[ CAS No. 16156-50-6 ] {[proInfo.proName]}

Name: 16156-50-6|Hexyl methanesulfonate|97%
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SKU: A129136
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Quality Control of [ 16156-50-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 16156-50-6 ]

Product Details of [ 16156-50-6 ]

CAS No. :	16156-50-6	MDL No. :	MFCD00674707
Formula :	C₇H₁₆O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	URIRDRHUUFRHAS-UHFFFAOYSA-N
M.W :	180.27	Pubchem ID :	12517373
Synonyms :

Calculated chemistry of [ 16156-50-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	6
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.81
TPSA :	51.75 Å²

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) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	1.98
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	1.45
Log Po/w (SILICOS-IT) :	0.98
Consensus Log Po/w :	1.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.81
Solubility :	2.8 mg/ml ; 0.0155 mol/l
Class :	Very soluble
Log S (Ali) :	-2.69
Solubility :	0.366 mg/ml ; 0.00203 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.34
Solubility :	0.818 mg/ml ; 0.00454 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.7

Safety of [ 16156-50-6 ]

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 [ 16156-50-6 ]

* 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 [ 16156-50-6 ]
Downstream synthetic route of [ 16156-50-6 ]

[ 16156-50-6 ] Synthesis Path-Upstream 1~4

1
[ 124-63-0 ]
[ 111-27-3 ]
[ 16156-50-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In dichloromethane at 0 - 20℃;	General procedure: Alcohols (50 mmol, 1 equiv.) and 11.08 mL Et3N (80 mmol, 1.6 equiv.) was dissolved in 60 mL CH2Cl2, and the solution was cooleddown to 0 °C, then 4.33 mL methanesulfonyl chloride (56 mmol, 1.12 equiv.) was introduced by syringe successively. The mixture is stirredfor 30 min at 0 °C, and then stirred overnight at room temperature. The organic layer is washed successively with 1M hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and brine. The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by column chromatography with silica gel (EtOAc: petroleum=1: 2).

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7753 - 7759
[2] Journal of the American Chemical Society, 1985, vol. 107, # 18, p. 5210 - 5219
[3] Journal of Fluorine Chemistry, 2018, vol. 214, p. 35 - 41
[4] Journal of the Electrochemical Society, 2010, vol. 157, # 9, p. F124-F129
[5] European Journal of Organic Chemistry, 2018, vol. 2018, # 35, p. 4850 - 4856
[6] Canadian Journal of Chemistry, 1956, vol. 34, p. 757,760
[7] Journal of the American Chemical Society, 1954, vol. 76, p. 2984,2986
[8] Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2807 - 2813
[9] Tetrahedron Letters, 1990, vol. 31, # 17, p. 2457 - 2460
[10] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 8, p. 1201 - 1208
[11] Synthetic Communications, 1984, vol. 14, # 5, p. 469 - 476
[12] Green Chemistry, 2009, vol. 11, # 12, p. 1955 - 1960
[13] Physical Chemistry Chemical Physics, 2009, vol. 11, # 39, p. 8939 - 8948
[14] Catalysis Communications, 2010, vol. 11, # 5, p. 470 - 475
[15] Tetrahedron Letters, 2017, vol. 58, # 1, p. 59 - 62

2
[ 75-75-2 ]
[ 16156-50-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	at 20℃; Inert atmosphere	General procedure: Procedure A: To a solution of the sulfonic acid (0.164 mmol) in methylene chloride (1.5 mL) was added a 0.4M solution of 1 in methylene chloride dropwise (0.2 mL, 0.082 mmol). The reaction mixture was stirred under argon overnight and then concentrated under reduced pressure at room temperature. The residue was suspended in ether, washed with saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure to yield the sulfonic esters below.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 28, p. 2700 - 2702

3
[ 65411-49-6 ]
[ 638-45-9 ]
[ 544-10-5 ]
[ 16156-50-6 ]

