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[ CAS No. 1611-56-9 ] {[proInfo.proName]}

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Chemical Structure| 1611-56-9
Chemical Structure| 1611-56-9
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Product Details of [ 1611-56-9 ]

CAS No. :1611-56-9 MDL No. :MFCD00004752
Formula : C11H23BrO Boiling Point : -
Linear Structure Formula :- InChI Key :XFGANBYCJWQYBI-UHFFFAOYSA-N
M.W : 251.20 Pubchem ID :74163
Synonyms :

Calculated chemistry of [ 1611-56-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 10
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 64.02
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.4
Log Po/w (XLOGP3) : 4.71
Log Po/w (WLOGP) : 3.88
Log Po/w (MLOGP) : 3.55
Log Po/w (SILICOS-IT) : 4.07
Consensus Log Po/w : 3.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0496 mg/ml ; 0.000197 mol/l
Class : Soluble
Log S (Ali) : -4.86
Solubility : 0.00344 mg/ml ; 0.0000137 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.62
Solubility : 0.0061 mg/ml ; 0.0000243 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.08

Safety of [ 1611-56-9 ]

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 [ 1611-56-9 ]

* 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 [ 1611-56-9 ]
  • Downstream synthetic route of [ 1611-56-9 ]

[ 1611-56-9 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 6287-90-7 ]
  • [ 1611-56-9 ]
YieldReaction ConditionsOperation in experiment
98.9% With hydrogenchloride In diethylene glycol dimethyl ether; water (2)
Sodium Borohydride (16.32 g, 0.43 mole) was dissolved in diglyme (350 ml).
To this was added a solution of aluminium trichloride (19.2 g, 0.14 mole) in diglyme (250 ml) maintaining the temperature below 20°.
After the addition was complete, the mixture was stirred for 0.5 hour at room temperature.
The reducing agent was then added dropwise to a solution of methyl 11-bromoundecanoate* (120 g, 0.43 mole) in diglyme (200 ml) maintaining the temperature at 10°.
After the addition was complete the reaction was stirred at 20° for 3 hours and then quenched by pouring onto water (2 L) and concentrated HCl (100 ml).
The quenched mixture was stirred for 1 hour then cooled to 15°.
The product was filtered off, washed with water (2*500 ml) and dried under vacuum to give 11-bromoundecanol (106.8 g, 98.9percent).
* This methyl ester can be produced in quantitative yield by esterifying 11-bromoundecanoic acid with MeOH/H2 SO4
Reference: [1] Patent: US5441731, 1995, A,
  • 2
  • [ 6287-90-7 ]
  • [ 1611-56-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 2, p. 455 - 461
[2] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 248 - 251[3] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 2, p. 279 - 282
[4] Tetrahedron, 2009, vol. 65, # 20, p. 3961 - 3966
[5] Journal of the American Chemical Society, 1975, vol. 97, # 9, p. 2488 - 2496
  • 3
  • [ 2834-05-1 ]
  • [ 1611-56-9 ]
YieldReaction ConditionsOperation in experiment
99.2% With hydrogenchloride In tetrahydrofuran; diethylene glycol dimethyl ether; water (i)
Sodium Borohydride (28.8 g, 0.76 mole) was dissolved in diglyme (700 ml) and THF (300 ml) and the solution cooled to 20° (dissolution of the NaBH4 is slightly exothermic). BF3 OEt2 (145 g, 1.02 mole) was then added dropwise, with external cooling, at such a rate to keep the temperature of the mixture below 15°.
After the addition was complete the mixture was stirred for 0.5 hour at 10°.
This reducing agent was then added slowly to a solution of 11-bromoundecanoic acid (200 g, 0.76 mole) in THF (400 ml) keeping the temperature below 20°.
After the addition was complete, the reaction was stirred at room temperature for 1.5 hours then quenched by pouring onto water (3 L) and concentrated HCl (100 ml).
The quenched mixture was stirred for 0.5 hour at room temperature then cooled to 5°.
