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[ CAS No. 1680-73-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1680-73-5
Chemical Structure| 1680-73-5
Structure of 1680-73-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1680-73-5 ]

CAS No. :1680-73-5 MDL No. :MFCD03093358
Formula : C7H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :LRPFOCFIHOUPNU-UHFFFAOYSA-N
M.W : 144.60 Pubchem ID :11804892
Synonyms :

Calculated chemistry of [ 1680-73-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.57
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.17
TPSA : 17.07 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) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 1.81
Log Po/w (WLOGP) : 2.25
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 2.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.81
Solubility : 2.24 mg/ml ; 0.0155 mol/l
Class : Very soluble
Log S (Ali) : -1.79
Solubility : 2.36 mg/ml ; 0.0163 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.27 mg/ml ; 0.00875 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.47

Safety of [ 1680-73-5 ]

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 [ 1680-73-5 ]

* 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 [ 1680-73-5 ]
  • Downstream synthetic route of [ 1680-73-5 ]

[ 1680-73-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 108-94-1 ]
  • [ 68-12-2 ]
  • [ 1680-73-5 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: at 0 - 20℃; for 0.5 h;
Stage #2: at 0 - 20℃; for 12 h;
Phosphoryl trichloride (125g, 815mmol) was added dropwise into a flame-dried bottom flask containing N,N-dimethylformamide(74.5g, 1019mmol) at 0 °C with stirring. After addition, the mixture was warmed to ambient temperature for 30 min, and re-cooled to 0°C before the dropwise addition of cyclohexanone (50g, 509mmol). The mixture was warmed to room temperature for 12h.The reaction was poured over ice and quenched with NaHC03. Once neutralized, the mixture was extracted with ethyl acetate (100ml_x3) and washed with water and brine. The organic phase was dried, filtered, and concentrated to afford the product (160g, 87percent yield). 1 H NMR: (CDCI3, 400MHz) δ 1.74~1.75(m, 2H), 1 .76~1 .78(m, 2H), 2.24-2.27 (m,2 H ), 2.53~2.59(m, 2H),7.25 (s, 1 H).
Reference: [1] Synlett, 2014, vol. 25, # 20, p. 2879 - 2882
[2] Organic Letters, 2014, vol. 16, # 17, p. 4662 - 4665
[3] Journal of Organometallic Chemistry, 2011, vol. 696, # 1, p. 179 - 187
[4] Patent: WO2013/43553, 2013, A1, . Location in patent: Page/Page column 115
[5] Organic Letters, 2015, vol. 17, # 15, p. 3734 - 3737
[6] Organic Letters, 2010, vol. 12, # 12, p. 2884 - 2887
[7] Chemical Communications, 2011, vol. 47, # 36, p. 10133 - 10135
[8] Synthetic Communications, 2010, vol. 40, # 16, p. 2441 - 2456
[9] Organic Preparations and Procedures International, 2007, vol. 39, # 2, p. 195 - 199
[10] Chemical and Pharmaceutical Bulletin, 1972, vol. 20, # 2, p. 309 - 313
[11] Journal of the Chemical Society [Section] C: Organic, 1970, p. 2484 - 2488
[12] Tetrahedron Letters, 1977, p. 2027 - 2030
[13] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991, vol. 40, # 11, p. 2228 - 2234[14] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991, # 11, p. 2552 - 2558
[15] Canadian Journal of Chemistry, 1966, vol. 44, p. 45 - 51
[16] Chemische Berichte, 1960, vol. 93, p. 2743 - 2749
[17] Synthesis, 1985, # 5, p. 496 - 497
[18] Synthetic Communications, 1988, vol. 18, # 13, p. 1475 - 1482
[19] Journal of Organic Chemistry, 1994, vol. 59, # 12, p. 3341 - 3346
[20] Journal of Organic Chemistry, 2002, vol. 67, # 24, p. 8400 - 8406
[21] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3736 - 3740
[22] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 63 - 69
[23] Synthesis, 2010, # 9, p. 1428 - 1430
[24] Patent: WO2010/141761, 2010, A2, . Location in patent: Page/Page column 58
[25] Tetrahedron Asymmetry, 2013, vol. 24, # 23, p. 1473 - 1479
[26] Chemical Communications, 2014, vol. 50, # 40, p. 5254 - 5257
[27] Journal of Organic Chemistry, 2014, vol. 79, # 13, p. 6037 - 6046
[28] Patent: WO2016/85939, 2016, A2, . Location in patent: Paragraph 00198
[29] Organic Letters, 2018, vol. 20, # 4, p. 1252 - 1255
[30] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4247 - 4254
  • 2
  • [ 79-01-6 ]
  • [ 108-94-1 ]
  • [ 1680-73-5 ]
Reference: [1] Molecular Pharmacology, 2015, vol. 87, # 3, p. 477 - 491
  • 3
  • [ 50-00-0 ]
  • [ 822-87-7 ]
  • [ 1680-73-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 6, p. 1885 - 1887[2] Angew. Chem., 2014, vol. 54-126, # 6, p. 1905 - 1907,3
  • 4
  • [ 108-94-1 ]
  • [ 1680-73-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2016, vol. 814, p. 42 - 56
  • 5
  • [ 68-12-2 ]
  • [ 1680-73-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 2385,2390
[2] Org. Synth. Coll. Vol., 1973, vol. V, p. 215
  • 6
  • [ 6651-36-1 ]
  • [ 68-12-2 ]
  • [ 1680-73-5 ]
Reference: [1] Synthesis, 1987, # 6, p. 575 - 577
  • 7
  • [ 623-51-8 ]
  • [ 1680-73-5 ]
  • [ 19282-45-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 63 - 69
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