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[ CAS No. 86087-24-3 ] {[proInfo.proName]}

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Chemical Structure| 86087-24-3
Chemical Structure| 86087-24-3
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Product Details of [ 86087-24-3 ]

CAS No. :86087-24-3 MDL No. :MFCD00067101
Formula : C4H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XDPCNPCKDGQBAN-SCSAIBSYSA-N
M.W :88.11 Pubchem ID :641512
Synonyms :

Calculated chemistry of [ 86087-24-3 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 21.47
TPSA : 29.46 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) : -7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.35
Log Po/w (XLOGP3) : -0.41
Log Po/w (WLOGP) : -0.23
Log Po/w (MLOGP) : -0.57
Log Po/w (SILICOS-IT) : 0.84
Consensus Log Po/w : 0.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.13
Solubility : 65.6 mg/ml ; 0.745 mol/l
Class : Very soluble
Log S (Ali) : 0.26
Solubility : 159.0 mg/ml ; 1.8 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.18
Solubility : 133.0 mg/ml ; 1.51 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 86087-24-3 ]

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 [ 86087-24-3 ]

* 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 [ 86087-24-3 ]
  • Downstream synthetic route of [ 86087-24-3 ]

[ 86087-24-3 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 125605-10-9 ]
  • [ 86087-24-3 ]
YieldReaction ConditionsOperation in experiment
99.1% With hydrogenchloride; sodium hydroxide In methanol; water EXAMPLE 5
Preparation of (R)-3-Hydroxytetrahydrofuran
To 35 g (0.28 mol) of the (R)-4-chloro-1,3-butanediol obtained in Reference Example 2 hereinafter given was added 70 ml of 0.5N hydrochloric acid, followed by heating under reflux for 2 hours.
After cooling, the reaction mixture was neutralized with a 50percent aqueous solution of sodium hydroxide, and water was evaporated under reduced pressure.
To the residual mixture of crystals and an oily substance was added 60 ml of methanol, followed by stirring.
The crystals were removed by filtration, and the filtrate was concentrated under reduced pressure.
The residue was distilled under reduced pressure to give 16.6 g of the title compound as a colorless substance (purity: 99.1percent; yield: 67percent).
Optical rotation: [α]D23 =-15.91° (c=2.45, methanol)
88% for 16 h; Heating / reflux Example 4; [66] 800 mL of toluene was added to 218 g (1.758 mol) of (No.)-4-chloro-l,3-butanediol prepared in Example 3, and stirring was performed for 16 hours under reflux. The reaction mixture was cooled to room temperature and, after adding 37.3 g (0.352 mol) of Na2CO3 and 1 g (0.055 mol) of water, stirring was further performed for 30 minutes. After removing solid by filtering, the solvent was recovered by concentration under reduced pressure, and the residue was further distilled under reduced pressure. 137 g of colorless (/?)-3-hydroxytetrahydrofuran was obtained (yield = 88percent, overall yield = 85percent, optical purity = 99.52percent ee).
73.62 g for 2 h; Reflux Dilute hydrochloric acid (17.5 ml of conc. hydrochloric acid diluted with 332.50 ml of water) was added to (R)-4-chloro-1,3-butanediol (175 g) and stirring was performed for 2 hours under reflux. After completion of the reaction monitored by gas chromatography, the reaction mixture was cooled to 0 to 5°C followed by a pH adjustment between 7 to 8 by using aqueous sodium hydroxide solution (82.5 g of sodium hydroxide dissolved in 165 ml of water). The resulting reaction mass was diluted with methanol (525 ml) followed by distillation under reduced pressure maintaining temperature below 45°C. Water was completely removed using methanol stripping (2 x 525 ml) followed by addition of methyl tert-butyl ether (525 ml) to the concentrated mass. The resulting suspension was stirred for 30 minutes followed by filtration to remove inorganic materials. The solid cake was washed with methyl tert-butyl ether (100 ml) followed by distillation under reduced pressure maintaining temperature below 40°C to obtain a crude oil (88.46 g). The resulting crude material was distilled under reduced pressure at 90 to 95°C (5 mmHg pressure) to give pure (R)-tetrahydrofuran-3-ol as an oil (73.62 g, 59.47 percent).1H-NMR: (400 MHz, CDC13): ö: 4.44-4.45 (m, 1H), 3.90-3.97 (m, 1H), 3.69-3.80 (m, 2H), 3.02-3. 12 (brs, 1H), 2.00-2.08 (m, 1H), 1.84-2.00 (m, 1H)Mass [M+Hj: 88.81 Purity by GC: 99.43percent areaSpecific optical Rotation (C= 1, Methanol): -17.57°
