[ CAS No. 57002-01-4 ] {[proInfo.proName]}

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Quality Control of [ 57002-01-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 57002-01-4 ]

Product Details of [ 57002-01-4 ]

CAS No. :	57002-01-4	MDL No. :	MFCD01074615
Formula :	C₈H₁₅BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	154.01	Pubchem ID :	-
Synonyms :

Safety of [ 57002-01-4 ]

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 [ 57002-01-4 ]

* 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 [ 57002-01-4 ]

[ 57002-01-4 ] Synthesis Path-Downstream 1~88

1
[ 57002-01-4 ]
[ 42599-23-5 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6075 - 6079
[2]Journal of the American Chemical Society,1973,vol. 95,p. 5786 - 5788

2
[ 57002-01-4 ]
[ 67404-69-7 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6068 - 6075

3
[ 57002-01-4 ]
[ 67478-59-5 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6079 - 6084

4
[ 57002-01-4 ]
E,E-4-[R*,R*-5-(2,2-Dibromoethenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenyl-1,3-pentadiene [ No CAS ]
E,E-4-[R*,R*-5-(1E,3E-2-Bromo-4-cyclohexyl-1,3-butadienyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenyl-1,3-pentadiene [ No CAS ]
E,E-4-[R*,R*-5-(1Z,3E-2-Bromo-4-cyclohexyl-1,3-butadienyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenyl-1,3-pentadiene [ No CAS ]

Reference： [1]Synlett,2000,p. 374 - 378

6
[ 880263-69-4 ]
[ 57002-01-4 ]
[ 880263-77-4 ]

Reference： [1]Synthesis,2006,p. 299 - 304

7
[ 929078-65-9 ]
[ 57002-01-4 ]
5-cyclohexyl-3-ethyl-penta-2,4-dienoic acid methyl ester [ No CAS ]

Reference： [1]Synlett,2006,p. 3457 - 3460

8
[ 57002-01-4 ]
[ 431-03-8 ]
C₁₂H₂₀O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 8266 - 8269

9
[ 57002-01-4 ]
[ 97483-77-7 ]
[ 928648-83-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 90℃;	Preparation 38; (E)-2-Aminomethyl-5-(2-cyclohexylvinyl)-pyridine; (E)-5-(2-Cyclohexylvinyl)-pyridine-2-carbonitrile; Combine a mixture of 5-bromo-2- cyano-pyridine (2 g, 10.93 mmol), 2-cyclohexylvinyl boronic acid (2.52 g, 16.39 mmol), [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with DCM (446 mg, 0.546 mmol) and 2M aqueous Na2CO3 (18.2 mL, 36.07 mmol) in 1,4-dioxane (110 mL). Purge with nitrogen and heat at 90C overnight. Cool the reaction to room temperature and partition between EtOAc and water. Separate the aqueous phase and extract with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (120 g, pre-packed cartridge) eluting stepwise with hexane/EtOAc (1:0 over 5 min, 49:1 over 5 min and 19:1 over 5 min; 50 mL/min) to obtain the desired intermediate (1.76 g, 76%). MS (APCI+) m/z: 213 (M+H)+.

Reference： [1]Patent: WO2007/28083,2007,A2 .Location in patent: Page/Page column 86-87

10
[ 57002-01-4 ]
[ 285119-72-4 ]
[ 928648-81-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium carbonate In 1,4-dioxane; water at 90℃;	37 (E)-3-(tert-Butoxycarbonylamino-methyl)-6-(2-cvclohexylvinyl)-pyridine; Combine 3- (tert-butoxycarbonylamino-methyl)-6-chloropyridine (1.42 g, 5.85 mmol), 2- cyclohexylvinyl boronic acid (1.35 g, 8.78 mmol), [l,l'-bis(diphenylphosphino)- ferrocene]dichloropalladium(II) complex with DCM (239 mg, 0.293 mmol), and 2M aqueous Na2CO3 (9.65 mL, 19.2 mmol) in 1,4-dioxane (60 mL). Purge the resulting solution with nitrogen for 5 min and heat at 90°C overnight. Cool the reaction mixture to room temperature and partition the mixture between EtOAc and water. Separate the aqueous phase and extract twice with EtOAc. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (120 g, pre-packed cartridge) eluting stepwise with hexane/ΕtOAc (1:0 over 5 min, 49:1 over 5 min, 19:1 over 5 min, 9:1 over 5 min and 85:15 over 5 min; 50 mL/min) to obtain the desired intermediate (1.3 g, 70%). MS (APCI+) m/z: 317 (M+H)+.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2007/28083, 2007, A2 Location in patent: Page/Page column 86

