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[ CAS No. 23601-40-3 ] {[proInfo.proName]}

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Chemical Structure| 23601-40-3
Chemical Structure| 23601-40-3
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Product Details of [ 23601-40-3 ]

CAS No. :23601-40-3 MDL No. :MFCD00045996
Formula : C13H28O7 Boiling Point : -
Linear Structure Formula :- InChI Key :FHHGCKHKTAJLOM-UHFFFAOYSA-N
M.W :296.36 Pubchem ID :90207
Synonyms :
Hexaethylene glycol monomethyl ether

Calculated chemistry of [ 23601-40-3 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 17
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.28
TPSA : 75.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.76
Log Po/w (XLOGP3) : -1.34
Log Po/w (WLOGP) : -0.29
Log Po/w (MLOGP) : -1.42
Log Po/w (SILICOS-IT) : 1.92
Consensus Log Po/w : 0.53

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.29
Solubility : 576.0 mg/ml ; 1.94 mol/l
Class : Highly soluble
Log S (Ali) : 0.25
Solubility : 529.0 mg/ml ; 1.78 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.98
Solubility : 0.307 mg/ml ; 0.00104 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 23601-40-3 ]

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 [ 23601-40-3 ]

* 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 [ 23601-40-3 ]
  • Downstream synthetic route of [ 23601-40-3 ]