Reference： [1] Journal of Organic Chemistry, 1985, vol. 50, # 11, p. 1872 - 1876

4
[ 111-25-1 ]
[ 16156-50-6 ]

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 28, p. 2700 - 2702

[ 16156-50-6 ] Synthesis Path-Downstream 1~84

1
[ 16156-50-6 ]
[ 333-20-0 ]
[ 6803-40-3 ]

Reference： [1]Canadian Journal of Chemistry,1956,vol. 34,p. 757,760
[2]Canadian Journal of Chemistry,1956,vol. 34,p. 757,760

2
[ 16156-50-6 ]
[ 373-14-8 ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 59 - 62
[2]Canadian Journal of Chemistry,1956,vol. 34,p. 757,760

3
[ 16156-50-6 ]
[ 4312-76-9 ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 13073 - 13091
[2]Journal of the American Chemical Society,1954,vol. 76,p. 2984,2986

4
[ 16156-50-6 ]
[ 3903-89-7 ]

Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 5210 - 5219
[2]Journal of the American Chemical Society,1955,vol. 77,p. 551,552,553

5
[ 124-63-0 ]
[ 111-27-3 ]
[ 16156-50-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In dichloromethane; at 0 - 20℃;	General procedure: Alcohols (50 mmol, 1 equiv.) and 11.08 mL Et3N (80 mmol, 1.6 equiv.) was dissolved in 60 mL CH2Cl2, and the solution was cooleddown to 0 C, then 4.33 mL methanesulfonyl chloride (56 mmol, 1.12 equiv.) was introduced by syringe successively. The mixture is stirredfor 30 min at 0 C, and then stirred overnight at room temperature. The organic layer is washed successively with 1M hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and brine. The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by column chromatography with silica gel (EtOAc: petroleum=1: 2).
88.1%	With triethylamine; In dichloromethane; at 10℃; for 3h;Large scale;	1-hexanol (1.2 kg, 11.70 mol), triethylamine (2.4 kg, 23.40 mol),Stir methylene chloride (12.0 L),MsCl (1.6 kg, 14.0 mol) was added dropwise while maintaining an internal temperature of 10 C. or less.After completion of the dropwise addition, the internal temperature was maintained at 10 C. or lower and stirred for 3 hours.After layer separation by adding 5 L of purified water, the separated organic layer was concentrated under reduced pressure to obtain the title compound (1.9 kg, 88.1%).
	With triethylamine; In dichloromethane; for 2h;	General procedure: In a 50 mL round-bottomed flask, 3-phenylpropan-1-ol (0.136 ml 1 mmol) and triethylamine (0.140 ml, 3 mmol) were added to DCM (25 ml). The methanesulfonyl chloride (0.090 ml, 1.2 mmol) was added slowly and allowed to stir for 2 hours, After the completion of reaction, Add water and reaction mixture was extracted with DCM. Organic layer washed with brine and dried over Na2SO4 and concentrated in vacuo. The title compound was isolated using column chromatography (0-20% EtOAc: hexane) gave 0.192 mg 90% colorless oil.

With pyridine; at 0 - 20℃; for 24h;

