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[ CAS No. 106-86-5 ] {[proInfo.proName]}

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Chemical Structure| 106-86-5
Chemical Structure| 106-86-5
Structure of 106-86-5 * Storage: {[proInfo.prStorage]}

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Product Details of [ 106-86-5 ]

CAS No. :106-86-5 MDL No. :MFCD00022356
Formula : C8H12O Boiling Point : -
Linear Structure Formula :- InChI Key :SLJFKNONPLNAPF-UHFFFAOYSA-N
M.W : 124.18 Pubchem ID :7832
Synonyms :

Calculated chemistry of [ 106-86-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.95
TPSA : 12.53 ?2

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) : -5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 1.68
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.85
Solubility : 1.74 mg/ml ; 0.014 mol/l
Class : Very soluble
Log S (Ali) : -1.97
Solubility : 1.32 mg/ml ; 0.0106 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.99
Solubility : 12.7 mg/ml ; 0.102 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.06

Safety of [ 106-86-5 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:3271
Hazard Statements:H225-H302-H315-H319-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 106-86-5 ]

* 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.

  • Downstream synthetic route of [ 106-86-5 ]

[ 106-86-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 106-86-5 ]
  • [ 143-07-7 ]
  • (+/-)-2<i>t</i>-lauroyloxy-4ξ-vinyl-cyclohexan-<i>r</i>-ol [ No CAS ]
  • 2
  • [ 106-86-5 ]
  • [ 10194-04-4 ]
  • 3
  • [ 106-86-5 ]
  • [ 10217-34-2 ]
  • 5
  • [ 106-86-5 ]
  • (+/-)-2<i>t</i>-ethoxy-4ξ-vinyl-cyclohexan-<i>r</i>-ol [ No CAS ]
  • 6
  • [ 79-21-0 ]
  • [ 100-40-3 ]
  • [ 106-86-5 ]
  • 7
  • [ 100-40-3 ]
  • [ 106-86-5 ]
YieldReaction ConditionsOperation in experiment
Ca. 95% With tert.-butylhydroperoxide; at 79.84℃;Green chemistry; General procedure: Fig. 1 shows reaction scheme for alkene epoxidation. Epoxi-dation of 1-hexene and 4-vinyl-1-cyclohexene with TBHP as anoxidant in the presence of polymer supported catalyst was car-ried out in a jacketed four necked glass reactor of 0.25 L capacity.The batch reactor was equipped with agitator, condenser, digitalthermocouple and water bath. Known quantities of alkene andTBHP were weighed out and introduced into the reactor vessel(no cosolvent was added). Feed mole ratio (FMR) of alkene toTBHP of 1:1-10:1 was selected for charging the reactor. Agita-tion was started at the desired rate, i.e. between 300 and 600 rpmand heating to the reaction mixture was supplied through waterbath via the reactor jacket and monitored by a digital thermo-couple. The temperature of the reaction mixture was allowed toreach the desired value, i.e. 323-353 K and was maintained inthe range of ±0.5 K throughout the batch experiment. A knownamount of catalyst (0.15-0.6 mol% Mo) was weighed and addedinto the reactor when the reaction mixture achieved a constantdesired temperature. The time at which the catalyst was addedwas noted as zero time and a sample was withdrawn, which wasnoted as t = 0. The samples were taken at specific time intervalsand were analysed by Shimadzu GC-2014 gas chromatography(GC). Both PBI.Mo and Ps.AMP.Mo catalysed epoxidations of 1-hexene and 4-vinyl-1-cyclohexene have found to be selective inthe formation of respective epoxides i.e. 1,2-epoxyhexane and4-vinyl-1-cyclohexane 1,2-epoxide. The GC analysis of the reac-tion mixture showed no evidence of either terminal or diepoxidesproducts. Batch experimental results are discussed in Section 3 indetail.
92% (1) To 1000 ml three-mouth flask is added in 105 g 4 - vinyl cyclohexene, 305 g toluene, 113 g acetic anhydride and 10 g sodium acetate, under stirring cooling to 5 C -15 C;(2) Then starting to drop the 100 g 45% hydrogen peroxide, control drop acceleration reaction system temperature is maintained not more than 25 C, about 1.5 hours after the completion of the dropping, after dropping reaction 6 hours;(3) In the system is slowly added 35 g of the commercially available 50% liquid alkali to adjust the pH to 10 - 12, stirring 5 minutes left standstill phase-splitting, separating the upper organic phase;(4) Add 60 g 10% sodium sulfite aqueous solution, stirring 5 minutes left standstill phase-splitting, separating the upper organic phase (pH=10 - 12, starch potassium iodide paper display no peroxide residual), desolution recovery toluene to get the crude product;(5) The crude product of rectification and purification, charge purity of 99% or more fraction 92 g, product yield is up to 92%, the selectivity 99%.
Reference： [1]RSC Advances,2014,vol. 4,p. 32054 - 32062
[2]Applied Catalysis A: General,2013,vol. 466,p. 142 - 152
[3]Journal of the American Chemical Society,2009,vol. 131,p. 12890 - 12891
[4]Patent: CN108101868,2018,A .Location in patent: Paragraph 0027-0068
[5]Journal of the Chemical Society. Perkin transactions I,1997,p. 3115 - 3116
