[ CAS No. 6938-66-5 ] {[proInfo.proName]}

Name: 6938-66-5|1-Bromodocosane|95%
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Quality Control of [ 6938-66-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6938-66-5 ]

Product Details of [ 6938-66-5 ]

CAS No. :	6938-66-5	MDL No. :	MFCD00013543
Formula :	C₂₂H₄₅Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QYOXLKAKUAASNA-UHFFFAOYSA-N
M.W :	389.50	Pubchem ID :	81355
Synonyms :

Calculated chemistry of [ 6938-66-5 ]

Physicochemical Properties

Num. heavy atoms :	23
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	20
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	115.74
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	0.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	6.26
Log Po/w (XLOGP3) :	12.47
Log Po/w (WLOGP) :	9.2
Log Po/w (MLOGP) :	7.23
Log Po/w (SILICOS-IT) :	9.46
Consensus Log Po/w :	8.92

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-8.79
Solubility :	0.00000063 mg/ml ; 0.0000000016 mol/l
Class :	Poorly soluble
Log S (Ali) :	-12.49
Solubility :	0.0000000001 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-9.55
Solubility :	0.00000011 mg/ml ; 0.0000000003 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.89

Safety of [ 6938-66-5 ]

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 [ 6938-66-5 ]

* 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 [ 6938-66-5 ]
Downstream synthetic route of [ 6938-66-5 ]

[ 6938-66-5 ] Synthesis Path-Upstream 1~4

1
[ 661-19-8 ]
[ 6938-66-5 ]

Reference： [1] RSC Advances, 2016, vol. 6, # 91, p. 88820 - 88825
[2] Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 497,500
[3] Transactions of the Faraday Society, 1955, vol. 51, p. 1661,1665
[4] Justus Liebigs Annalen der Chemie, 1929, vol. 472, p. 131
[5] Journal of pharmaceutical sciences, 1969, vol. 58, # 10, p. 1228 - 1232
[6] Bulletin of the Chemical Society of Japan, 1960, vol. 33, p. 531 - 534
[7] Journal of Organic Chemistry, 1965, vol. 30, p. 1450 - 1453
[8] RSC Advances, 2016, vol. 6, # 73, p. 69277 - 69281

2
[ 859314-31-1 ]
[ 6938-66-5 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1955, p. 991,993

3
[ 856360-31-1 ]
[ 6938-66-5 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1955, p. 991,993

4
[ 92206-73-0 ]
[ 6938-66-5 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1955, p. 991,993

[ 6938-66-5 ] Synthesis Path-Downstream 1~66

1
[ 661-19-8 ]
[ 6938-66-5 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 88820 - 88825
[2]Chemical Communications,2019,vol. 55,p. 7962 - 7965
[3]Collection of Czechoslovak Chemical Communications,1958,vol. 23,p. 497,500
[4]Justus Liebigs Annalen der Chemie,1929,vol. 472,p. 131
[5]Journal of Pharmaceutical Sciences,1969,vol. 58,p. 1228 - 1232
[6]Bulletin of the Chemical Society of Japan,1960,vol. 33,p. 531 - 534
[7]Journal of Organic Chemistry,1965,vol. 30,p. 1450 - 1453
[8]RSC Advances,2016,vol. 6,p. 69277 - 69281

2
[ 6938-66-5 ]
[ 124-40-3 ]
[ 21542-96-1 ]

Reference： [1]Mendeleev Communications,2007,vol. 17,p. 82 - 84
[2]Chemische Berichte,1940,vol. 73,p. 1419
[3]Journal of Organic Chemistry,1961,vol. 26,p. 4520 - 4522
[4]Journal of the American Chemical Society,2001,vol. 123,p. 5614 - 5615

3
[ 67-56-1 ]
[ 6938-66-5 ]
[ 19102-90-0 ]

Yield	Reaction Conditions	Operation in experiment
	(i) (enzymatic oxidation), (ii) /BRN= 1098229/; Multistep reaction;

Reference： [1]Jones; Howe [Journal of the Chemical Society. Perkin transactions I, 1968, vol. 22, p. 2816 - 2821]

4
2-<(docosyloxy)sulfonyl>-N,N,N-trimethylethanaminium fluorosulfate [ No CAS ]
[ 6938-66-5 ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 7108
[2]Journal of the American Chemical Society,1978,vol. 100,p. 1637 - 1639

