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[ CAS No. 101166-65-8 ] {[proInfo.proName]}

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Chemical Structure| 101166-65-8
Chemical Structure| 101166-65-8
Structure of 101166-65-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 101166-65-8 ]

CAS No. :101166-65-8 MDL No. :MFCD09909940
Formula : C8H19IOSi Boiling Point : -
Linear Structure Formula :- InChI Key :CAAUZMMMFDVBFD-UHFFFAOYSA-N
M.W : 286.23 Pubchem ID :11129873
Synonyms :

Calculated chemistry of [ 101166-65-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 62.49
TPSA : 9.23 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) : -5.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.09
Log Po/w (XLOGP3) : 3.96
Log Po/w (WLOGP) : 3.44
Log Po/w (MLOGP) : 2.84
Log Po/w (SILICOS-IT) : 1.51
Consensus Log Po/w : 2.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.85
Solubility : 0.0409 mg/ml ; 0.000143 mol/l
Class : Soluble
Log S (Ali) : -3.85
Solubility : 0.04 mg/ml ; 0.00014 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.0983 mg/ml ; 0.000344 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.2

Safety of [ 101166-65-8 ]

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

Application In Synthesis of [ 101166-65-8 ]

* 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 [ 101166-65-8 ]
  • Downstream synthetic route of [ 101166-65-8 ]