General procedure: The synthesis of the AKGs was performed following the literature with some modifications (Baumann and Mangold 1964; Hanus et al. 2001; Appendino et al. 2003; Parkkari et al. 2006). LiAlH4 (550 mg, 14.5 mmol) was added slowly to a solution of the corresponding methyl ester (3.4 mmol) in anhydrous tetrahydrofuran (15 mL) at 0C and stirred for 1 h and was then left at 20C for 20 h. The reaction mixture was washed with NaOH (10%) followed by HCl (10%) and extracted with diethyl ether (3 × 20 mL); the extract was neutralized with saturated NaHCO3, dried under reduced pressure and purified by CC. The alcohol obtained was subsequently mesylated in absolute pyridine (4.5 mL, 55.6 mmol) at 0C by the addition of MsCl (880 mg, 7.65 mmol) and the solution was maintained for 24 h at 20C. After quenching the reaction with 5 mL of degasified water, the solution was extracted with diethyl ether (4 × 20 mL). The organic phase was washed with H2SO4 (2 N), neutralized, concentrated in vacuo, and the crude mesylate was purified by CC. KOH (127 mg, 2.26 mmol) was added to the chiral precursor (R)-solketal (283 mg, 2.14 mmol) in anhydrous toluene (2 mL). The reaction stirred at 50C for 1 h before the addition of metallic Na (3 mg, 0.15 mmol) followed by the mesylate dissolved in toluene (15 mL), and the resulting mixture was kept at 50C for 72 h. The reaction was quenched with HCl (10%) and extracted with ethyl ether (4 × 20 mL). The organic phase was neutralized, concentrated and purified by CC to give 1-O-alkyl-2,3-O-isopropylidene-sn-glycerol. This intermediate was deprotected in 5 mL of HCl:MeOH (1:10 v/v) and refluxed overnight. After the addition of H2O (10 mL) and extraction with diethyl ether (4 × 20 mL), the organic phase was neutralized, evaporatedto dryness in vacuo, and the residue was purified by CC to afford pure AKGs. Each step in the synthesis was monitored by TLC, and all CC steps were eluted with hexane-toluene-ethyl acetate (10:0:0-0:10:0-0:0:10) mixtures. The structures of the synthesised compounds were confirmed by 1H, 13C APT NMR with COSY, HMQC, HMBC and ESI-MS or HRESI-MS spectra along with the specific optical rotation.

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7753 - 7759
[2]Journal of the American Chemical Society,1985,vol. 107,p. 5210 - 5219
[3]Journal of Fluorine Chemistry,2018,vol. 214,p. 35 - 41
[4]Journal of the Electrochemical Society,2010,vol. 157,p. F124-F129
[5]Patent: KR2020/2720,2020,A .Location in patent: Paragraph 0077-0079
[6]European Journal of Organic Chemistry,2018,vol. 2018,p. 4850 - 4856
[7]Canadian Journal of Chemistry,1956,vol. 34,p. 757,760
[8]Journal of Medicinal Chemistry,1990,vol. 33,p. 2807 - 2813
[9]Tetrahedron Letters,1990,vol. 31,p. 2457 - 2460
[10]Journal of the Chemical Society. Perkin transactions II,1991,p. 1201 - 1208
[11]Synthetic Communications,1984,vol. 14,p. 469 - 476
[12]Green Chemistry,2009,vol. 11,p. 1955 - 1960
[13]Physical Chemistry Chemical Physics,2009,vol. 11,p. 8939 - 8948
[14]Catalysis Communications,2010,vol. 11,p. 470 - 475
[15]Tetrahedron Letters,2017,vol. 58,p. 59 - 62
[16]Natural Product Research,2019

6
[ 16156-50-6 ]
[ 94903-79-4 ]
[1α,2α(Z),3α,4α]-7-[3-[(Hexyloxy)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, hexyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

7
[ 16156-50-6 ]
[ 128578-16-5 ]
[ 128577-70-8 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2807 - 2813

8
[ 16156-50-6 ]
diisobutylaluminum benzenetellurolate [ No CAS ]
[ 85055-59-0 ]

Reference： [1]Chemistry Letters,1991,p. 415 - 418
[2]Chemistry Letters,1991,p. 415 - 418

9
[ 16156-50-6 ]
[ 104596-12-5 ]
(Z)-7-((1R,2S,3R,4S)-3-Hexyloxymethyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid hexyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

10
[ 16156-50-6 ]
[ 104596-11-4 ]
(Z)-7-((1S,2S,3S,4R)-3-Hexyloxymethyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid hexyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