5
[ 2615-15-8 ]
[ 6938-66-5 ]
[ 72659-44-0 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 1095 - 1098

6
[ 6938-66-5 ]
[ 1074-82-4 ]
[ 107513-47-3 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 88820 - 88825
[2]Liebigs Annalen der Chemie,1994,p. 465 - 470

7
[ 6938-66-5 ]
[ 112-24-3 ]
[ 137203-77-1 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 112 - 118
[2]Patent: US5494935,1996,A
[3]Patent: US2006/30619,2006,A1 .Location in patent: Page/Page column 11

8
[ 6938-66-5 ]
[ 1068-90-2 ]
[ 162357-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In ethanol;	(1) Diethyl 2-acetamidomalonate (3.0 g) was dissolved in 50 ml of dry ethanol and 1.3 g of sodium ethoxide was added thereto. A solution of 6.5 g of docosyl bromide in 20 ml of dry ethanol was added thereto while stirring at room temperature. The inside of the reaction vessel was displaced with nitrogen and the mixture was refluxed for about 15 hours. The mixture was neutralized with a 1N aqueous hydrochloric acid solution and concentrated. The concentrate was purified by silica gel column chromatography to give 4.2 g of diethyl 2-acetamido-2-docosylmalonate. melting point=79-80 C. IR(KBr): 3300, 2925, 2860, 1750, 1655, 1520, 1220 cm-1

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4451 - 4459
[2]Patent: US5604229,1997,A

9
[ 6938-66-5 ]
[ 150458-04-1 ]
1-(9-Docosyl-9H-xanthen-9-yl)-1H-benzotriazole [ No CAS ]

Reference： [1]Heterocycles,1997,vol. 45,p. 2413 - 2423

10
[ 6938-66-5 ]
n-didocosyl sulfide [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 20081 - 20089
[2]Journal of Physical Chemistry B,2002,vol. 106,p. 593 - 598

11
[ 6938-66-5 ]
[ 767-00-0 ]
4-cyano-1-docosanoxybenzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 12458 - 12465

12
[ 6938-66-5 ]
[ 2150-44-9 ]
[ 545389-66-0 ]

Yield	Reaction Conditions	Operation in experiment
96.5%	With potassium carbonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;	(1) Synthesis of methyl [3,5-bis(docosyloxy)]benzoate Potassium carbonate (19.9 g, 144 mmol) was suspended in dehydrating N,N-dimethylformamide (200 mL), <strong>[6938-66-5]1-bromodocosane</strong> (15.6 g, 46.7 mmol) and methyl (3,5-dihydroxy)benzoate (3.60 g, 21.4 mmol) were added, and the mixture was stirred at 90 C. overnight. After completion of the reaction, the reaction mixture was poured into purified water (800 mL), the mixture was stirred for 1 hr, and the precipitated solid was collected by filtration. The obtained solid was dissolved again in dichloromethane (800 mL), and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and acetone was added again to precipitate a solid. The solid was collected by filtration and slurry-washed in methanol. After filtration, the obtained solid was dried under reduced pressure to give the title compound (13.9 g, 96.5%) as a white solid.
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 16h;Inert atmosphere;	Under an argon atmosphere, potassium carbonate (20.0 g, 145 mmol), methyl 3,5-dihydroxybenzoate (3.60 g, 21.4 mmol), <strong>[6938-66-5]1-bromodocosane</strong> (17.9 g, 46.0 mmol) were dissolved in N,N-dimethylformamide (200 mL), and the mixture was stirred at 70 C. for 16 hr. Completion of the reaction was confirmed by thin layer chromatography, the reaction solution was poured into water (1.00 L) to allow for precipitation to give a solid. The obtained solid was dissolved in dichloromethane (500 mL), and the solid was precipitated with methanol (400 mL), collect by filtration, and dried to give the object compound (16.1 g, yield 96%). 1H-NMR (400 MHz, CDCl3): delta=0.88 (t, 6H, J=6.6 Hz, -CH3), 1.25-1.55 (m, 76H, -OCH2CH2 (CH2)19CH3), 1.77 (m, 4H, -OCH2CH2(CH2)19CH3), 3.89 (s, 3H, C(O)O-CH3), 3.96 (t, 4H, J=6.6 Hz, -OCH2CH2(CH2)19CH3), 6.63 (s, 1H, Ar-H), 7.15 (s, 2H, Ar-H)
23.8 g		To methyl 3,5-dihydroxybenzoate (5.0 g) and potassium carbonate (41.5 g), 1,3-dimethyl-2-imidazolidinone(100 mL) was added, and the mixture was stirred at 80C for 30 minutes. <strong>[6938-66-5]1-Bromodocosane</strong> (25.7 g) was added thereto,and the mixture was stirred at 80C for 14 hours. Water (400 mL) was added to the reaction liquid, the solution wasstirred, and then the precipitate was collected by suction filtration and washed with acetone (300 mL) and acetonitrile(300 mL) to quantitatively obtain the compound represented by E37 (23.8 g). 1H NMR (500 MHz, CDCl3) delta 7.15 (2 H, br d J = 2.1 Hz), 6.63 (1 H,t J = 6.4 Hz), 3.96 (4 H, t J = 6.3 Hz), 3.89(3 H, s, COOMe), 1.74-1.80 (4 H, m), 1.41-1.47 (4 H, m), 1.23-1.37 (72 H, br), 0.88 (6 H,t J = 7.0 Hz).