11
[ 938433-81-9 ]
[ 57002-01-4 ]
[ 936760-51-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 90℃; for 6.5h;	Preparation of 1-[3-((E)-2-cyclohexylvinyl)pyrido[2,3-b]pyrazin-6-yl]-3-ethylurea (Reaction According to Scheme 6) 99.6 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.40 mmol), 73.6 mg of cyclohexylvinylboronic acid (0.48 mmol), 84.4 mg of sodium carbonate (0.80 mmol) and 33.4 mg of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.04 mmol) were initially charged in 6 ml of dimethylformamide/water (1:1) under nitrogen. The mixture was then heated to 90 C. for 6.5 h. Distilled water was then added to the reaction mixture and the resulting precipitate was filtered off with suction. The further purification was effected by column chromatography on silica gel (ethyl acetate/heptane eluent mixture). A light brown solid was obtained. m.p.: 202-204 C. (decomp.) ESI-MS: found m/z=326.0 (M+H+); calc. 325 amu 1H NMR (d6-DMSO): delta=1.10-1.40 (m, 8H), 1.65-1.90 (m, 5H), 2.28-2.38 (m, 1H), 3.25-3.35 (m, 2H), 6.69 (d, 1H), 7.15 (dd, 1H), 7.58 (d, 1H), 8.28 (d, 1H), 8.98 (s, 1H), 9.15 (s, 1H), 10.05 (s, 1H) ppm.

Reference： [1]Patent: US2007/149484,2007,A1 .Location in patent: Page/Page column 103-104

12
[ 916672-81-6 ]
[ 57002-01-4 ]
C₃₄H₄₂N₂O₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 4010 - 4019

13
[ 1003321-67-2 ]
[ 57002-01-4 ]
C₄₂H₄₂N₂O₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 4010 - 4019

14
[ 16425-70-0 ]
[ 57002-01-4 ]
C₃₂H₃₈N₂O₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 4010 - 4019

15
[ 14011-60-0 ]
[ 57002-01-4 ]
C₁₉H₃₀N₂O₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 4010 - 4019

16
[ 64-17-5 ]
[ 57002-01-4 ]
[ 1029604-12-3 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 6922 - 6923

17
[ 869376-31-8 ]
[ 57002-01-4 ]
C₂₅H₃₂OSi [ No CAS ]
C₂₅H₃₂OSi [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 869 - 873

18
[ 57002-01-4 ]
potassium (E)-2-(cyclohexyl)ethylenetrifluoroborate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 3850 - 3851

19
[ 1187833-88-0 ]
[ 57002-01-4 ]
[ 1187834-64-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 6h;Inert atmosphere;	In a dried and purged vessel were added N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5- yl)-1-phenylmethanimine (0.2 g, 0.536 mmol, 1 eq.), <strong>[57002-01-4][(E)-2-cyclohexylvinyl]boronic acid</strong> (0.090 g, 0.58 mmol, 1.1 eq.), Na2CO3 (0.119 g, 1.12 mmol, 2.1 eq.) and Tetrakis(triphenylphosphine)palladium (0.030 g, 0.027 mmol, 0.05 eq.). A mixture of solvent was added toluene/ethanol/water (4/1/1 ) was added and the vessel purged with argon and sealed. The reaction was heated to 9OºC for 6 hrs. After cooling, 10 ml of EtOAc were added and the solids were filtered through a "Celite" plug and washed with EtOAc. The organics were separated, dried over MgSO4 and concentrated. The residue was <n="88"/>purified by chromatography on silica gel to give N-({6-[(E)-2-cyclohexylvinyl]pyridin-2-yl}methoxy)-1-(1- methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.155 g, 68 % yield) as a colorless gum. HPLC/MS : m/z = 403 (M+H) ; logP(HCooH) = 5.05