11
[ 16156-50-6 ]
[ 104596-13-6 ]
(Z)-7-((1S,2S,3R,4R)-3-Hexyloxymethyl-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid hexyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

12
[ 16156-50-6 ]
[ 76031-50-0 ]
[ 73735-27-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1943 - 1947

13
[ 16156-50-6 ]
(Z)-7-[(1R,2S,3S,4S)-3-(1-Hydroxy-ethyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester [ No CAS ]
(Z)-7-[(1S,2R,3R,4R)-3-(1-Hexyloxy-ethyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid hexyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

14
[ 16156-50-6 ]
[ 592-41-6 ]
[ 75-75-2 ]

Reference： [1]Journal of Physical Chemistry,1989,vol. 93,p. 201 - 202

15
[ 16156-50-6 ]
[ 4853-80-9 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 2457 - 2460

16
[ 16156-50-6 ]
[ 638-45-9 ]

Reference： [1]Synthetic Communications,1984,vol. 14,p. 469 - 476

17
[ 65411-49-6 ]
[ 638-45-9 ]
[ 544-10-5 ]
[ 16156-50-6 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 1872 - 1876

18
[ 16156-50-6 ]
[ 80-97-7 ]
(3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-hexyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1994,vol. 250,p. 73 - 84

19
[ 16156-50-6 ]
[ 148528-45-4 ]
[ 169616-10-8 ]

Reference： [1]Synthesis,1995,p. 795 - 800

20
[ 16156-50-6 ]
[ 50-81-7 ]
3-O-hexyl-L-ascorbic acid [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 357 - 361

Yield	Reaction Conditions	Operation in experiment
		Examples of the sulfonic acid ester of the formula (V') include the following: ... propyl methanesulfonate, isopropyl methanesulfonate, butyl methanesulfonate, pentyl methanesulfonate, hexyl methanesulfonate, heptyl methanesulfonate, octyl methanesulfonate, nonyl methanesulfonate, and ...

23
1-hexyl-3-methylimidazolium azide [ No CAS ]
[ 16156-50-6 ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]
[ 6926-45-0 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3961 - 3963
[2]Tetrahedron,2008,vol. 64,p. 1689 - 1695

24
[ 847499-74-5 ]
[ 16156-50-6 ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]
[ 6803-40-3 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3961 - 3963
[2]Tetrahedron,2008,vol. 64,p. 1689 - 1695

25
1-hexyl-3-methylimidazolium 4-nitrophenoxide [ No CAS ]
[ 16156-50-6 ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]
[ 15440-98-9 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3961 - 3963
[2]Tetrahedron,2008,vol. 64,p. 1689 - 1695

26
[ 16156-50-6 ]
[ 85100-78-3 ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]
[ 111-25-1 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3961 - 3963
[2]Tetrahedron,2008,vol. 64,p. 1689 - 1695

27
[ 16156-50-6 ]
[ 171058-17-6 ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]
[ 544-10-5 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3961 - 3963
[2]Tetrahedron,2008,vol. 64,p. 1689 - 1695

28
[ 16156-50-6 ]
1-n-hexyl-3-methylimidazolium iodide [ No CAS ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]
[ 638-45-9 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3961 - 3963
[2]Tetrahedron,2008,vol. 64,p. 1689 - 1695

29
[ 616-47-7 ]
[ 16156-50-6 ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 1834 - 1841
[2]Journal of the Electrochemical Society,2010,vol. 157,p. F124-F129
[3]Physical Chemistry Chemical Physics,2009,vol. 11,p. 8939 - 8948
[4]Green Chemistry,2009,vol. 11,p. 1955 - 1960

30
[ 16156-50-6 ]
<1β,2α(Z),3α,4β>-7-<3-<1-(hexyloxy)ethyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

31
[ 16156-50-6 ]
<1R-<1α,2β(Z),3β,4α>>-7-<3-(methoxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