Reference： [1]Patent: US2012/296074,2012,A1
[2]Patent: US2017/320904,2017,A1 .Location in patent: Paragraph 0521-0523
[3]Tetrahedron Letters,2003,vol. 44,p. 3171 - 3174
[4]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4476 - 4479
[5]Organic Letters,2012,vol. 14,p. 5960 - 5963
[6]Patent: EP2921499,2015,A1 .Location in patent: Paragraph 0201; 0202; 0203

13
[ 6938-66-5 ]
sodium S-docosyl thiosulfate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 385 - 395

14
[ 6938-66-5 ]
[ 24463-15-8 ]
1-docosyloxymethylpyrene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 10234 - 10235

15
[ 6938-66-5 ]
[ 1198-84-1 ]
(4-docosyloxy-phenyl)-hydroxy-acetic acid [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 3441 - 3444

16
[ 6938-66-5 ]
[ 123-08-0 ]
[ 174543-48-7 ]

Reference： [1]Journal of Materials Chemistry C,2020,vol. 8,p. 3316 - 3336
[2]Organic Letters,2005,vol. 7,p. 3441 - 3444

17
[ 6938-66-5 ]
[ 86-93-1 ]
[ 886455-47-6 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 3221 - 3227

18
C₁₈₈H₁₉₄O₃₁ [ No CAS ]
[ 6938-66-5 ]
C₂₀₉H₂₃₆O₃₁ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 4808 - 4814

19
[ 6938-66-5 ]
[ 66143-74-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide;	Docosyl azide (1). Docosyl bromide (10.0 g, 25.67 mmol) in anhydrous DMF (100 ml) was treated with sodium azide (8.35 g, 128.37 mmol) at 60 C. for 2 h. Then dilution of the reaction solution with ice water (1000 ml) gave white crystal. Filtration and drying on suction funnel and vacuum gave 1 as a white crystal (9.11 g, 25.90 mmol, quant). LC-MS calcd for [M+Na]+ 621.2, found 621.2.

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 1198 - 1211
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 1645 - 1650
[3]Patent: US2012/35115,2012,A1

20
[ 6938-66-5 ]
[ 14130-06-4 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1645 - 1650
[2]Liebigs Annalen der Chemie,1994,p. 465 - 470
[3]Chemistry - A European Journal,2015,vol. 21,p. 13569 - 13576

21
[ 6938-66-5 ]
[ 505-54-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 22,p. 2816 - 2821

22
[ 6938-66-5 ]
[ 796850-49-2 ]