Reference： [1]Patent: WO2009/115557,2009,A2 .Location in patent: Page/Page column 86-87

20
[ 623-12-1 ]
[ 57002-01-4 ]
[ 104151-26-0 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 4010 - 4017

21
[ 60785-20-8 ]
[ 57002-01-4 ]
[ 1257325-88-4 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 5563 - 5573

22
[ 573-57-9 ]
[ 57002-01-4 ]
[ 1313278-35-1 ]
C₁₈H₂₂O [ No CAS ]

Reference： [1]Synlett,2011,p. 943 - 946

23
[ 19061-36-0 ]
[ 57002-01-4 ]
[ 1313278-41-9 ]
C₂₀H₂₆O [ No CAS ]

Reference： [1]Synlett,2011,p. 943 - 946

24
[ 882746-92-1 ]
[ 57002-01-4 ]
(S)-(η6-5-bromo-8-(Z)-allylnaphthalene)tricarbonylchromium [ No CAS ]
(η6-5,8-((E)-(CHCHC6H11)2C10H6))tricarbonylchromium [ No CAS ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 3739 - 3741

25
[ 1338718-68-5 ]
[ 57002-01-4 ]
(E)-tert-butyl 4-(5-(4-(butyloxycarbonylaminomethyl)piperidin-1-yl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-(2-cyclohexylvinyl)thiazol-5-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 130℃; for 0.75h;Inert atmosphere;	Example 281 5-amino-N-(5-(4-(aminomethyl)piperidin-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-cyclohexylethyl)thiazole-4-carboxamide 281 A mixture of tert-butyl 4-(5-(4-(butyloxycarbonylaminomethyl)piperidin-1-yl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-bromothiazol-5-ylcarbamate (0.203 g, 0.33 mmol), Na2CO3 (70 mg, 0.66 mmol) and <strong>[57002-01-4]trans-(2-cyclohexylvinyl)boronic acid</strong> (0.102 g, 0.66 mmol) in DME (1.5 mL) and water (0.5 mL) was degassed by gently bubbling nitrogen through the mixture for 15 min. [1,1'-Bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (27 mg, 0.033 mmol) was then added and the mixture degassed for a further 10 min before being heated in a microwave at 130 C. for 45 min. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were passed through a phase separator cartridge and concentrated under reduced pressure. The residue was purified via silica gel column chromatography (0-100% EtOAc/isohexane) to afford (E)-tert-butyl 4-(5-(4-(butyloxycarbonylaminomethyl)piperidin-1-yl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-(2-cyclohexylvinyl)thiazol-5-ylcarbamate as a brown gum (0.144 g, 68%).

Reference： [1]Patent: US2011/251176,2011,A1 .Location in patent: Page/Page column 151

26
[ 17084-13-8 ]
[ 1192147-21-9 ]
[ 57002-01-4 ]
(S)-(η5-pentamethylcyclopentadienyl)(η6-5-((E)-2-cyclohexylvinyl)naphthalene)ruthenium(II) hexafluorophosphate [ No CAS ]

Reference： [1]Organometallics,2011,vol. 30,p. 6303 - 6315

27
[ 1361582-80-0 ]
[ 57002-01-4 ]
[ 1361582-46-8 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14366 - 14370

28
[ 1361582-91-3 ]
[ 57002-01-4 ]
[ 1361582-56-0 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14366 - 14370

29
[ 1361582-94-6 ]
[ 57002-01-4 ]
7-((R)-1-(Benzyloxy)propan-2-yl)-5-cyclohexyl-1-tosyl-2,3,4,5-tetrahydro-1H-indole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14366 - 14370

30
[ 1361582-96-8 ]
[ 57002-01-4 ]
5-cyclohexyl-7-((S)-2-methyl-4-((R)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)butyl)-1-tosyl-2,3,4,5-tetrahydro-1H-indole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14366 - 14370

31
[ 1393683-36-7 ]
[ 57002-01-4 ]
[ 1393683-49-2 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 5953 - 5957

32
ethyl 2-(2-tosylhydrazono)propanoate [ No CAS ]
[ 57002-01-4 ]
[ 1393683-45-8 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 5953 - 5957