32
[ 16156-50-6 ]
<1R-<1α,2β(Z),3β,4α>>-7-<3-<(hexyloxy)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

33
[ 16156-50-6 ]
<1β,2β(Z),3α,4β>-7-<3-<(hexyloxy)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

34
[ 16156-50-6 ]
<1β,2α(Z),3β,4β>-7-<3-<(hexyloxy)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

35
[ 16156-50-6 ]
<1α,2α(Z),3α,4α>-7-<3-<(hexyloxy)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

36
[ 16156-50-6 ]
[ 7018-92-0 ]

Reference： [1]Synthetic Communications,1984,vol. 14,p. 469 - 476

37
[ 16156-50-6 ]
[ 1128-08-1 ]

Reference： [1]Synthetic Communications,1984,vol. 14,p. 469 - 476

38
[ 16156-50-6 ]
[ 92596-21-9 ]

Reference： [1]Synthetic Communications,1984,vol. 14,p. 469 - 476

39
[ 16156-50-6 ]
[ 92596-24-2 ]

Reference： [1]Synthetic Communications,1984,vol. 14,p. 469 - 476

40
[ 16156-50-6 ]
[ 128577-95-7 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2807 - 2813

41
[ 16156-50-6 ]
[ 70145-04-9 ]
[1β,2α(5Z),3α,4β]-7-[3-[(hexyloxy)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, hexyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
390 mg (83%)	With potassium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; hexane;	B. [1beta,2alpha(5Z),3alpha,4beta]-7-[3-[(Hexyloxy)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, hexyl ester A suspension of 0.56 g of powdered KOH in 15 ml of dry xylene was heated to reflux and 7 ml of xylene was distilled off. To this mixture was added a solution of 300 mg (1.12 mmol) of alcohol ester from part A in 10 ml of dry xylene. The resulting mixture was heated to reflux and 9 ml of xylene was distilled off. To this mixture was added 1.0 g (5.6 mmol) of n-hexylmethanesulfonate and the resulting mixture was heated at reflux for 11/2 hours. The reaction mixture was cooled to ambient temperature and diluted with CH2 Cl2 (60 ml). The resulting solution was poured into 50 ml saturated NaHCO3. The layers were separated and the aqueous phase was extracted (2*60 ml) with CH2 Cl2. The combined CH2 Cl2 extracts were dried over MgSO4, then concentrated in vacuo to yield 0.9 g of crude product. The crude product was chromatographed on 33.4 g of silica gel 60 with hexane:ether (5:1) to yield 390 mg (83%) of the title hexyl ester.

Reference： [1]Patent: US4582854,1986,A

42
[ 16156-50-6 ]
[ 60586-80-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene;	To a solution of 103 mg of powered potassium hydroxide (2.5 mmole, 10 eq.) in 10 ml of dry xylene was added a solution of 70 mg of title J alcohol (0.25 mmole) in 10 ml of dry xylene. The mixture was heated to reflux and 10 ml of xylene was distilled off. To the cooled remaining solution was added 405 mg of <strong>[16156-50-6]hexyl mesylate</strong> (2.5 mmole, 10 eq.). The mixture was refluxed for 2 hours, then cooled to 25 C. and diluted with 100 ml of ether. The ethereal solution was washed with two 30 ml portions of H2 O, dried over anhydrous MgSO4 and concentrated. The residue was purified on a silica gel column, eluding with 15% EtOAc/hexane to give 110 mg of a mixture of title ether and hexylmesylate.

