37909-95-8|4-Butyl-1,1'-Biphenyl| Ambeed

CAS No. :	37909-95-8
Formula :	C₁₆H₁₈
M.W :	210.31
SMILES Code :	CCCCC1=CC=C(C2=CC=CC=C2)C=C1
MDL No. :	MFCD00100665
InChI Key :	JZDZRFNMDCBTNS-UHFFFAOYSA-N
Pubchem ID :	2775237

Safety of [ 37909-95-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 37909-95-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	12
Fraction Csp3	0.25
Num. rotatable bonds	4
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	71.27
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.2
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	6.01
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.7
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	5.83
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	5.11
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.22
Solubility	0.00126 mg/ml ; 0.00000601 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-5.79
Solubility	0.000343 mg/ml ; 0.00000163 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-6.52
Solubility	0.0000632 mg/ml ; 0.000000301 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-3.32 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.61

Application In Synthesis of [ 37909-95-8 ]

* 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 [ 37909-95-8 ]

[ 37909-95-8 ] Synthesis Path-Downstream 1~54

1
[ 108-30-5 ]
[ 37909-95-8 ]
[ 102553-53-7 ]

References: [1]Nippon Kagaku Zasshi,1957,vol. 78,p. 1577,1580.
Chem.Abstr.,1960,p. 1413.

2
[ 13211-01-3 ]
[ 37909-95-8 ]

References: [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1954,vol. 57,p. 845.
    Chem.Abstr.,1955,p. 10898.
[2]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399.
    Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376.
[3]Journal of the American Chemical Society,1975,vol. 97,p. 4620 - 4626.
[4]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191.
    Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310.
[5]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 853 - 862.

3
[ 93017-33-5 ]
[ 37909-95-8 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 608,611; engl. Ausg. S. 589, 591.

4
[ 92-52-4 ]
[ 71-36-3 ]
[ 37909-95-8 ]
[ 7641-81-8 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 413,416; engl. Ausg. S. 405, 407.
[2],1957,vol. IV 14,p. 49,56.
Chem.Abstr.,1960,p. 24565.

5
[ 37909-88-9 ]
[ 37909-95-8 ]

References: [1]Bulletin de la Societe Chimique de France,1972,p. 1581 - 1587.

6
[ 37909-95-8 ]
[ 93189-65-2 ]

References: [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399.
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376.

7
[ 37909-95-8 ]
[ 141-75-3 ]
[ 102168-20-7 ]

References: [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399.
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376.

8
[ 37909-95-8 ]
[ 84941-14-0 ]
[ 93972-13-5 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191.
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310.

11
[ 109-72-8 ]
(η⁶:η⁶-biphenyl)bis(tricarbonylchromium) [ No CAS ]
[ 37909-95-8 ]
[ 54532-97-7 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 2073 - 2076.

12
4-butyl-N,N,N-trimethylphenylaminium trifluoromethanesulfonate [ No CAS ]
[ 98-80-6 ]
[ 37909-95-8 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 6046 - 6047.

13
[ 109-65-9 ]
[ 1137-79-7 ]
[ 37909-95-8 ]

References: [1]Synthesis,2003,p. 2811 - 2814.

14
[ 693-03-8 ]
[ 2051-62-9 ]
[ 37909-95-8 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 15922 - 15934.

15
[ 698378-27-7 ]
[ 37909-95-8 ]

References: [1]European Journal of Organic Chemistry,2004,p. 1544 - 1557.

16
[ 15499-27-1 ]
[ 98-80-6 ]
[ 37909-95-8 ]

References: [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 1871 - 1876.
[2]Journal of the American Chemical Society,2005,vol. 127,p. 4685 - 4696.
[3]Organometallics,2018,vol. 37,p. 1876 - 1883.

17
[ 92-66-0 ]
[ 15676-66-1 ]
[ 37909-95-8 ]

References: [1]Synthesis,2005,p. 485 - 492.

18
[ 41492-05-1 ]
[ 3958-47-2 ]
[ 37909-95-8 ]

References: [1]Synthesis,2005,p. 485 - 492.

19
[ 15499-27-1 ]
[ 29540-83-8 ]
[ 960-16-7 ]
[ 644-08-6 ]
[ 37909-95-8 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 6343 - 6348.