33
[ 3240-34-4 ]
[ 57002-01-4 ]
[ 2926-30-9 ]
[ 1393725-23-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9090 - 9093

34
[ 57002-01-4 ]
(S,E)-2-(2-cyclohexylvinyl)octan-1-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9090 - 9093

35
[ 57002-01-4 ]
C₁₆H₂₈O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9090 - 9093

36
[ 524-38-9 ]
[ 57002-01-4 ]
[ 1402704-17-9 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7799 - 7803

37
[ 524-38-9 ]
[ 57002-01-4 ]
[ 1402704-56-6 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7799 - 7803

38
[ 300-57-2 ]
[ 57002-01-4 ]
[ 1402076-65-6 ]
C₁₇H₂₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 16496 - 16499,4

39
[ 1493-13-6 ]
[ 31599-59-4 ]
[ 57002-01-4 ]
[ 1428541-22-3 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5332 - 5335

40
[ 55826-65-8 ]
[ 57002-01-4 ]
[ 1436848-91-7 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3582 - 3592

41
[ 57002-01-4 ]
[ 1436847-05-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3582 - 3592

42
[ 57002-01-4 ]
[ 1425511-10-9 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3582 - 3592

43
[ 124-13-0 ]
[ 57002-01-4 ]
2-(3-cyclohexyloxiran-2-yl)octyl-2-napthoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 11756 - 11759

44
[ 124-13-0 ]
[ 57002-01-4 ]
[ 1449245-93-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 11756 - 11759

45
[ 124-13-0 ]
[ 57002-01-4 ]
[ 1005201-81-9 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 11756 - 11759

46
[ 57002-01-4 ]
[ 1448433-78-0 ]

Reference： [1]Patent: WO2013/109991,2013,A1
[2]Patent: US9447078,2016,B2

47
[ 57002-01-4 ]
[ 1448433-81-5 ]

Reference： [1]Patent: WO2013/109991,2013,A1
[2]Patent: US9447078,2016,B2

48
[ 57002-01-4 ]
[ 1448433-80-4 ]

Reference： [1]Patent: WO2013/109991,2013,A1
[2]Patent: US9447078,2016,B2

49
[ 34160-40-2 ]
[ 57002-01-4 ]
[ 1448433-79-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium diacetate; potassium carbonate; triphenylphosphine; In isopropyl alcohol; at 70℃; for 20h;Inert atmosphere;	Step 1 : To an argon saturated mixture of <strong>[57002-01-4](E)-(2-cyclohexylvinyl)boronic acid</strong> (8) (2.74 g, 16.0 mmol), 6-bromopicolinaldehyde (9) (3.0 g, 16 mmol), Pd(OAc)2 (0.04 g, 0.18 mmol), K2C03 (2M in z-PrOH, 30 mmol) was added PPh3 (0.20 g, 0.76 mmol). The reaction mixture was stirred at 70 C for 20 hours under N2, concentrated under reduced pressure and partitioned between H20 (80 ml) and ethyl acetate (80 ml). Organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure. Purification by flash chromatography (30% - 50% EtOAc - hexanes gradient) gave alkene (10) as a pale yellow oil. Yield (3.1 g, 90%); 1H NMR (400 MHz, DMSO-d6) delta 9.34 (s, 1H), 7.93 (t, J= 7.6 Hz, 1H), 7.71 (d, J= 8.4 Hz, 1H), 7.69 (d, J= 8.4 Hz, 1H), 7.86 (dd, J= 6.8, 16.0 Hz, 1H), 6.54 (d, J= 16 Hz, 1H), 2.26-2.16 (m, 1H), 1.84-1.58 (m, 5H), 1.36-1.10 (m, 5H).
90%	With palladium diacetate; potassium carbonate; triphenylphosphine; In isopropyl alcohol; at 70℃; for 20h;Inert atmosphere;	£6L ?(RI ?5) tE6 2 (9p-oswu ?ZRN oot) WIN RT (%o6? FE) PJaA MOJJa( ajUd U SU (01) auajj AU QuatpU1SauUxaJ-oyQ3 %oc-%oE) £qdU1OwwO1qo JSU £q uot-Uogun alnSSald paonpai iapun pawauaouoo UU tOStUNSflO1p(quU laAo paup SUM IaJ(UJ otUU1Q Qw os) arnaop(a UU (jw os) OtR uaaaq pauotpnUd puU alnSSaldpaonpai iapun papmuaouoo tN iapun Srnoq o IOJ D00L U 1fl3S SUM ainjxnu uOl3oUal aj Qowm 9L0 ? oo) Eq SUM (jounu OE ?R01d1 U? w) EQy ?Qoanu810 ? too) t(vo)Pd ?Qoww 91 ? oE) (6) ap(qapJUutJ-OotdOwOlq-9 ?Qoanu 091 ? tLi (5) ptcrn otuOlOqQi(utAp(-xajopi(o-j-() jo ainpctw PW1flJUS UO1U UU oi :1 dais(Rd ?m) 0IU9EI ?(Rd ?w) SdI-tSI ?(RI ?w) 9I9 ?(RI ?ZR 91=1 ?P) td9 ?(RI ?ZR 091 ?89=f ?PP) 98L ?(RI ?ZR T8=1 ?P) 69L ?(RI ?ZR T8=1 ?P) ILL ?(RI ?ZR 9L=f ?1)