Reference: [1] Patent: US5780649, 1998, A,
[2] Patent: WO2008/93955, 2008, A1, . Location in patent: Paragraph 65-66
[3] Patent: WO2016/21192, 2016, A1, . Location in patent: Paragraph 0085
  • 2
  • [ 70005-88-8 ]
  • [ 86087-24-3 ]
YieldReaction ConditionsOperation in experiment
99% at 100℃; Example 4; 5 g of the catalyst used in Example 1 was loaded into a completely automated continuous fixed-bed reactor made of 316 stainless steel, after which the internal temperature of the reactor was adjusted to 100°C and then a dioxane solution containing 10 wtpercent of (R)- 1,2,4- butanetriol (optical purity of 99.0percent) was fed into the reactor at a WHSV of 2.0 h~ to thus <n="8"/>conduct the reaction.The results of the preparation of (R)-3-tetrahydrofuran are shown in Table 3 below.
Reference: [1] Patent: WO2007/81065, 2007, A1, . Location in patent: Page/Page column 6-7
[2] Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2767 - 2769
  • 3
  • [ 42890-76-6 ]
  • [ 106-97-8 ]
  • [ 86087-24-3 ]
YieldReaction ConditionsOperation in experiment
54% With CH3SO3H In water EXAMPLE 4
Preparation of (R)-3-hydroxytetrahydrofuran
To a mixture of (S)-1,2,4-trimesyloxy butane (10 g), prepared as in HETEROCYCLES vol.24 N° 5, 1986 p.1331, starting from (S)-1,2,4-butanetriol having e.e. >99percent, in H2O (200 ml) CH3SO3H (5.6g) is added.
The temperature is left to rise up to 80° C. and kept for 27h.
After cooling to r.t. the mixture is treated in batch with IRA 410 (OH-form) (0.2 L).
The resin is filtered off, and washed with H2O; the filtrate gives, after distillation and chromatographic purification (R)-3-hydroxytetrahydrofuran with 94percent e.e. (yield 54percent).
Reference: [1] Patent: US2003/32818, 2003, A1,
  • 4
  • [ 1358604-08-6 ]
  • [ 86087-24-3 ]
Reference: [1] Patent: WO2017/130217, 2017, A1, . Location in patent: Page/Page column 22; 35
  • 5
  • [ 27999-96-8 ]
  • [ 86087-24-3 ]
Reference: [1] Patent: CN106957287, 2017, A, . Location in patent: Paragraph 0042
  • 6
  • [ 778-29-0 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Tetrahedron Asymmetry, 2012, vol. 23, # 11-12, p. 898 - 903
  • 7
  • [ 453-20-3 ]
  • [ 108-05-4 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Tetrahedron Asymmetry, 2012, vol. 23, # 8, p. 583 - 586
  • 8
  • [ 22929-52-8 ]
  • [ 86087-24-3 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 3, p. 1598 - 1605
[2] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246
  • 9
  • [ 22929-52-8 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246
[2] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246
  • 10
  • [ 453-20-3 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Tetrahedron Asymmetry, 2000, vol. 11, # 23, p. 4781 - 4790
  • 11
  • [ 27999-96-8 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2001, vol. 40, # 22, p. 4201 - 4204
  • 12
  • [ 27999-96-8 ]
  • [ 86087-24-3 ]
Reference: [1] FEBS Journal, 2013, vol. 280, # 13, p. 3084 - 3093
  • 13
  • [ 1191-99-7 ]
  • [ 86087-24-3 ]
Reference: [1] Heterocycles, 1989, vol. 28, # 1, p. 283 - 294
[2] Journal of the American Chemical Society, 1986, vol. 108, # 8, p. 2049 - 2054
  • 14
  • [ 1708-29-8 ]
  • [ 86087-24-3 ]
Reference: [1] Journal of the American Chemical Society, 1986, vol. 108, # 8, p. 2049 - 2054
  • 15
  • [ 145873-44-5 ]
  • [ 1708-29-8 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Liebigs Annales, 1997, # 9, p. 1877 - 1879
[2] Liebigs Annales, 1997, # 9, p. 1877 - 1879
  • 16
  • [ 778-29-0 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Tetrahedron Asymmetry, 2012, vol. 23, # 11-12, p. 898 - 903
  • 17
  • [ 453-20-3 ]
  • [ 108-05-4 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Tetrahedron Asymmetry, 2012, vol. 23, # 8, p. 583 - 586
  • 18
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 7, p. 931 - 935
  • 19
  • [ 22929-52-8 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246
[2] ChemBioChem, 2018, vol. 19, # 3, p. 239 - 246
  • 20
  • [ 453-20-3 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Tetrahedron Asymmetry, 2000, vol. 11, # 23, p. 4781 - 4790
  • 21
  • [ 27999-96-8 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2001, vol. 40, # 22, p. 4201 - 4204
  • 22
  • [ 145873-44-5 ]
  • [ 1708-29-8 ]
  • [ 86087-24-3 ]
  • [ 86087-23-2 ]
Reference: [1] Liebigs Annales, 1997, # 9, p. 1877 - 1879
[2] Liebigs Annales, 1997, # 9, p. 1877 - 1879
  • 23
  • [ 864070-18-8 ]
  • [ 86087-24-3 ]
  • [ 915095-89-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 10, p. 4173 - 4184
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