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[ CAS No. 6089-09-4 ] {[proInfo.proName]}

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Chemical Structure| 6089-09-4
Chemical Structure| 6089-09-4
Structure of 6089-09-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6089-09-4 ]

CAS No. :6089-09-4 MDL No. :MFCD00004407
Formula : C5H6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MLBYLEUJXUBIJJ-UHFFFAOYSA-N
M.W : 98.10 Pubchem ID :22464
Synonyms :
Propargylacetic acid

Calculated chemistry of [ 6089-09-4 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 26.08
TPSA : 37.3 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) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 0.3
Log Po/w (WLOGP) : 0.56
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 0.35
Consensus Log Po/w : 0.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.51
Solubility : 30.7 mg/ml ; 0.312 mol/l
Class : Very soluble
Log S (Ali) : -0.65
Solubility : 22.2 mg/ml ; 0.226 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.06
Solubility : 84.7 mg/ml ; 0.863 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 6089-09-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6089-09-4 ]

* 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 [ 6089-09-4 ]
  • Downstream synthetic route of [ 6089-09-4 ]

[ 6089-09-4 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 5390-04-5 ]
  • [ 6089-09-4 ]
YieldReaction ConditionsOperation in experiment
82% With Jones reagent In acetone at 0 - 20℃; for 1 h; 23d (lmL, 10.7 mmol) was dissolved in Acetone and cooled to 0°C. Jones reagent was added dropwise to the solution, under vigorous stirring, until the reaction mixture remained orange. The mixture was allowed to reach r.t., and more Jones reagent wasadded to maintain the orange colour. The reaction mixture was stirred at r.t. for lh, then water was added, and was extracted with Et20 several times, washed with Brine and dried over anhydrous Na2504. The solvent was removed at reduced pressure and the resulting oil purified by flash chromatography on silica gel (Hexane/Et20 8:2). Yield 82percent, colourless oil. 1HNMR (400 MHz CDC13-d): ö 2.61-2.59 (m, 2H), 2.52-2.48 (m, 2H), 1.98-1.95 (m, 1H) ppm.
82% With Jones reagent In acetone at 0 - 20℃; for 1 h; 23d (lmL, 10.7 mmol) was dissolved in Acetone and cooled to 0°C. Jones reagent was added dropwise to the solution, under vigorous stirring, until the reaction mixture remained orange. The mixture was allowed to reach r.t., and more Jones reagent was added to maintain the orange colour. The reaction mixture was stirred at r.t. for 1 h, then water was added, and was extracted with Et20 several times, washed with Brine and dried over anhydrous Na2SO4. The solvent was removed at reduced pressure and the resulting oil purified by flash chromatography on silica gel (Hexane/Et20 8:2). Yield 82percent, colourless oil. 1HNMR (400 MHz CDC13-d): ö 2.61-2.59 (m, 2H), 2.52-2.48 (m, 2H), 1.98-1.95 (m, 1H) ppm.
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2600 - 2603
[2] Patent: WO2016/128541, 2016, A1, . Location in patent: Page/Page column 53
[3] Patent: WO2017/162834, 2017, A1, . Location in patent: Page/Page column 45
[4] Tetrahedron, 2009, vol. 65, # 24, p. 4664 - 4670
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 2976 - 2979
[6] Journal of the American Chemical Society, 1988, vol. 110, # 22, p. 7419 - 7434
[7] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8344 - 8347
[8] Chemistry - A European Journal, 2014, vol. 20, # 46, p. 15131 - 15143
[9] Journal of the Chemical Society, 1953, p. 3052,3055
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 1981 - 1987
[11] Synthetic Communications, 1974, vol. 4, p. 203 - 210
[12] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 582 - 587
[13] Organic Mass Spectrometry, 1989, vol. 24, p. 909 - 916
[14] Journal of Chemical Research, Miniprint, 1995, # 11, p. 2642 - 2657
[15] Tetrahedron Letters, 2012, vol. 53, # 14, p. 1695 - 1698
[16] ChemPlusChem, 2016, vol. 81, # 11, p. 1160 - 1165
[17] Patent: WO2018/132326, 2018, A1, . Location in patent: Page/Page column 20
  • 2
  • [ 24342-04-9 ]
  • [ 6089-09-4 ]
YieldReaction ConditionsOperation in experiment
51% With copper(I) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 4-Pentynoic acid, 5-(2,5-dimethoxy-4-methylphenyl)-, methyl ester (4.2)
To 3.88 g. (14.0 mmol) of the aryl iodide 4.1 and 1.88 g methyl pentynoate (16.7 mmol) in 50 mL of dry DMF was added 0.277 g. (1.45 mmol) of cuprous iodide and 0.80 g. (0.69 mmol) of tetrakis (triphenylphosphine palladium (0) (Lancaster).