Reference： [1]Patent: US4536513,1985,A

43
[ 1739-84-0 ]
[ 16156-50-6 ]
[ 898256-64-9 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 1689 - 1695

44
[ 1007398-53-9 ]
[ 16156-50-6 ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]
[ 5421-17-0 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 1689 - 1695

45
[ 16156-50-6 ]
1-hexyl-3-methyl-imidazolium benzoate [ No CAS ]
1-hexyl-3-methylimidazolium methanesulfonate [ No CAS ]
[ 6789-88-4 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 1689 - 1695

46
[ 193142-10-8 ]
[ 16156-50-6 ]
[ 702701-72-2 ]

Yield	Reaction Conditions	Operation in experiment
		A phosgene solution (15 mL of a 20% phosgene in toluene) was cooled to -10 C. and 6 (1.60 g, 3.9 mmol) dissolved in toluene (5 mL) was added dropwise. The reaction was stirred at -10 C. for 0.5 h and then 4 h at RT. The phosgene and toluene was then distilled off and the resultant oil was dried under vacuum to afford 7 a yellowish oil.

Reference： [1]Patent: US2008/207505,2008,A1 .Location in patent: Page/Page column 33

47
[ 16156-50-6 ]
[ 423763-19-3 ]
[ 702701-71-1 ]

Yield	Reaction Conditions	Operation in experiment
36%		To a solution of 3 (5.45 g, 0.13 mol) in tetrahydrofuran (160 mL) was added potassium tert-butoxide (1.60 g, 0.0144 mol) and the reaction was stirred for 1.5 h. Then 4 (2.59 g, 0.0144 mol) dissolved in tetrahydrofuran (20 mL) was added dropwise and the reaction was stirred overnight. The crude reaction was filtered through Celite, washed CH2Cl2, and evaporated to dryness. The resultant oil was dissolved in ethyl acetate (150 mL), washed H2O (2×150 mL), dried MgSO4, and evaporated to dryness. Column chromatography (silica, ethyl acetate) afforded 5 a yellowish oil (2.40 g, 36% yield).

Reference： [1]Patent: US2008/207505,2008,A1 .Location in patent: Page/Page column 32

48
[ 16156-50-6 ]
[ 702701-71-1 ]
[ 193142-10-8 ]

Yield	Reaction Conditions	Operation in experiment
82%		To a solution of 5 (2.4 g, 4.8 mmol) in ethyl acetate (16 mL) was added palladium on activated carbon 10 wt % (1.0 g) and the reaction vessel sealed with a septum. A balloon containing H2 was then inserted in the septum via needle and the reaction was stirred overnight at RT. Crude reaction mixture was filtered through Celite, washed ethyl acetate, and evaporated to dryness to afford 6 a clear oil (1.61 g, 82% yield).

Reference： [1]Patent: US2008/207505,2008,A1 .Location in patent: Page/Page column 32

49
[ 16156-50-6 ]
[ 924638-97-1 ]
[ 1006900-66-8 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 733 - 735

50
[ 288-32-4 ]
[ 16156-50-6 ]
[ 33529-01-0 ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 1955 - 1960
[2]Catalysis Communications,2010,vol. 11,p. 470 - 475

51
[ 16563-14-7 ]
[ 16156-50-6 ]
[ 1276689-05-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1762 - 1765

52
[ 16156-50-6 ]
[ 1276689-07-6 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1762 - 1765

53
[ 16156-50-6 ]
[ 1276689-09-8 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1762 - 1765

54
[ 16156-50-6 ]
[ 1276689-14-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1762 - 1765

55
[ 16156-50-6 ]
[ 6926-45-0 ]

Reference： [1]Organic Preparations and Procedures International,2011,vol. 43,p. 348 - 353

56
[ 1131-16-4 ]
[ 16156-50-6 ]
1-phenyl-3,5-dimethyl-2-hexylpyrazolium methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In acetonitrile; at 80℃;Reflux; Microwave irradiation;	General procedure: 3,5-Dimethyl-1-phenyl-1H-pyrazole (5.0 mmol), appropriate alkylmethanesulfonate (5.0 mmol), and acetonitrile (5.0 mL) were addedto a round-bottomed flask equippedwith a reflux condenser and heatedat 80 C under MWirradiation. The progress of the reaction was monitoredby TLC (80% EtOAc-hexane). After completion of the reaction, acetonitrilewas removed by rotary evaporation. The resulting productwaswashed two times with 20.0 mL of hexane and then two times with20.0 mL of diethylether. After this, active charcoal and 20.0 mL acetonitrilewere added and stirred for 24 h and then filtered. The filtrate wasdried over anhydrous sodiumsulfate and concentrated. The synthesizedsalts were set under vacuum for 48 h at 75 C.