[ 101166-65-8 ] Synthesis Path-Upstream   1~9

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YieldReaction ConditionsOperation in experiment
98% With 1H-imidazole In dichloromethane at 30℃; for 17 h; (i)
Preparation of (2-iodoethoxy)-tert-butyldimethylsilane
To a stirred solution of 2-iodoethanol (17.2 g; 100 mmol) and imidazole (8.17 g; 120 mmol) in dichloromethane (100 mL) was added tert-butyldimethylsilyl chloride (15.83 g; 105 mmol) at such a rate that the reaction temperature did not rise above 30° C.
Upon complete addition the solution was left stirring for 17 h, then washed with water (2*50 mL) and brine (50 mL) and dried over MgSO4.
Evaporation of the solvent afforded the target compound (28.0 g; 97.8 mmol; 98percent) as a colourless liquid.
1H-NMR (400 MHz) (CDCl3): δ=3.83 (t, 2H, J=7.0 Hz), 3.83 (t, 2H, J=7.0 Hz), 3.20 (t, 2H, J=7 Hz), 0.90 (s, 9H), 0.08 (s, 6H) ppm.
90% With 1H-imidazole In N,N-dimethyl-formamide at 30 - 40℃; for 4 h; Preparation of tert-butyl(2-iodoethoxy)dimethylsilane
After 2-iodoethanol (1.72 g, 10 mmol) was dissolved in dimethylformamide (8 mL), imidazole (0.817 g, 12 mmol) and tert-butyldimethylsilyl chloride (1.66 g, 11 mmol) were added thereto, and the mixture was stirred for 4 hours at 30° C. to 40° C. Water (50 mL) was added to the reaction solution, and the result was extracted with an ethyl acetate/normal-hexane=1/1 solution (100 mL).
The organic layer was washed again with salt water (30 mL*3), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.85 g (90percent) of a target compound.
This compound was used as it was for the next reaction without purification.
90% With 1H-imidazole In N,N-dimethyl-formamide at 30 - 40℃; for 4 h; Preparation of tert-butyl(2-iodoethoxy)dimethylsilane
After 2-iodoethanol (1.72 g, 10 mmol) was dissolved in dimethylformamide (8 mL), imidazole (0.817 g, 12 mmol) and tert-butyldimethylsilyl chloride (1.66 g, 11 mmol) were added thereto, and the mixture was stirred for 4 hours at 30°C to 40°C. Water (50 mL) was added to the reaction solution, and the result was extracted with an ethyl acetate/normal-hexane=1/1 solution (100 mL).
The organic layer was washed again with salt water (30 mLx3), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.85 g (90percent) of a target compound.
This compound was used as it was for the next reaction without purification.
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1157 - 1165
[2] Analytical Chemistry, 2003, vol. 75, # 21, p. 6002 - 6010
[3] Patent: US2013/59970, 2013, A1, . Location in patent: Paragraph 0311; 0312; 0313
[4] Patent: US2014/249162, 2014, A1, . Location in patent: Paragraph 0234
[5] Patent: EP2781519, 2014, A1, . Location in patent: Paragraph 0232
[6] Organic Letters, 2014, vol. 16, # 11, p. 2862 - 2864
[7] Organic Letters, 1999, vol. 1, # 3, p. 379 - 381
[8] Patent: US5939439, 1999, A,
[9] Patent: WO2013/152269, 2013, A1, . Location in patent: Page/Page column 83
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YieldReaction ConditionsOperation in experiment
100% With sodium iodide In acetone at 120℃; for 4 h; Inert atmosphere; Sealed tube; Microwave irradiation A solution of TBSCl (30.1 g, 200 mmol) in DCM (50 mL) was added dropwise over 15 min to a stirred solution of 2-chloroethanol (16.0 g, 200 mmol), imidazole (20.4 g, 300 mmol) and DMAP (0.244 g, 2.0 mmol) in DCM (200 mL) at 0 °C under an argon atmosphere, and the resulting mixture was warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (200 mL) and the separated aqueous layer was then washed with DCM (2*100 mL). The combined organic extracts were washed with saturated aqueous NH4Cl (100 mL) and brine (100 mL), then dried over MgSO4 and concentrated to leave 2-chloroethoxy tert-butyl dimethylsilane (37.1 g, 95percent) as a colourless oil. A solution of the silyl ether (3.88g, 20.0mmol) and sodium iodide (8.94g, 60 mmol) in acetone (10mL) was sealed in a microwave vial and heated at 120°C for 4h in a microwave reactor. The vial was cooled to room temperature and the reaction mixture was then diluted with diethyl ether (80mL) and filtered through silica. The filtrate was concentrated to leave 2-iodoethoxy tert-butyl dimethylsilane (5.72g, quant.) as a pale yellow oil, which was used without further purification. A solution of methyl acetoacetate (2.55g, 22.0mmol) in 79 THF (10mL) was added over 10 min to a stirred suspension of sodium hydride (0.88g, 22.0 mmol, 60percent) in THF (50mL) at 0°C under argon. The mixture was stirred for 15 min, and then a solution of n-butyl lithium (11.0 mL, 22.0 mmol, 2.0M in hexane) was added dropwise over 10 min and the mixture was stirred at 0°C for 15 min. A solution of the above, crude iodide (ca. 20 mmol) in THF (10 mL) was added dropwise over 10 min, and the resulting yellow mixture was then warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (100 mL) and diethyl ether (100mL), and the separated aqueous layer was then washed with diethyl ether (2×100mL). The combined organic extracts were washed with brine (100 mL), then dried over MgSO4 and concentrated to leave a pale yellow gum. Purification by column chromatography (25:1, petrol/Et2O) gave the keto ester (5.05 g, 77percent) as a pale yellow oil (10percent enol form): δH (400 MHz, CDCl3) 3.73 (3H, s, CO2CH3), 3.61 (2H, t, J=6.0, CH2O), 3.46 (2H, s, CH2), 2.62 (2H, t, J=7.1, CH2C(O)), 1.80 (2H, tt, J=6.0, 7.1, CH2), 0.87 (9H, s, SiC(CH3)3), 0.03 (6H, s, SiCH3); δC (100 MHz, CDCl3) 202.6 (C=O), 167.6 (CO2CH3), 61.8 (CH2O), 52.2 (CO2CH3), 49.0 (CH2), 39.4 (CH2), 26.5 (CH2), 25.9 (SiC(CH3)3), 18.2 (SiC(CH3)3), −5.4 (2×SiCH3); HRMS m/z C13H26O4SiNa+ (MNa+) requires 297.1498, found 297.1498.
Reference: [1] Tetrahedron, 2014, vol. 70, # 40, p. 7229 - 7240
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 1417 - 1424
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Reference: [1] Patent: US2001/34343, 2001, A1,
[2] Patent: US6423704, 2002, B1,
[3] Patent: US6194406, 2001, B1,
[4] Patent: WO2014/140241, 2014, A1, . Location in patent: Page/Page column 20; 38
[5] Helvetica Chimica Acta, 2016, vol. 99, # 7, p. 523 - 538
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Reference: [1] Patent: US2013/59926, 2013, A1, . Location in patent: Page/Page column
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Reference: [1] Synthesis, 1991, # 12, p. 1231 - 1235
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Reference: [1] Organic Letters, 2008, vol. 10, # 16, p. 3413 - 3415
[2] Journal of Organic Chemistry, 2011, vol. 76, # 8, p. 2408 - 2425
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  • [ 75-03-6 ]
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Reference: [1] Dalton Transactions, 2003, # 10, p. 2085 - 2092
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 1417 - 1424
[2] Journal of Organic Chemistry, 2011, vol. 76, # 8, p. 2408 - 2425
[3] Helvetica Chimica Acta, 2016, vol. 99, # 7, p. 523 - 538
[4] Tetrahedron, 2014, vol. 70, # 40, p. 7229 - 7240
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  • [ 590409-26-0 ]
  • [ 590409-43-1 ]
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Reference: [1] Patent: EP1477175, 2004, A1,
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