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Product Details of [ 2067-33-6 ]

CAS No. :2067-33-6 MDL No. :MFCD00004414
Formula : C5H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WNXNUPJZWYOKMW-UHFFFAOYSA-N
M.W : 181.03 Pubchem ID :16368
Synonyms :

Calculated chemistry of [ 2067-33-6 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.79
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) : -6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.35
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 1.2
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.55
Solubility : 5.12 mg/ml ; 0.0283 mol/l
Class : Very soluble
Log S (Ali) : -1.74
Solubility : 3.33 mg/ml ; 0.0184 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.72
Solubility : 3.42 mg/ml ; 0.0189 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 2067-33-6 ]

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 [ 2067-33-6 ]

* 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 [ 2067-33-6 ]
  • Downstream synthetic route of [ 2067-33-6 ]

[ 2067-33-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 2067-33-6 ]
  • [ 506-26-3 ]
Reference: [1] Synthesis, 1998, # 7, p. 1015 - 1018
  • 2
  • [ 2067-33-6 ]
  • [ 34626-51-2 ]
Reference: [1] Journal of the American Chemical Society, 1996, vol. 118, # 50, p. 12541 - 12554
[2] Helvetica Chimica Acta, 1993, vol. 76, p. 1901 - 1915
[3] Farmaco, 1992, vol. 47, # 3, p. 379 - 385
[4] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 10, p. 1856 - 1861
  • 3
  • [ 67-56-1 ]
  • [ 2067-33-6 ]
  • [ 5454-83-1 ]
YieldReaction ConditionsOperation in experiment
99% at 110℃; Flow reactor General procedure: Lauric acid (1a) (2.01 g, 10.0 mmol) was dissolved in methanol (10 mL) and then placed in a syringe, which wasthen attached to a syringe pump. The methanol solution was fedinto a stainless steel column (inner volume: 0.53 mL, 4.0 mm i.d. © 50 mm) filled in HO-SAS (334 mg) with a flow rate of0.177 mL.min-1. The column was immersed into an oil bath(110°C). A back-pressure regulator (75 psi) was connected.The reaction mixture was collected from the outlet. The reaction mixture eluted during the first 10 min was discarded. Thereaction mixture was collected during 3 min and added n-decane as an internal standard for GC analysis. The followingportion was collected for a 30 min period in a glass flask, andsolvent was evaporated. The crude mixture was purified byflash column chromatography on SiO2 (hexane/ethyl acetate =5/1) to give 3a (1.13 g, 99percent).
Reference: [1] Journal of Materials Chemistry B, 2013, vol. 1, # 34, p. 4225 - 4230
[2] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 5, p. 607 - 612
[3] Organic Letters, 2015, vol. 17, # 1, p. 138 - 141
[4] Synlett, 2004, # 10, p. 1735 - 1738
[5] New Journal of Chemistry, 2001, vol. 25, # 9, p. 1182 - 1184
[6] Heterocycles, 2017, vol. 94, # 8, p. 1518 - 1541
[7] Journal of the American Chemical Society, 1938, vol. 60, p. 1375
[8] Collection of Czechoslovak Chemical Communications, 1967, vol. 32, # 3, p. 1035 - 1044
[9] Tetrahedron Letters, 1999, vol. 40, # 17, p. 3471 - 3474
[10] Journal of the American Chemical Society, 1999, vol. 121, # 49, p. 11425 - 11431
[11] Organic and Biomolecular Chemistry, 2009, vol. 7, # 9, p. 1821 - 1828
[12] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 6981 - 6995
[13] Angewandte Chemie - International Edition, 2014, vol. 53, # 13, p. 3400 - 3404[14] Angew. Chem., 2014, vol. 126, # 13, p. 3468 - 3472,5
[15] Supramolecular Chemistry, 2014, vol. 26, # 1, p. 25 - 31
  • 4