20
[ 41492-05-1 ]
[ 98-80-6 ]
[ 37909-95-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With C24H20Cl2NPPdS; potassium carbonate; palladium; In toluene; at 100℃; for 2h;	General procedure: A 100 ml round bottom flask was fitted with a reflux condenser and a magnetic stirrer bar. The flask was charged with toluene (15 ml) and the appropriate amount of catalyst reagents and the internal standard (n-Decane: 2.59 mmol). The contents were thoroughly mixed and an initial sample (t0) was then taken. The reaction flask was placed in an oil bath at the desired temperature and the reaction mixture allowed to heat/reflux with stirring. A sample was taken and analyzed every 10 min for the first hour and every 30 min thereafter until t3h. In cases where conversionwas not complete after 3 h, the reaction mixturewas then allowed to stir for a total of 24 h. The reaction at 140 C was performed in a sealed tube. All catalytic reactions were done under aerobic conditions. Percentage conversions were determined by GC with n-decane as the internal standard and the coupling products were characterized by mass spectrometry (Table 4) as well as 1H NMR spectroscopy (Entry 5, Table 4 only).

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 3190 - 3198.
[2]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 551 - 555.
[3]Applied Organometallic Chemistry,2015,vol. 29,p. 87 - 89.
[4]Journal of Organometallic Chemistry,2012,vol. 703,p. 34 - 42.
[5]Angewandte Chemie - International Edition,2006,vol. 45,p. 2868 - 2871.
[6]Chemistry - A European Journal,2010,vol. 16,p. 1812 - 1818.
[7]Organometallics,2010,vol. 29,p. 1729 - 1739.
[8]Applied Catalysis A: General,2011,vol. 393,p. 231 - 241.
[9]Organometallics,2011,vol. 30,p. 6270 - 6282.
[10]Journal of Organometallic Chemistry,2018,vol. 868,p. 76 - 85.

21
[ 37909-95-8 ]
[ 63619-54-5 ]

References: [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 853 - 862.

22
[ 92-52-4 ]
[ 37909-95-8 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191.
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310.

23
[ 37909-95-8 ]
[ 52709-83-8 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191.
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310.

24
[ 37909-95-8 ]
[ 93972-06-6 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191.
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310.

25
[ 3218-36-8 ]
KMnO₄ [ No CAS ]
[ 37909-95-8 ]

References: [1]European Journal of Organic Chemistry,2004,p. 1544 - 1557.
[2]European Journal of Organic Chemistry,2004,p. 1544 - 1557.

26
[ 698377-55-8 ]
[ 37909-95-8 ]

References: [1]European Journal of Organic Chemistry,2004,p. 1544 - 1557.
[2]European Journal of Organic Chemistry,2004,p. 1544 - 1557.

27
[ 37909-95-8 ]
[ 102168-34-3 ]

References: [1]Nippon Kagaku Zasshi,1957,vol. 78,p. 1577,1580.
Chem.Abstr.,1960,p. 1413.

28
[ 92-52-4 ]
sodium [ No CAS ]
[ 37909-95-8 ]

References: [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399.
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376.

29
[ 37909-95-8 ]
[ 7641-81-8 ]

References: [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399.
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376.

30
[ 37909-95-8 ]
[ 96624-48-5 ]

References: [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399.
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376.

31
aluminiumchlorid [ No CAS ]
[ 37909-95-8 ]
[ 75-36-5 ]
[ 59662-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	In nitrobenzene;	Example 58 Intermediate 58A 1-(4'-butyl[1,1'-biphenyl]-4-yl)-1-ethanone 5g (24mmol) <strong>[37909-95-8]4-butylbiphenyl</strong> and 3.96g (30mmol) aluminiumchlorid are dissolved in 30ml nitrobenzene. At a temperature below 20C 1.87g (30mmol) acetylchloride is added dropwise and the reactionmixture is stirred at roomtemperature for 2hrs. The solution is poured onto icewater, the organic phase is separated, the aqueous phase extracted with ethylacetate, the combined organic phases are washed with water and brine, dried and concentrated. The product is obtained by trituration with petrolether. Yield: 3.07g (51%). 200 MHz 1H-NMR (CDCl3): 0.96, t, 3H; 1.40, m, 2H; 1.65, m, 2H; 2.62, s, 3H; 2.68, t, 2H; 7.30, d, 2H; 7.58, d, 2H; 7.69, d, 2H; 8.02, d, 2H.