Yield	Reaction Conditions	Operation in experiment
49.1%		In argon atmosphere, a DMF solution (2.0 ml) of Compound 23 (85 mg, 0.188 mmol) was ice-cooled, and sodium hydride (60% in oil, 27.0 mg, 0.675 mmol) was added thereto, followed by stirring for 10 minutes under ice-cooling. Then, bromodocosane (110 mg, 0.282 mmol) was added thereto, followed by stirring for 2 hours while gradually raising the temperature of the reaction solution to room temperature. The reaction solution was ice-cooled, and methanol (1 ml) was added dropwise thereto, followed by stirring for 30 minutes. The reaction solution was diluted with ethyl acetate, and saturated sodium bicarbonate water was added thereto, followed by stirring. Then, the organic layer was washed with saturated sodium bicarbonate water and saturated brine in this order and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene : ethyl acetate = 3 : 1, 0.2% triethylamine) to obtain Compound 24-7 (70.2 mg, 49.1%). Developing solvent of Compound 24-7 (toluene : ethyl acetate = 2 : 1) Rf 0.38 C42H81NO10 MW: 760.10 1H-NMR (500 MHz, CDCl3) delta= 5.572 (br.d, 1H, H-5a), 4.909, 4.873 (2d, 2H, J = 6.6Hz, 6.8Hz, OCH2), 4.801-4.616 (m, 6H, 3OCH2), 4.190 (br.d, 1H), 4.112-4.035 (m, 3H), 3.736 (br.d, 1H), 3.406, 3.389, 3.365, 3.345 (4s, 12H, 4OCH3), 3.119 (m, 1H, NCH2), 2.887 (m, 1H, NCH2), 1.67-1.25 (m, 40H, 20CH2), 1.254 (s, 9H, CC(CH3)3), 0.880 (t, 3H, J= 7.1Hz, CH3)

Reference： [1]Patent: EP1632476,2006,A1 .Location in patent: Page/Page column 18

23
[ 6938-66-5 ]
[ 796850-61-8 ]

Yield	Reaction Conditions	Operation in experiment
29.4%		In argon atmosphere, a DMF solution (1.5 ml) of Compound 28 (80 mg, 0.177 mmol) was ice-cooled, and sodium hydride (60% in oil, 25.5 mg, 0.638 mmol) was added thereto, followed by stirring for 10 minutes under ice-cooling. Then, bromodocosane (103.5 mg, 0.266 mmol) was added thereto, followed by stirring for 2 hours while gradually raising the temperature of the reaction solution to room temperature. The reaction solution was ice-cooled, and methanol (1 ml) was added dropwise thereto, followed by stirring for 30 minutes. The reaction solution was diluted with diethyl ether, and saturated sodium bicarbonate water was added thereto, followed by stirring. Then, the organic layer was washed with saturated sodium bicarbonate water and saturated brine in this order and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (toluene : ethyl acetate = 10 : 1, 0.2% triethylamine) to obtain Compound 29-7 (39.5 mg, 29.4%). Developing solvent of Compound 29-7 (toluene : ethyl acetate = 1 : 1) Rf. 0.56 C42H81NO10 MW: 760.10

Reference： [1]Patent: EP1632476,2006,A1 .Location in patent: Page/Page column 22

24
[ 6938-66-5 ]
polyethylenimine [ No CAS ]
DOCOSYL-POLYETHYLENIMINE [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water; isopropyl alcohol;	EXAMPLE 101 PREPARATION OF 2 MOL % DOCOSYL-POLYETHYLENIMINE HCL Polyethylenimine (200 g of a 50% aqueous solution from Aldrich Chemical Co., 2.32 mol monomer equivalents) was dissolved in a mixture of ethanol (213 mL) and water (125 mL), and was heated to 70 C. in a 1-liter, round-bottomed flask equipped with an overhead mechanical stirrer, a condenser, and a thermocouple probe. <strong>[6938-66-5]1-Bromodocosane</strong> (18.1 g, 0.046 mol) was then added to the stirred solution in one portion. This mixture was stirred at 70 C. for 20 hours. The solution pH was checked periodically during this time, and was maintained at 10.0-10.2 by the addition of small quantities of 50% NaOH. After the 20 hour reaction time had elapsed, the mixture was cooled to room temperature and poured into a 20-liter bucket containing 2.4 liters of ethanol stirred with an overhead mechanical stirrer. The mixture was acidified with concentrated HCl (pH<2), resulting in the precipitation the crude product. The solvent was decanted, and the crude product was then redissolved in water (700 mL). The pH was adjusted to <2 using concentrated HCl. Isopropanol (6 liters) was then added to precipitate the product, which was collected by decantation. The solid was washed with another 2 liters of clean isopropanol and collected by decantation.