  • [ 186581-53-3 ]
  • [ 2067-33-6 ]
  • [ 5454-83-1 ]
Reference: [1] Molecules, 2006, vol. 11, # 6, p. 435 - 443
[2] Journal of Organometallic Chemistry, 1983, vol. 253, # 1, p. 31 - 38
  • 5
  • [ 64-17-5 ]
  • [ 2067-33-6 ]
  • [ 14660-52-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 563 - 566
[2] Journal of Organic Chemistry, 1980, vol. 45, # 16, p. 3215 - 3227
[3] Tetrahedron Letters, 1988, vol. 29, # 50, p. 6557 - 6560
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 9, p. 2187 - 2190
[5] Chinese Journal of Chemistry, 2014, vol. 32, # 2, p. 157 - 162
[6] Langmuir, 2016, vol. 32, # 14, p. 3340 - 3347
[7] Tetrahedron, 2017, vol. 73, # 44, p. 6275 - 6285
  • 6
  • [ 2067-33-6 ]
  • [ 14660-52-7 ]
Reference: [1] Patent: EP748310, 1999, B1,
[2] Patent: US5827881, 1998, A,
  • 7
  • [ 67-56-1 ]
  • [ 2067-33-6 ]
  • [ 50995-48-7 ]
Reference: [1] Patent: US2017/197986, 2017, A1, . Location in patent: Paragraph 0670; 0671; 0672
  • 8
  • [ 2067-33-6 ]
  • [ 603-35-0 ]
  • [ 17814-85-6 ]
YieldReaction ConditionsOperation in experiment
88% for 48 h; Inert atmosphere; Reflux General procedure: A mixture of ω-bromocarboxylic acid (1 equiv) and triphenylphosphine (1 equiv) in 300 mL of toluene was refluxed for 48 h under argon. The mixture was allowed to cool at room temperature and concentrated in vacuum. The residue was crystallized from various solvents to give the corresponding phosphonium salt.
50% at 80℃; for 48 h; 5-bromopentanoic acid (5.01 g, 0.03 mol) and triphenylphosphine (2.62 g, 0.01 mol) were added to a 100 mL flask, 50 mL of acetonitrile was added and the mixture was heated to 80 ° C for 48 hours. After the reaction was completed, the solvent was spin dried. The reaction system was introduced into cyclohexane to collect precipitated oily precipitate and vacuum-dried product in a yield of 50percent.
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 3196 - 3206
[2] Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 697 - 704
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[4] Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4449 - 4453
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6353 - 6363
[6] Patent: CN104844650, 2017, B, . Location in patent: Paragraph 0143; 0144; 0145
[7] Journal of the American Chemical Society, 1969, vol. 91, p. 4933 - 4934
[8] Tetrahedron, 1993, vol. 49, # 46, p. 10501 - 10510
[9] Journal of Medicinal Chemistry, 1985, vol. 28, # 3, p. 287 - 294
[10] Tetrahedron Letters, 1996, vol. 37, # 9, p. 1393 - 1396
[11] Bioscience, Biotechnology and Biochemistry, 2001, vol. 65, # 9, p. 2065 - 2069
[12] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6467 - 6472
[13] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1905 - 1916
[14] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1718 - 1729
[15] Applied Catalysis A: General, 2014, vol. 470, p. 183 - 188
[16] Organic Letters, 2016, vol. 18, # 3, p. 504 - 507
[17] Organic Letters, 2017, vol. 19, # 18, p. 4940 - 4943
[18] Patent: CN104513186, 2016, B, . Location in patent: Paragraph 0126 - 0128
[19] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 275 - 284
  • 9
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  • [ 38562-01-5 ]
Reference: [1] Patent: CN106810484, 2017, A,
  • 10
  • [ 2067-33-6 ]
  • [ 75-65-0 ]
  • [ 88987-42-2 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 0.5 h;
Stage #2: at 0 - 20℃; for 0.25 h;