[6]ChemCatChem,2014,vol. 6,p. 2327 - 2332
[7]Journal of Organic Chemistry,1999,vol. 64,p. 2966 - 2968
[8]Tetrahedron Letters,1992,vol. 33,p. 6827 - 6830
[9]Petroleum Chemistry,2006,vol. 46,p. 25 - 27
[10]Journal of Organic Chemistry,1991,vol. 56,p. 469 - 471
[11]Chemistry - A European Journal,2017,vol. 23,p. 4096 - 4107
[12]Journal fur praktische Chemie (Leipzig 1954),1983,vol. 325,p. 893 - 900
[13]Journal of the American Chemical Society,1959,vol. 81,p. 3350,3352
[14]Journal of the American Chemical Society,1959,vol. 81,p. 3350,3352
[15]Patent: US2687406,1951,
[16]Patent: US2714602,1950,
[17]Journal of Organic Chemistry,1988,vol. 53,p. 3587 - 3593
[18]Journal of Organic Chemistry,1993,vol. 58,p. 6421 - 6425
[19]Journal of Organic Chemistry,1988,vol. 53,p. 3587 - 3593
[20]Organic Letters,2008,vol. 10,p. 2291 - 2294
[21]Chemistry - A European Journal,2008,vol. 14,p. 7988 - 7996
[22]Australian Journal of Chemistry,2009,vol. 62,p. 739 - 746
[23]Inorganic Chemistry,2010,vol. 49,p. 7072 - 7079
[24]Advanced Synthesis and Catalysis,2011,vol. 353,p. 231 - 238
[25]Inorganic Chemistry,2012,vol. 51,p. 2725 - 2727
[26]Journal of Molecular Catalysis A: Chemical,2013,vol. 370,p. 64 - 76
[27]Inorganic Chemistry,2013,vol. 52,p. 5077 - 5087
[28]Inorganic Chemistry,2013,vol. 52,p. 5814 - 5823
[29]Organic Process Research and Development,2006,vol. 10,p. 876 - 880
[30]Dalton Transactions,2014,vol. 43,p. 9916 - 9923
[31]Dalton Transactions,2015,vol. 44,p. 17529 - 17543
[32]European Journal of Inorganic Chemistry,2019,vol. 2019,p. 2124 - 2133
  • 8
  • [ 106-86-5 ]
  • [ 31646-64-7 ]
YieldReaction ConditionsOperation in experiment
> 95% With water; at 20℃; for 5h;Conversion of starting material; A 250 ml slurry reactor was loaded with the catalyst (25 g; 16 wt %), deionized water (100 g; 5.55 mol) and 4-vinylcyclohexene-1,2-epoxide (75 g; 0.6 mol). The mixture was vigorously stirred at ambient condition for 5 hours. An end of run sample was taken for analysis by NMR. The conversion of epoxide (compound 1) was >99%, and the yield of diol (compound 2) was >95%.
> 95% With water;Amberlyst 15 resin; at 20℃; for 24h;Conversion of starting material; 63.86 g. VCHO (0.5 mol) was added in a beaker containing 90 g. D.I. water (5 mol) and 30 g. Amberlyst 15 catalyst. The mixture was stirred at room temperature for 24 hrs. The conversion was >99%, and the yield was >95%.
85% With hydrogenchloride; at 20℃; Scheme 3. Metathesis reaction failed to synthesize the target compound.We first attempted the synthesis of a two carbon linker target compound 1 (Scheme 3) by olefin metathesis. In this attempt, we started from the commercial available epoxide (compound72, Scheme 3) which when treated with conc HC1 afforded diol (compound 3, Scheme3) in 85% yield. Tris(cetylpyridinium) 12-tungstophosphate (CWP) catalyzed oxidation of compound 3, Scheme 3, with H202 gave ethylene hexanedioic acid compound 4, Scheme3, in 60% yield. Chlorination of compound 4, Scheme3, with oxalyl chloride and subsequently methylation afforded the dimethyl ester (compound 5, Scheme 3) in 70% yield. Cyclization of compound 5, Scheme3, with acetamidine and potassium tertbutoxide in DMF provided ethylene cyclopenta[d]pyrimidine (compound 6, Scheme 3) in 50% yield. Different conditions including Grubbs j22 and jj23 failed to provide metathesis of compound 6, Scheme3, with 4- methoxycarbonyl styrene. These failures were probably due to the conjugated olefin with the phenyl ring in styrene.
With water;perchloric acid; In tetrahydrofuran; at 0 - 20℃; for 3h; A 1-liter three-neck round flask equipped with a mechanical stirrer, thermometer, and a dropping funnel was charged with 600 mL tetrahydrofuran (THF). 52 mL. VCHO (0.4 mol) was added into the flask. The solution was cooled down to 0 C. in an ice-bath. 22.96 g. perchloric acid (70%) was dissolved in 80 mL D.I. water, and added into the solution dropwise during a period of one hour. The solution temperature was controlled at below 5 C. After the addition of perchloric acid, the ice-bath was removed, and the solution was stirred for 2 hrs at room temperature. Then, 28-g. potassium carbonate in 40 mL water was added to neutralize perchloric acid. The mixture was roto-vaporated to remove some THF. The residue was extracted with ether. After drying the ether solution with anhydrous potassium sulfate, the ether solvent was removed by rotovap. The crude VCHD was distilled at a reduced pressure. VCHD product was collected at 99-106 C. under 0.05 mm Hg. pressure.

  • 9
  • [ 106-86-5 ]
  • [ 31646-64-7 ]
  • [ 83185-49-3 ]
  • [ 83185-50-6 ]
  • 10
  • [ 106-86-5 ]
  • 3-amino-4-hydroxy-1-vinylcyclohexane [ No CAS ]
  • 4-amino-3-hydroxy-1-vinylcyclohexane [ No CAS ]
  • 11
  • [ 632-21-3 ]
  • [ 100-40-3 ]
  • [ 106-87-6 ]
  • [ 106-86-5 ]
  • [ 5116-65-4 ]
  • [ 78950-58-0 ]
  • 12
  • [ 100-40-3 ]
  • [ 106-87-6 ]
  • [ 106-86-5 ]
  • [ 5116-65-4 ]
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