References: [1]Patent: EP1031349,2000,A1 .

32
[ 37909-95-8 ]
[ 13211-01-3 ]
[ 92-92-2 ]

References: [1]Synlett,2009,p. 117 - 121.

33
[ 693-03-8 ]
[ 1009828-67-4 ]
[ 37909-95-8 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 9566 - 9569.

34
[ 1625-92-9 ]
[ 92-52-4 ]
[ 7116-95-2 ]
[ 644-08-6 ]
[ 5707-44-8 ]
[ 37909-95-8 ]
[ 10289-45-9 ]

References: [1]Petroleum Chemistry,2010,vol. 50,p. 149 - 153.

35
[ 109-65-9 ]
[ 3315-91-1 ]
[ 37909-95-8 ]

References: [1]Asian Journal of Chemistry,2011,vol. 23,p. 4087 - 4089.
[2]Asian Journal of Chemistry,2013,vol. 25,p. 6303 - 6305.

36
[ 15499-27-1 ]
[ 100-58-3 ]
[ 37909-95-8 ]

References: [1]Chemistry Letters,2011,vol. 40,p. 936 - 938.

37
[ 92-69-3 ]
[ 37909-95-8 ]

References: [1]Organic Letters,2013,vol. 15,p. 96 - 99.
[2]Organic Letters,2013,vol. 15,p. 96 - 99.

38
[ 76996-40-2 ]
[ 693-04-9 ]
[ 37909-95-8 ]

References: [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2329 - 2336.
[2]Organic Letters,2013,vol. 15,p. 96 - 99.
[3]ChemSusChem,2018,vol. 11,p. 1290 - 1294.
[4]European Journal of Organic Chemistry,2017,vol. 2017,p. 7271 - 7276.

39
[ 405201-85-6 ]
[ 693-04-9 ]
[ 37909-95-8 ]

References: [1]Organic Letters,2013,vol. 15,p. 96 - 99.

40
[ 20651-67-6 ]
[ 71-43-2 ]
[ 37909-95-8 ]

References: [1]Chemical Communications,2013,vol. 49,p. 2983 - 2985.

41
[ 15499-27-1 ]
[ 71-43-2 ]
[ 37909-95-8 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 6016 - 6024.

42
[ 15499-27-1 ]
[ 591-51-5 ]
[ 37909-95-8 ]

References: [1]Organic Letters,2013,vol. 15,p. 5114 - 5117.
[2]Chemistry - A European Journal,2016,vol. 22,p. 3991 - 3995.

43
[ 15499-27-1 ]
[ 591-51-5 ]
[ 37909-95-8 ]
[ 7641-81-8 ]

References: [1]Organic Letters,2013,vol. 15,p. 5114 - 5117.

44
C₂₁H₂₂OSi [ No CAS ]
[ 74-88-4 ]
[ 37909-95-8 ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 12719 - 12722.
Angew. Chem.,2013,vol. 125,p. 12951 - 12954,4.

45
[ 542-69-8 ]
C₂₁H₂₂OSi [ No CAS ]
[ 37909-95-8 ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 12719 - 12722.
Angew. Chem.,2013,vol. 125,p. 12951 - 12954,4.

46
[ 20651-67-6 ]
[ 98-80-6 ]
[ 37909-95-8 ]

References: [1]Green Chemistry,2013,vol. 15,p. 3396 - 3403.

47
[ 591-50-4 ]
[ 145240-28-4 ]
[ 37909-95-8 ]

Yield	Reaction Conditions	Operation in experiment
34%		In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below.

References: [1]Journal of Materials Chemistry A,2014,vol. 2,p. 12739 - 12745.
[2]Tetrahedron,2017,vol. 73,p. 5784 - 5793.
[3]Chemical Communications,2014,vol. 50,p. 12356 - 12359.

48
[ 37909-95-8 ]
C₁₀₀H₁₂₀N₈O₁₂ [ No CAS ]
2C₁₀₀H₁₂₀N₈O₁₂*C₁₆H₁₈ [ No CAS ]

References: [1]Journal of Physical Organic Chemistry,2015,vol. 28,p. 187 - 190.