28-1 A 28-2A To a solution of 28-1A (5 g, 27.62 mmol) in DCM, added oxalyl chloride (5.2 g, 41.436 mmol) and catalytic amount of DMF at 0 °C and stirred at RT for 30 min, then added i-BuOH (8.2 g, 110.49 mmol) at 0 °C and stirred at RT for 15 min. The reaction mixture completely distilled off, then added water (100 mL) and extracted with EtOAc (100 mL). The organic layer washed with water (50 mL), NaHC03 solution (50 mL) and dried over Na2S04, and the organic phase was concentrated under reduced pressure. The crude compound was purified using silica gel chromatography (3percent EtOAc in hexanes) to afford 28-2A (5 g, 21.18 mmol, 77percent yield) as a colorless oily liquid.
62.6%
Stage #1: With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5 h; Cooling with ice
Stage #2: at 20℃;
5-bromo-pentanoic acid (5g, 27.62mmol) in dry DCM solution to this while stirring with ice cold N,N'-dimethylaminopyridine (1.68g, 13.75mmol) and DCC (6.83g, 33.15mmol) was added successively. After half an hour was added to tert-butanol (15.8ml, 165.75mmol) in the reaction mixture. The resulting solution was stirred overnight at room temperature. Was then diluted with DCM and washed with successive water and brine. The organic layer was dried and the solvent was evaporated. Using hexane-ethyl acetate to 1percent solution of the residue was purified by chromatography to give the pure tert-butyl 5-bromopentanoate 4.1g (62.6percent yield) of a pale yellow liquid.
Reference: [1] Patent: WO2015/6740, 2015, A2, . Location in patent: Page/Page column 182; 183
[2] Patent: WO2016/154241, 2016, A1, . Location in patent: Paragraph 670; 671
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 37, p. 5180 - 5192
[4] Patent: KR101569966, 2015, B1, . Location in patent: Paragraph 0145; 0146
[5] Patent: WO2011/53519, 2011, A1, . Location in patent: Page/Page column 27-28
  • 11
  • [ 2067-33-6 ]
  • [ 115-11-7 ]
  • [ 88987-42-2 ]
Reference: [1] Organic Letters, 2000, vol. 2, # 15, p. 2315 - 2317
[2] Synlett, 1998, # 6, p. 671 - 675
[3] Tetrahedron Letters, 1998, vol. 39, # 32, p. 5759 - 5762
[4] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1993, # 14, p. 2141 - 2146
  • 12
  • [ 2067-33-6 ]
  • [ 71432-55-8 ]
  • [ 88987-42-2 ]
YieldReaction ConditionsOperation in experiment
7.4 g for 120 h; Diisopropylcarbodiimide (25.2 g; 0.2 mol), tert-butyl alcohol (14.8 g; 0.2 mol) and CuCl (0.5 g) was stirred overnight at rt. 5-Bromovaleric acid (10.0 g; 55.7 mmol) was dissolved in 150 mL of dichloromethane, and the crude tert-butyl isourea generated in situ was added in 15 equal portions (approximately 3 mL of each) over the period of 5 days. Any increase in the temperature of the reaction mixture above 30 °C led to a rapid decomposition of the alkylating agent. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel using a linear gradient of diethyl ether in petroleum ether. Yield: 7.4 g (56percent). Colorless liquid, Rf = 0.81 (S8). 1H NMR (600 MHz, CDCl3): δ = 3.42 (t, J = 6.7 Hz, 2H), 2.25 (t, J = 7.4 Hz, 2H), 1.88 (m, 2H), 1.74 (m, 2H), 1.45 (s, 9H, t-Bu). 13C NMR (150.9 MHz, CDCl3): δ = 172.47 (-CO-O), 80.28, 34.47, 33.14, 31.95, 28.04 (3C), 23.60. IR (film) νmax (cm-1): 1729 vs (C=O); 2978 m, 2934 m, 1367 s (CH3). 1156 vs (C-O). HRMS (ESI) calc for C9H17O2BrNa [M + Na]+ 259.03041, found: 259.03037.
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 256 - 275
  • 13
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  • [ 385425-15-0 ]
Reference: [1] Patent: US2015/353541, 2015, A1,
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  • [ 2067-33-6 ]
  • [ 473927-64-9 ]
Reference: [1] Patent: US2015/353541, 2015, A1,
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