Reference： [1]Patent: WO2013/109991,2013,A1 .Location in patent: Paragraph 00347
[2]Patent: US9447078,2016,B2 .Location in patent: Page/Page column 125; 126

50
[ 57002-01-4 ]
[ 174712-01-7 ]
(Z)-3-benzylidene-4-((E)-3-cyclohexylallyl)-1-tosylpyrrolidine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 12212 - 12216

51
[ 574-66-3 ]
[ 57002-01-4 ]
[ 1453804-75-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4830 - 4833

52
[ 367-24-8 ]
[ 57002-01-4 ]
[ 1400654-22-9 ]

Yield	Reaction Conditions	Operation in experiment
2.58 g	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium tert-butylate; In isopropyl alcohol; at 20℃; for 15h;Inert atmosphere;	(1) Isopropanol (60 mL) was added to PEPPSI-IPr catalyst (161 mg, 0.24 mmol) and tert-butoxy potassium (2.65 g, 23.6 mmol) under an argon atmosphere, and the mixture was stirred at room temperature for 15 min. To the reaction mixture were added <strong>[57002-01-4]trans-(2-cyclohexylvinyl)boronic acid</strong> (2.00 g, 13.0 mmol) and 4-bromo-2-fluoroaniline (2.24 g, 11.8 mmol) successively and the mixture was stirred at room temperature for 15 hr. Water was added thereto, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to afford 4-[(E)-2-cyclohexylethenyl]-2-fluoroaniline as a reddish brown oil (2.58 g).

Reference： [1]Patent: EP2687507,2014,A1 .Location in patent: Paragraph 0375

53
[ 61650-22-4 ]
[ 57002-01-4 ]
[ 1613511-03-7 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3444 - 3447

54
[ 55671-55-1 ]
[ 931-48-6 ]
[ 7732-18-5 ]
[ 57002-01-4 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3444 - 3447
[2]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1510 - 1516

55
[ 1374225-73-6 ]
[ 57002-01-4 ]
[ 1620636-46-5 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 7391 - 7398

56
C₁₂H₁₁NO₂S [ No CAS ]
[ 57002-01-4 ]
(E)-4-(2-cyclohexylvinyl)-3-(6-methoxybenzo[d]thiazol-2-yl)-5-methyl-1,2-oxaborol-2(5H)-ol [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1605 - 1608

57
[ 57002-01-4 ]
2-cyclohexyl-1-tosyl-1H-indole [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2748 - 2751

58
[ 57002-01-4 ]
(E)-N-(2-(2-cyclohexylvinyl)phenyl)-4-methylbenzenesulfonamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2748 - 2751

59
[ 57002-01-4 ]
[ 615-36-1 ]
(E)-2-(2-cyclohexylvinyl)aniline [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2748 - 2751