49
[ 15499-27-1 ]
[ 591-51-5 ]
[ 104-51-8 ]
[ 37909-95-8 ]

References: [1]Chemistry - A European Journal,2016,vol. 22,p. 3991 - 3995.

50
[ 109-72-8 ]
[ 1591-31-7 ]
[ 37909-95-8 ]

References: [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 3043 - 3046.

51
[ 591-50-4 ]
[ 2525-42-0 ]
[ 18162-48-6 ]
[ 145240-28-4 ]
[ 37909-95-8 ]
[(2Z)-3-(benzenesulfonyl)-2-phenylprop-2-en-1-yl]oxy}(tert-butyl)dimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%; 64%		In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below.

References: [1]Tetrahedron,2017,vol. 73,p. 5784 - 5793.

52
C₅₄H₄₅O₃P₂PdS⁽¹⁺⁾*BF₄^(1-) [ No CAS ]
[ 18162-48-6 ]
[ 145240-28-4 ]
[ 37909-95-8 ]
[(2Z)-3-(benzenesulfonyl)-2-phenylprop-2-en-1-yl]oxy}(tert-butyl)dimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%; 80%		In an N2 charged glove box with oxygen and water levels ?0.1 ppm, to an oven-dried screwed vial were added complex 8 (51 mg, 0.05 mmol), K2CO3 (13.8 mg, 0.1 mmol, 2 eq.), boronic acids 3a (9 mg, 0.05mmol, 1 eq.) and THF (3 mL), then phenyl iodide 2a (10 mg, 0.05 mmol, 1 eq.) were also charged into the reaction mixture. The joint position between the vial and cap was sealed with black electric tape to save the nitrogen in the vial and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13 hours on the IKA electric stirring machine. After 15 hours, imidazole (17 mg, 0.25 mmol, 5 eq.) and TBSCl (22 mg, 0.15 mmol, 3 eq.) were added into the vial under air and stirred for another 2 hours at room temperature, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the formation of TBS protected allyl alcohol 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a (7 mg, 80%). The spectrum was same as above. The biphenyl product 4aa is also formed with about 1.6 mg (15% yield). There is no reaction occur without the presence of phenyl iodide, which was confirmed by the analysis of 31P NMR of crude reaction mixture.

References: [1]Tetrahedron,2017,vol. 73,p. 5784 - 5793.

53
[ 109-69-3 ]
[ 2920-38-9 ]
[ 74-88-4 ]
[ 37909-95-8 ]
4-butyl-4-phenylcyclohexa-2,5-dienone [ No CAS ]
trans-4-butyl-1-methyl-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
cis-4-butyl-1-methyl-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%Spectr.; 9%Spectr.		General procedure: To a suspension of the DA 12- sodium salt, butyl chloride or cyclohexyl bromide (1 equiv.) was added dropwise at -40 C and the reaction mixture was kept at the same conditions for 40÷60 min. Afterwards required alkyl bromide (1.1÷1.4 equiv.) was added (Table 1, entries 2÷5) and reaction mixture was treated as described above for dienone 2.

References: [1]Tetrahedron,2018,p. 842 - 851.

54
[ 109-69-3 ]
[ 25542-62-5 ]
[ 2920-38-9 ]
[ 37909-95-8 ]
trans-4-butyl-1-(6-ethoxy-6-oxohexyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
cis-4-butyl-1-(6-ethoxy-6-oxohexyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%Spectr.		General procedure: To a suspension of the DA 12- sodium salt, butyl chloride or cyclohexyl bromide (1 equiv.) was added dropwise at -40 C and the reaction mixture was kept at the same conditions for 40÷60 min. Afterwards required alkyl bromide (1.1÷1.4 equiv.) was added (Table 1, entries 2÷5) and reaction mixture was treated as described above for dienone 2.

References: [1]Tetrahedron,2018,p. 842 - 851.

Historical Records

Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Vilsmeier-Haack Reaction

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CAS No.: 37909-95-8

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CAS No.: 37909-95-8

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[ 37909-95-8 ] Synthesis Path-Downstream 1~54

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