THF), 24.5 g. of sodium borohydride and 64 g. of methane sulfonic acid to provide the title compound.Wt: 40-42gr. (percentYield: 90.7percent); Purity by HPLC: 98percent; SOR: +44.4° (0.6percent CHCI3).
Reference: [1] Patent: WO2011/161690, 2011, A1, . Location in patent: Page/Page column 25
  • 3
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Reference: [1] Patent: WO2011/161690, 2011, A1, . Location in patent: Page/Page column 27
  • 4
  • [ 82769-77-5 ]
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Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 4004 - 4005
  • 5
  • [ 85608-26-0 ]
  • [ 82769-75-3 ]
YieldReaction ConditionsOperation in experiment
82.26%
Stage #1: With sodium tetrahydroborate In tetrahydrofuran
Stage #2: With methanesulfonic acid In tetrahydrofuran at 30℃;
Stage #3: With sodium hydroxide In tetrahydrofuran; water
Example -17: Preparation of (+)-3-N,N-dimethyl amino-3-phenyl propanol; Same procedure as described in Ex. 1 but using 50 g. of (+)-3-N,N-dimethyl amino-3- phenyl propanoic acid hydrochloride, 750 ml of tetrahydrofuran (THF), 24.6 g. of sodium borohydride and 87.08 g. of methane sulfonic acid to provide the title compound.Wt: 30-32gr. (percentYield: 82.26percent); SOR : (+) 43.56°(0.6percent in CHC13); Purity by HPLC: 98percent.
Reference: [1] Patent: WO2011/161690, 2011, A1, . Location in patent: Page/Page column 26
  • 6
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YieldReaction ConditionsOperation in experiment
99.6% for 6 h; Reflux In a reaction flask was added 500ml three intermediate II 44.25g (0.25mol) were added successively 111.2 g of 88percent formic acid, 111.2 g of water, followed by addition of paraformaldehyde (1.0 mol), refluxed for 6h, cooled to room temperature, add 50percent sodium hydroxide to adjust to pH 13, extracted with ethyl acetate 140ml × 3, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a yellow oil 3-dimethylaminopropyl-3-phenylpropionate alcohol (III) 44.61g, yield 99.6percent.
Reference: [1] Patent: CN105061230, 2017, B, . Location in patent: Paragraph 0067; 0068; 0069
  • 7
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  • [ 82769-74-2 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 4004 - 4005
  • 8
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Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 395 - 406
  • 9
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Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 4004 - 4005
  • 10
  • [ 82769-79-7 ]
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Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 4004 - 4005
  • 11
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Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 20, p. 4004 - 4005
  • 12
  • [ 81402-52-0 ]
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Reference: [1] Patent: WO2011/161690, 2011, A1,
[2] Patent: WO2011/161690, 2011, A1,
  • 13
  • [ 85608-26-0 ]
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Reference: [1] Patent: WO2011/161690, 2011, A1,
[2] Patent: WO2011/161690, 2011, A1,
  • 14
  • [ 6098-50-6 ]
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Reference: [1] Patent: WO2011/161690, 2011, A1,
[2] Patent: WO2011/161690, 2011, A1,
  • 15
  • [ 82769-74-2 ]
  • [ 82769-75-3 ]
Reference: [1] Patent: WO2011/161690, 2011, A1,
[2] Patent: WO2011/161690, 2011, A1,
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