The flask was flushed with argon and sealed with a septum, and 3.6 mL of N,N-diisopropylethylamine was added to the flask.
After stirring overnight, TLC showed a trace of unreacted starting material.
The solution was evaporated and the residue was purified by flash chromatography (5*40 cm silica) using a gradient of 1:1 hexanes-methylene chloride to 100percent methylene chloride.
Evaporation gave a dark brown solid.
Despite good NMR purity, a second silica gel column was run using an eluent of 4:1 hexanes-ethyl acetate to eliminate color.
Appropriate fractions were collected and evaporated to give 1.88 g (51percent yield) of the desired product 4.2 as an off-white solid: mp=66-67 C; TLC (2:1 hexanes-ethyl acetate) Rf=0.63; 1 H NMR (CDCl3), 6.77 (s, 1H), 6.62 (s, 1H), 3.78 (s, 3H), 3.73 (s, 3H), 3.67 (s, 3H), 2.75 (t, 2H, J=6.3 Hz), 2.63 (t, 2H, J=6.3 Hz), 2.16 (s, 3H). Anal. Calcd for C15 H18 O4: C, 68.69; H: 6.92. Found: C: 68.59; H: 6.53.
Reference: [1] Patent: US6072046, 2000, A,
  • 3
  • [ 185986-76-9 ]
  • [ 6089-09-4 ]
Reference: [1] Journal of the American Chemical Society, 1998, vol. 120, # 36, p. 9228 - 9236
  • 4
  • [ 18498-59-4 ]
  • [ 6089-09-4 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 6, p. 1253 - 1257
[2] ChemPlusChem, 2016, vol. 81, # 11, p. 1160 - 1165
  • 5
  • [ 78181-02-9 ]
  • [ 6089-09-4 ]
Reference: [1] Russian Chemical Bulletin, 2001, vol. 50, # 5, p. 833 - 837
[2] Chemische Berichte, 1938, vol. 71, p. 570
  • 6
  • [ 128545-15-3 ]
  • [ 6089-09-4 ]
Reference: [1] Patent: JP2005/112734, 2005, A, . Location in patent: Page/Page column 7
  • 7
  • [ 78181-02-9 ]
  • [ 6089-09-4 ]
  • [ 36781-65-4 ]
  • [ 88663-49-4 ]
  • [ 88663-50-7 ]
Reference: [1] Russian Chemical Bulletin, 2001, vol. 50, # 5, p. 833 - 837
  • 8
  • [ 21565-82-2 ]
  • [ 6089-09-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 105, p. 289 - 296
  • 9
  • [ 63093-41-4 ]
  • [ 6089-09-4 ]
Reference: [1] Revue Roumaine de Chimie, 1995, vol. 40, # 3, p. 253 - 258
  • 10
  • [ 1431618-30-2 ]
  • [ 64-18-6 ]
  • [ 6089-09-4 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 38, p. 4012 - 4014
  • 11
  • [ 122181-86-6 ]
  • [ 145071-97-2 ]
  • [ 6089-09-4 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 42, p. 6231 - 6234
  • 12
  • [ 92975-31-0 ]
  • [ 6089-09-4 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 9, p. 805 - 816
  • 13
  • [ 5390-04-5 ]
  • [ 6089-09-4 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 3052,3055
  • 14
  • [ 98198-39-1 ]
  • [ 6089-09-4 ]
Reference: [1] Angewandte Chemie, 1955, vol. 67, p. 516
[2] Bulletin de la Societe Chimique de France, 1954, p. 797
[3] Chemische Berichte, 1954, vol. 87, p. 964,969
[4] Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 2568 - 2572[5] Zhurnal Organicheskoi Khimii, 1971, vol. 7, p. 2471 - 2476
[6] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 4, p. 995 - 1005
[7] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 1215 - 1224
[8] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 7, p. 535 - 546
  • 15
  • [ 17920-23-9 ]
  • [ 6089-09-4 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1965, p. 1197 - 1201[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1965, p. 1237 - 1241
  • 16
  • [ 106-96-7 ]
  • [ 105-53-3 ]
  • [ 6089-09-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 582 - 587
  • 17
  • [ 627-15-6 ]
  • [ 105-53-3 ]
  • [ 6089-09-4 ]
  • [ 88663-49-4 ]
  • [ 88663-50-7 ]
Reference: [1] Steroids, 1983, vol. 41, # 3, p. 277 - 284
  • 18
  • [ 6089-09-4 ]
  • [ 38330-80-2 ]
  • [ 100330-50-5 ]
Reference: [1] Synthesis (Germany), 2012, vol. 44, # 13, p. 2005 - 2012
  • 19
  • [ 6089-09-4 ]
  • [ 100330-50-5 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 16, p. 5327 - 5332
  • 20
  • [ 6089-09-4 ]
  • [ 75-65-0 ]
  • [ 149990-27-2 ]
YieldReaction ConditionsOperation in experiment
53% at 0 - 85℃; Preparation 16; But-3-ynyl-carbamic acid tert-butyl ester; Add triethylamine (3 mL) to a solution of 4-pentynoic acid (1.96 g, 20 mmol) in tert-butanol (6 mL) at O0C and then add diphenyl phosphoryl azide (CAUTION: reaction starts violently a short period after the addition). Heat the reaction mixture at 850C overnight under nitrogen. Concentrate in vacuo and purify the crude mixture by chromatography on silica gel eluting with dichloromethane to obtain the title compound as a white solid (1.81g, 53percent).
Reference: [1] Patent: WO2007/28131, 2007, A1, . Location in patent: Page/Page column 49
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