60
4-nitro-N-[(2S)-3-methyl-1-oxobutan-2-yl]benzenesulfonamide [ No CAS ]
[ 57002-01-4 ]
[ 124-02-7 ]
N-((2S,3R,E)-5-cyclohexyl-3-(diallylamino)-1-phenylpent-4-en-2-yl)-4-nitrobenzenesulfonamide [ No CAS ]
N-((2R,3S,E)-5-cyclohexyl-3-(diallylamino)-1-phenylpent-4-en-2-yl)-4-nitrobenzenesulfonamide [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 9991 - 9994
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 1940 - 1951

61
[ 57002-01-4 ]
[ 98495-32-0 ]
C₁₄H₁₉BN₄ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 74 - 77

62
[ 1038998-19-4 ]
[ 57002-01-4 ]
[ 2926-27-4 ]
(E)-(2-cyclohexylvinyl)(2,4,6-triisopropylphenyl)-λ³-iodanyl trifluoromethanesulfonate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7857 - 7861
Angew. Chem.,2015,vol. 127,p. 7968 - 7972

63
[ 19932-85-5 ]
[ 57002-01-4 ]
6-[(E)-2-cyclohexylvinyl]-3H-1,3-benzoxazol-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

64
[ 57002-01-4 ]
6-(2-cyclohexylethyl)-3H-1,3-benzoxazol-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

65
[ 57002-01-4 ]
6-[(E)-2-cyclohexylvinyl]-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

66
[ 57002-01-4 ]
6-(2-cyclohexylethyl)-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

67
[ 55671-55-1 ]
[ 931-48-6 ]
[ 57002-01-4 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15620 - 15623

68
[ 57002-01-4 ]
(R)-4-(2-cyclohexyl-1-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)ethyl)morpholine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15620 - 15623

69
[ 57002-01-4 ]
(R)-2-cyclohexyl-N,N-diethyl-1-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)ethan-1-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15620 - 15623

70
[ 57002-01-4 ]
(R)-N-benzyl-2-cyclohexyl-N-methyl-1-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)ethan-1-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15620 - 15623

71
[ 57002-01-4 ]
[ 479-27-6 ]
[ 1147459-18-4 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15620 - 15623

72
[ 57002-01-4 ]
(R)-6-bromo-4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one [ No CAS ]
(4R)-6-[(E)-2-cyclohexylvinyl]-4-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one [ No CAS ]

Reference： [1]Patent: WO2016/55028,2016,A1 .Location in patent: Page/Page column 103

73
[ 1493-13-6 ]
[ 88-67-5 ]
[ 57002-01-4 ]
(E)-1-(2-cyclohexylvinyl)-2-carboxyphenyliodonium triflate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 16066 - 16070

74
[ 88-67-5 ]
[ 57002-01-4 ]
(E)-1-(2-cyclohexylvinyl)-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%		Following a reported procedure,19 trifluoromethanesulfonic acid (TfOH, 0.533 mL, 6.00 mmol, 1.00equiv.) was added dropwise to a stirred solution of 2-iodobenzoic acid (60) (1.49 g, 6.00 mmol, 1.00equiv.) and meta-chloroperoxybenzoic acid (mCPBA-77%, 1.48 g, 6.60 mmol, 1.10 equiv.) indichloromethane (37.5 mL) at 0 C. After 15 minutes stirring at room temperature, <strong>[57002-01-4](E)-(2-cyclohexylvinyl)boronic acid</strong> (70) (1.85 g, 12.0 mmol, 2.00 equiv.) was added in one portion at 0 C. Thereaction mixture was stirred for an additional 1 hour at room temperature, then the resulting mixture wasconcentrated in vacuo. Diethyl ether (300 mL) was added and the resulting mixture was vigorouslystirred over 30 minutes. The solid was filtered off and washed with portions of diethyl ether (5 x 50 mL).The resulting solid was dissolved in dichloromethane (50 mL) and treated with a solution of saturatedaqueous sodium bicarbonate (50 mL). The mixture was vigorously stirred for 1 hour, then the organiclayer was diluted with dichloromethane (100 mL) and the two layers were separated. The aqueous layerwas extracted with additional portions of dichloromethane (3 x 50 mL) and the combined organic layerswere washed with water (50 mL) and brine (50 mL), then dried over magnesium sulfate and filtered. Thevolatiles were removed to afford pure (E)-1-(2-cyclohexylvinyl)-1,2-benziodoxol-3(1H)-one (1n) (0.654g, 1.84 mmol, 31% yield) as a beige solid.