[ 23601-40-3 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 62921-74-8 ]
  • [ 112-27-6 ]
  • [ 23601-40-3 ]
YieldReaction ConditionsOperation in experiment
69% at 100℃; for 12 h; 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (Al, 1.0 g, 3.14 mmol) was added with stir to triethylene glycol (2.10 mL, 15.7 mmol). Potassium hydroxide (510 mg, 9.42 mmol) was ground into a powder and added to the reaction and the mixture refluxed at 100°C for 12 hours, upon which the reaction was diluted with water (50 mL) and extracted with DCM. The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure to obtain 2,5,8,1 l,14,17-hexaoxanonadecan-19-ol as a yellow oil in 69percent yield.
65% Reflux The synthesis of compound 3 is shown in Figure 5. Synthesis of compound 3 began by coupling tosylate (6) to triethylene glycol (16) under basic conditions to yield hexaethylene glycol monomethyl ether (17) in 65percent yield. Hexaethylene glycol monomethyl ether (17) was then converted to the corresponding tosylate (18) in 77percent yield, followed by conversion to the azide. The azide was reduced to the corresponding amine (19) via a hydrogenation over activated palladium on carbon in 45percent yield. The amine was coupled to cyanoacetic acid using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in 80percent yield to give the cyano-acetamide (20). The resulting amide (20) was coupled with previously synthesized piperidine-naphthalene (12) to give compound 3 via Knovenagel condensation in 61percent yield.
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 20, p. 7499 - 7508
[2] Organic Letters, 2004, vol. 6, # 4, p. 469 - 472
[3] Patent: WO2015/143185, 2015, A1, . Location in patent: Paragraph 00819
[4] Patent: WO2016/40891, 2016, A2, . Location in patent: Paragraph 00316
[5] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 7, p. 2193 - 2198
  • 2
  • [ 125562-28-9 ]
  • [ 23601-40-3 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In tetrahydrofuran for 1.5 h; D. Hexaethylene Glycol Monomethvl Ether A 50percent wet paste of 10percent palladium on carbon (0.71 g, 5 molpercent) was charged to a nitrogen purged flask. A solution of hexaethylene glycol monomethyl monobenzyl ether ("BnO-6EG-OMe"; 2.66g, 6.88 mmol) in tetrahydrofuran (26.6 mL) was added. The mixture was stirred under an atmosphere of hydrogen for 90 minutes. The mixture was filtered through celite to remove the catalyst. The solids were washed with tetrahydrofuran (20 mL). The filtrate was concentrated to dryness to give hexaethylene glycol monomethyl ether (2.01 g, 99percent theory). 1H NMR (250 MHz, CDCl3, S44238) No.H (CDCl3, ppm from TMS) 3.8-3.5 (24 H, m, CH2 x 12), 3.38 (3 H, s, OCH3), 2.08 (1 H, brs, OH).
Reference: [1] Patent: WO2005/102976, 2005, A1, . Location in patent: Page/Page column 9-10
  • 3
  • [ 111-77-3 ]
  • [ 23601-40-3 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 12 h; Inert atmosphere
Stage #3: With sulfuric acid; water In tetrahydrofuran for 3 h; Inert atmosphere; Reflux
(Using the synthesis of M-PEG 7 as an example). Under the atmosphere of N2, to a suspension of NaH (1.0 g, 60percent dispersed in mineral oil, 25.0 mmol) in THF (60 mL) at 0 was added a solution of M-PEG 5 (2.0 g, 16.6 mmol) in THF (20 mL). After the addition, the stirring mixture was warmed to rt and stirred for 30 min. Then, a solution of macrocyclic sulfate 8 (5.1 g, 20.0 mmol) in THF (20 mL) was added. The resulting mixture was stirred for 12 h at rt, and concentrated under vacuum. The resulting residue was dissolved in water (50 mL), and washed with CH2Cl2. The aqueous layer was concentrated and then dissolved in THF (100 mL). Then, water (0.6 mL, 33.3 mmol) and H2SO4 (0.4 mL, 8.4 mmol) were added to the reaction mixture and the resulting mixture was refluxed for 3 h. The reaction was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4, concentrated under vacuum, and purified by flash chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give M-OEG 7 as clear oil (4.3 g, 88percent yield). 1H NMR (400 MHz, CDCl3) δ 3.73-3.70 (m, 2H), 3.70-3.63 (m, 18H), 3.62-3.59 (m, 2H), 3.57-3.55 (m, 2H), 3.39 (s, 3H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 22, p. 3502 - 3505
  • 4
  • [ 2615-15-8 ]
  • [ 74-88-4 ]
  • [ 23601-40-3 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5682 - 5685
[2] Journal of Organometallic Chemistry, 2005, vol. 690, # 24-25, p. 5581 - 5590
[3] Chemical Communications, 2006, # 32, p. 3438 - 3440
[4] Journal of the American Chemical Society, 1995, vol. 117, # 23, p. 6249 - 6253
[5] European Journal of Organic Chemistry, 2008, # 19, p. 3308 - 3313
[6] Dalton Transactions, 2012, vol. 41, # 9, p. 2738 - 2746
  • 5
  • [ 1134159-69-5 ]
  • [ 23601-40-3 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 2, p. 452 - 458
[2] Journal of Organic Chemistry, 2011, vol. 76, # 3, p. 875 - 881
  • 6
  • [ 75-44-5 ]
  • [ 6066-82-6 ]
  • [ 2615-15-8 ]
  • [ 23601-40-3 ]
Reference: [1] Patent: US2003/27748, 2003, A1,
[2] Patent: US2003/60606, 2003, A1,
  • 7
  • [ 112-35-6 ]
  • [ 23601-40-3 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 20, p. 7499 - 7508
[2] Organic Letters, 2004, vol. 6, # 4, p. 469 - 472
[3] Chemistry - An Asian Journal, 2011, vol. 6, # 2, p. 452 - 458
[4] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 7, p. 2193 - 2198
[5] Patent: WO2015/143185, 2015, A1,
[6] Patent: WO2016/40891, 2016, A2,
[7] Patent: US2858315, 1957, ,
  • 8
  • [ 112-35-6 ]
  • [ 112-27-6 ]
  • [ 23601-40-3 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 160, p. 331 - 338
  • 9
  • [ 67-56-1 ]
  • [ 2615-15-8 ]
  • [ 74-88-4 ]
  • [ 23601-40-3 ]
Reference: [1] Patent: US5606038, 1997, A,
  • 10
  • [ 74654-05-0 ]
  • [ 112-27-6 ]
  • [ 23601-40-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 24, p. 10295 - 10300
  • 11
  • [ 2615-15-8 ]
  • [ 77-78-1 ]
  • [ 23601-40-3 ]
Reference: [1] New Journal of Chemistry, 2008, vol. 32, # 7, p. 1140 - 1152
  • 12
  • [ 62921-74-8 ]
  • [ 23601-40-3 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 2, p. 452 - 458
  • 13
  • [ 60221-37-6 ]
  • [ 23601-40-3 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 2, p. 452 - 458
  • 14
  • [ 112-27-6 ]
  • [ 23601-40-3 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 2, p. 452 - 458
  • 15
  • [ 111-77-3 ]
  • [ 23601-40-3 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 9, p. 1357 - 1360
  • 16
  • [ 5197-62-6 ]
  • [ 23601-40-3 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 3, p. 875 - 881
  • 17
  • [ 85539-28-2 ]
  • [ 23601-40-3 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 3, p. 875 - 881
  • 18
  • [ 112-60-7 ]
  • [ 23601-40-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 22, p. 3502 - 3505
  • 19
  • [ 112-60-7 ]
  • [ 50586-80-6 ]
  • [ 23601-40-3 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 9, p. 1357 - 1360
  • 20
  • [ 75-21-8 ]
  • [ 109-86-4 ]
  • [ 23601-40-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1973, vol. 46, p. 623 - 626
  • 21
  • [ 52995-76-3 ]
  • [ 112-27-6 ]
  • [ 23601-40-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1978, vol. 51, p. 3111 - 3120
  • 22
  • [ 23601-40-3 ]
  • [ 27425-92-9 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 12 h; Inert atmosphere
Stage #3: With sulfuric acid; water In tetrahydrofuran for 3 h; Inert atmosphere; Reflux
General procedure: (Using the synthesis of M-PEG 7 as an example). Under the atmosphere of N2, to a suspension of NaH (1.0 g, 60percent dispersed in mineral oil, 25.0 mmol) in THF (60 mL) at 0 was added a solution of M-PEG 5 (2.0 g, 16.6 mmol) in THF (20 mL). After the addition, the stirring mixture was warmed to rt and stirred for 30 min. Then, a solution of macrocyclic sulfate 8 (5.1 g, 20.0 mmol) in THF (20 mL) was added. The resulting mixture was stirred for 12 h at rt, and concentrated under vacuum. The resulting residue was dissolved in water (50 mL), and washed with CH2Cl2. The aqueous layer was concentrated and then dissolved in THF (100 mL). Then, water (0.6 mL, 33.3 mmol) and H2SO4 (0.4 mL, 8.4 mmol) were added to the reaction mixture and the resulting mixture was refluxed for 3 h. The reaction was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4, concentrated under vacuum, and purified by flash chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give M-OEG 7 as clear oil (4.3 g, 88percent yield).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 22, p. 3502 - 3505
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