Reference： [1]Journal of Molecular Liquids,2014,vol. 200,p. 129 - 135

57
[ 111-25-1 ]
[ 16156-50-6 ]

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2700 - 2702

58
[ 75-75-2 ]
(E)-1,3-diethyl-2-(hexyltriaz-2-en-1-ylidene)-2,3-dihydro-1H-imidazole [ No CAS ]
[ 16156-50-6 ]
C₇H₁₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In dichloromethane; at 20℃;Inert atmosphere;	General procedure: Procedure A: To a solution of the sulfonic acid (0.164 mmol) in methylene chloride (1.5 mL) was added a 0.4M solution of 1 in methylene chloride dropwise (0.2 mL, 0.082 mmol). The reaction mixture was stirred under argon overnight and then concentrated under reduced pressure at room temperature. The residue was suspended in ether, washed with saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure to yield the sulfonic esters below.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2700 - 2702

59
[ 16156-50-6 ]
N-(2-(dimethylamino)ethyl)-4,4,5,5,6,6,6-heptafluoro-N-hexyl-3,3-bis(trifluoromethyl)hexanamide [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2018,vol. 214,p. 35 - 41

60
[ 16156-50-6 ]
2-(tert-butoxy)-N-(2-(4,4,5,5,6,6,6-heptafluoro-N-hexyl-3,3-bis(trifluoromethyl)hexanamido)ethyl)-N,N-dimethyl-2-oxoethanaminium bromide [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2018,vol. 214,p. 35 - 41

61
[ 16156-50-6 ]
2-((2-(4,4,5,5,6,6,6-heptafluoro-N-hexyl-3,3-bis(trifluoromethyl)hexanamido)ethyl)dimethylammonio)acetate [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2018,vol. 214,p. 35 - 41

62
[ 16156-50-6 ]
[ 108-00-9 ]
N₁-hexyl-N₂,N₂-dimethylethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In acetonitrile; at 0 - 20℃; for 17.25h;	General procedure: Compound 4a-d (2.0 mmol, 1.0 equiv.) in 5 mL MeCN was added to a solution of 0.94 mL N,N-dimethyl-1,2-ethanediamine (10 mmol, 5.0 equiv.) and 0.4 mL triethylamine (3.0 mmol, 1.5 equiv.) in 10 mL MeCN at 0 C during 15 min. The resulting mixture was stirred at room temperature for 17 h. All MeCN was removed under reduced pressure, after this the solution was alkalized to pH=8-9 with 1M NaOH to regenerate the amine and extracted with DCM from H2O. The organic extracts were then washed with brine and dried over Na2SO4, filtered and concentrated. The product was purified by flash column chromatography with neutral aluminum oxide (DCM: MeOH=20: 1).

Reference： [1]Journal of Fluorine Chemistry,2018,vol. 214,p. 35 - 41

63
[ 16156-50-6 ]
5-ethyl-4-methyl-1-hexyl-1,2,3-triazole [ No CAS ]
[ 90076-65-6 ]
4-ethyl-5-methyl-1,3-dihexyl-1,2,3-triazolium bis(trifluoromethylsulfonyl)imide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 4850 - 4856

64
[ 16156-50-6 ]
[ 2307-12-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7753 - 7759

65
[ 16156-50-6 ]
[ 434942-20-8 ]
2,4,6-tris[4-(hexyloxy)-2-hydroxy-3-methylphenyl]-1,3,5-triazine [ No CAS ]