The crystalline product was filtered off, washed with water (3*1 L) and dried under vacuum to give 11-bromoundecanol (189.2 g, 99.2percent).
Reference: [1] Patent: US5441731, 1995, A,
  • 4
  • [ 2834-05-1 ]
  • [ 109-63-7 ]
  • [ 1611-56-9 ]
Reference: [1] Patent: US3978140, 1976, A,
  • 5
  • [ 2834-05-1 ]
  • [ 1611-56-9 ]
Reference: [1] Chemistry of Natural Compounds, 2008, vol. 44, # 2, p. 224 - 226
[2] Monatshefte fuer Chemie, 1989, vol. 120, p. 967 - 972
[3] Journal of Organic Chemistry, 1970, vol. 35, p. 4241 - 4244
[4] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6638 - 6640
[5] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 248 - 251[6] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 2, p. 279 - 282
[7] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 2, p. 455 - 461
[8] Journal of the American Chemical Society, 1975, vol. 97, # 9, p. 2488 - 2496
  • 6
  • [ 765-04-8 ]
  • [ 1611-56-9 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 4976
[2] Journal of the American Chemical Society, 1988, vol. 110, p. 8117
[3] Helvetica Chimica Acta, 1987, vol. 70, p. 822 - 861
[4] Chemistry Letters, 1994, # 10, p. 1789 - 1792
[5] Journal of Physical Chemistry, 1996, vol. 100, # 28, p. 18852 - 18858
[6] Journal of Chemical Ecology, 1994, vol. 20, # 12, p. 3029 - 3037
[7] Molecules, 2012, vol. 17, # 7, p. 8217 - 8240
  • 7
  • [ 19779-06-7 ]
  • [ 1611-56-9 ]
Reference: [1] Patent: US4444766, 1984, A,
  • 8
  • [ 70326-40-8 ]
  • [ 1611-56-9 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7022 - 7025
  • 9
  • [ 6287-90-7 ]
  • [ 112-42-5 ]
  • [ 1611-56-9 ]
Reference: [1] Synthetic Communications, 1996, vol. 26, # 6, p. 1143 - 1147
  • 10
  • [ 101686-44-6 ]
  • [ 1611-56-9 ]
Reference: [1] Synthesis, 2006, # 18, p. 3085 - 3091
  • 11
  • [ 112-19-6 ]
  • [ 1611-56-9 ]
Reference: [1] Journal of Organic Chemistry, 1956, vol. 21, p. 739,743,746[2] Journal of the American Chemical Society, 1956, vol. 78, p. 3484,3485
[3] Journal of Organic Chemistry, 1953, vol. 18, p. 1356,1361
  • 12
  • [ 13688-67-0 ]
  • [ 1611-56-9 ]
Reference: [1] Journal of Physical Chemistry, 1996, vol. 100, # 28, p. 18852 - 18858
  • 13
  • [ 53463-68-6 ]
  • [ 1611-56-9 ]
Reference: [1] Helvetica Chimica Acta, 1987, vol. 70, p. 822 - 861
  • 14
  • [ 4850-47-9 ]
  • [ 1611-56-9 ]
Reference: [1] Helvetica Chimica Acta, 1987, vol. 70, p. 822 - 861
  • 15
  • [ 112-46-9 ]
  • [ 1611-56-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1953, vol. 72, p. 411,415
  • 16
  • [ 15949-84-5 ]
  • [ 1611-56-9 ]
Reference: [1] Acta Crystallographica, Section B: Structural Crystallography and Crystal Chemistry, 1972, vol. 28, p. 610,615
  • 17
  • [ 6271-23-4 ]
  • [ 1611-56-9 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 2217
  • 18
  • [ 7766-50-9 ]
  • [ 1611-56-9 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 40, p. 6015 - 6016
  • 19
  • [ 1611-56-9 ]
  • [ 2834-05-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 19, p. 5856 - 5860[2] Angew. Chem., 2016, vol. 128, # 19, p. 5950 - 5955,6
[3] Organic Letters, 2012, vol. 14, # 1, p. 350 - 353
[4] Journal of Physical Chemistry, 1996, vol. 100, # 28, p. 18852 - 18858
  • 20
  • [ 1611-56-9 ]
  • [ 557-61-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 2, p. 604 - 608
  • 21
  • [ 1611-56-9 ]
  • [ 73768-94-2 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 1, p. 157 - 162
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 8, p. 1115 - 1125
[3] Patent: US6362352, 2002, B1, . Location in patent: Example 3
[4] Canadian Journal of Chemistry, 2012, vol. 90, # 1, p. 145 - 152
  • 22
  • [ 1611-56-9 ]
  • [ 18107-18-1 ]
  • [ 99828-63-4 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 1, p. 41 - 44
  • 23
  • [ 1611-56-9 ]
  • [ 99828-63-4 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 26, p. 4481 - 4483
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