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[ CAS No. 260352-79-2 ]

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Chemical Structure| 260352-79-2
Chemical Structure| 260352-79-2
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Product Details of [ 260352-79-2 ]

CAS No. :260352-79-2 MDL No. :MFCD06797747
Formula : C8H12F2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JHIWVOJDXOSYLW-UHFFFAOYSA-N
M.W :178.18 g/mol Pubchem ID :2761400
Synonyms :

Calculated chemistry of [ 260352-79-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.88
TPSA : 26.3 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) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 2.83
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 2.41
Consensus Log Po/w : 2.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.94 mg/ml ; 0.0109 mol/l
Class : Very soluble
Log S (Ali) : -2.32
Solubility : 0.845 mg/ml ; 0.00474 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.863 mg/ml ; 0.00484 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.54

Safety of [ 260352-79-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 260352-79-2 ]

* 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 [ 260352-79-2 ]
  • Downstream synthetic route of [ 260352-79-2 ]

[ 260352-79-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 260352-79-2 ]
  • [ 107873-03-0 ]
YieldReaction ConditionsOperation in experiment
75% for 14 h; Reflux A colorless solution of butyl 2,2-difluorocyclopropanecarboxylate (1-136) (65.0 g, 330 mmol) in aq .NaOH (750 ml_ H20, 52.5 g NaOH) was refluxed for ~14 hr. A pale yellow solution was formed. The reaction solution was cooled to room temperature, and then concentrated in vacuo to ~250 mL volume. In an ice bath (~0-5 °C), the residue was adjusted to pH ~3-4 using cone, aq. HCI (~70 mL). The resulting solution was extracted with EtOAc (2 x 500 mL). The combined organic layers were dried over Na2S04 and concentrated under high vacuum to give 2,2-difluorocyclopropanecarboxylic acid (1-137) (30 g, 75percent) as a yellow oil which gradually solidified on standing to give a pale yellow solid. 1H NMR (400 MHz, CDCI3) δ ppm 10.78 (s, 1 H), 2.41 - 2.47 (m, 1 H), 2.05 - 2.08 (m, 1 H), 1 .80 -1 .83 (m, 1 H).
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 3, p. 339 - 343
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4104 - 4114
[3] Patent: WO2016/97918, 2016, A1, . Location in patent: Page/Page column 96-97
[4] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3450 - 3456
  • 2
  • [ 141-32-2 ]
  • [ 120801-75-4 ]
  • [ 260352-79-2 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With sodium fluoride In toluene for 1 h; Inert atmosphere; Reflux
Stage #2: for 8 h; Inert atmosphere; Reflux
A solution of butyl prop-2-enoate (80 g, 6.24 mol) and a catalytic amount of NaF (1 .57 g, 375 mmol) in anhydrous toluene (800 ml_) was degassed with nitrogen 3 times, and then refluxed for 1 hr. Then, tri methylsilyl difluoro(fluorosulfonyl)acetate (250 g, 9.99 mol) was added dropwise to the refluxing solution over a period of 40 mins. After the addition, the resulting pale colorless solution was refluxed under N2 for a further 8 hr. The reaction solution was cooled to room temperature to afford a pale yellow solution. The solvent was removed under vacuum at ~45 °C, The combined residue (~130 ml_) was firstly distilled at 130 °C under atmospheric pressure to remove residual toluene, and then distilled under reduced pressure (~0.02 atm) at the same temperature to give butyl 2,2-difluorocyclopropanecarboxylate (1-136) (65 g, 59percent) as a colorless oil. 1H NMR (400 MHz, CDCI3) δ ppm 4.09 - 4.21 (m, 2 H), 2.36 - 2.47 (m, 1 H), 2.04 - 2.07 (m, 1 H), 1 .60 - 1 .66 (m, 3 H), 1 .36 - 1 .42 (m, 2 H), 0.94 (t, J = 7.2 Hz, 3 H).
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 3, p. 339 - 343
[2] Patent: WO2016/97918, 2016, A1, . Location in patent: Page/Page column 96
[3] Organic Syntheses, 2003, vol. 80, p. 172 - 176
  • 3
  • [ 141-32-2 ]
  • [ 260352-79-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2004, vol. 125, # 3, p. 459 - 469
  • 4
  • [ 141-32-2 ]
  • [ 757203-27-3 ]
  • [ 260352-79-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2004, vol. 125, # 3, p. 459 - 469
  • 5
  • [ 111-66-0 ]
  • [ 141-32-2 ]
  • [ 260352-79-2 ]
Reference: [1] Organic Letters, 2000, vol. 2, # 4, p. 563 - 564
  • 6
  • [ 141-32-2 ]
  • [ 260352-79-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2004, vol. 125, # 3, p. 459 - 469
  • 7
  • [ 141-32-2 ]
  • [ 81290-20-2 ]
  • [ 260352-79-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4104 - 4114
[2] Chemical Communications, 2017, vol. 53, # 31, p. 4382 - 4385
  • 8
  • [ 141-32-2 ]
  • [ 260352-79-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2004, vol. 125, # 3, p. 459 - 469
  • 9
  • [ 141-32-2 ]
  • [ 680-15-9 ]
  • [ 260352-79-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 12, p. 5461 - 5464
  • 10
  • [ 141-32-2 ]
  • [ 260352-79-2 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 31, p. 4382 - 4385
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