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 13361 - 13365
Angew. Chem.,2017,vol. 129,p. 13546 - 13550,5
[2]Chem,2019,vol. 5,p. 2243 - 2263
[3]Organic Letters,2020,vol. 22,p. 422 - 427
[4]Chemistry - A European Journal,2016,vol. 22,p. 16066 - 16070

75
[ 610-94-6 ]
[ 57002-01-4 ]
3-cyclohexyl-4-fluoroisochroman-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 13858 - 13861

76
[ 610-94-6 ]
[ 57002-01-4 ]
methyl (E)-2-(2-cyclohexylvinyl)benzoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 13858 - 13861

77
[ 57002-01-4 ]
[ 36155-85-8 ]
[ 1448434-22-7 ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; triphenylphosphine; In isopropyl alcohol; at 70℃; for 20h;Inert atmosphere;	£6L ?(RI ?5) tE6 2 (9p-oswu ?ZRN oot) WIN RT (percento6? FE) PJaA MOJJa( ajUd U SU (01) auajj AU QuatpU1SauUxaJ?oyQ3 percentoc-percentoE) £qdU1OwwO1qo JSU £q uot-Uogun alnSSald paonpai iapun pawauaouoo UU tOStUNSflO1p(quU laAo paup SUM IaJ(UJ otUU1Q Qw os) arnaop(a UU (jw os) OtR uaaaq pauotpnUd puU alnSSaldpaonpai iapun papmuaouoo tN iapun Srnoq o IOJ D00L U 1fl3S SUM ainjxnu uOl3oUal aj Qowm 9L0 ? oo) Eq SUM (jounu OE ?R01d1 U? w) EQy ?Qoanu810 ? too) t(°vo)Pd ?Qoww 91 ? oE) (6) ap(qapJUutJ-OotdOwOlq-9 ?Qoanu 091 ? tLi (5) ptcrn otuOlOqQi(utAp(-xajopi(o-j-() jo ainpctw PW1flJUS UO1U UU oi :1 dais(Rd ?m) 0IU9EI ?(Rd ?w) SdI-tSI ?(RI ?w) 9I9 ?(RI ?ZR 91=1 ?P) td9 ?(RI ?ZR 091 ?89=f ?PP) 98L ?(RI ?ZR T8=1 ?P) 69L ?(RI ?ZR T8=1 ?P) ILL ?(RI ?ZR 9L=f ?1) Step 1: Coupling of <strong>[57002-01-4](E)-(2-cyclohexylvinyl)boronic acid</strong> with 5-chlorothiophene-3-carbaldehyde in the presence of tetrabutylamonium bromide (1.2 g, 3.72 mmol) following the method used in Example 3 gave after flash chromatography purification (10percent-50percent EtOAc-hexanes gradient) (E)-5-(2-cyclohexylvinyl)thiophene-3-carbaldehyde as a yellow oil. Yield (0.4 g, 53percent); 1H NMR (400 MHz, DMSO-d6) delta 9.77 (s, 1H), 8.38 (s, 1H), 7.29 (s, 1H), 6.55 (d, J=8.0 Hz, 1H), 6.13 (dd, J=16.4, 6.8 Hz, 1H), 2.08-2.02 (m, 1H), 1.80-1.58 (m, 5H), 1.38-1.08 (m, 5H).

Reference： [1]Patent: US9447078,2016,B2 .Location in patent: Page/Page column 125; 126; 139

78
[ 57002-01-4 ]
N'-(5-cyanopentaN-2-ylidene)-4-methylbenzenesulfonohydrazide [ No CAS ]
(E)-2-(2-cyclohexylvinyl)-2-methylcyclopentan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12061 - 12064

79
[ 57002-01-4 ]
[ 13992-91-1 ]
rac-(3aS,7aS)-7a-((E)-2-cyclohexylvinyl)octahydro-1H-inden-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 12061 - 12064

80
[ 57002-01-4 ]
angiotensin I [ No CAS ]
C₇₀H₁₀₁N₁₇O₁₄ [ No CAS ]