Reference： [1]Patent: US6264937,2001,B1

25
[ 6938-66-5 ]
[ 95-01-2 ]
[ 955095-30-4 ]

Yield	Reaction Conditions	Operation in experiment
99.3%	With potassium carbonate; In methanol; water; N,N-dimethyl-formamide;	(1) Synthesis of 2,4-bis(docosyloxy)benzaldehyde Under an argon atmosphere, 2,4-dihydroxybenzaldehyde (3.00 g, 21.7 mmol), potassium carbonate (30.0 g, 217 mmol) and <strong>[6938-66-5]1-bromodocosane</strong> (17.3 g, 44.5 mmol) were added to dehydrating N,N-dimethylformamide (150 mL), and the mixture was stirred at 70 C. overnight. After completion of the reaction, the reaction mixture was poured into purified water (1 L), the mixture was stirred for 1 hr, and the precipitated solid was collected by filtration. The obtained solid was slurry-washed in methanol and filtered, and the obtained solid was dried under reduced pressure to give the title compound (16.3 g, 99.3%) as a white solid.
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 8h;	Example 1: Synthesis of an Amine Having a Hydrophobic Carrier Group; One gram of 2,4-dihydroxybenzaldehyde, 8.4 g of <strong>[6938-66-5]1-bromodocosane</strong>, and 6 g of potassium carbonate were dissolved in 20 ml of N,N-dimethylformamide, and reacted for 8 hours under a nitrogen gas flow at 80C. After confirming the completion of the reaction by thin layer chromatography, 20 ml of toluene and 10 ml of water were added to the reaction liquid and stirred for 5 min at 80C. The toluene layer was separated with a separatory funnel and after removal by distillation of the solvent, 50 ml of methanol were added and crystals were precipitated. This solution was subjected to suction filtration with a separatory funnel and 6.97 g of crude crystals were obtained. After dissolving the crude crystals in 200 ml of hexane at 70C and recrystallizing at room temperature, suction filtration was again carried out with a separatory funnel, and 4.7 g of the desired compound 3 were obtained. The yield was 85%. Compound 3;2,4-bis(docosyloxy)benzaldehyde.

Reference： [1]Patent: US2012/296074,2012,A1
[2]Patent: EP2003104,2008,A2 .Location in patent: Page/Page column 17

26
[ 6938-66-5 ]
[ 1092960-32-1 ]
C₁₅₈H₂₂₄N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With sodium hydride; In N,N-dimethyl acetamide; at 40 - 80℃; for 8h;	Example A7; In a 100-mL four-necked flask was placed 0.25 g (10 mmol) of sodium hydride, and 20 g of N,N-dimethylacetamide (DMAc) was added thereto at 25C in a nitrogen atmosphere. To this was added 3.2 g (10 mmol) of <strong>[6938-66-5]1-bromodocosane</strong> of Formula (T). Additionally, a solution of 2 g (2 mmol) of the ethynyl-containing adamantane derivative of Formula (Q) in 10 g of DMAc was prepared and added dropwise through a dropping funnel to the mixture in the four-necked flask at 40C. After the completion of dropwise addition, the mixture was stirred at 80C for 8 hours. After the completion of reaction, the reaction mixture was cooled to 25C and combined with 80 g of methanol. Next, 160 g of hexane was added followed by stirring, and the mixture was separated, from which a hexane layer was obtained. The hexane layer was combined with 100 g of pure water, stirred, and separated, from which a hexane layer was obtained again. The hexane layer was concentrated and purified by silica gel column chromatography with hexane as a developing solvent. The resulting hexane solution (eluate) was left stand for 24 hours to precipitate solids. The solids were separated from a liquid by decantation, and dried in a vacuum drier to give a product. The 1H-NMR spectrum of the product was measured (see FIG. 6) to find that an N-substituted ethynylbenzimidazole-containing bridged alicyclic compound of Formula (U) was formed. The N-substituted ethynylbenzimidazole-containing bridged alicyclic compound was obtained in an amount of 1.0 g and a yield of 22%.[NMR Spectral Data] 1H-NMR (CDCl3) delta (ppm): 0.8 (12H), 1.2 (152H), 1.8 (8H), 2.3 (12H), 3.0-3.1 (4H), 4.2 (8H), 7.3-8.0 (28H)

Reference： [1]Patent: EP2003123,2008,A2 .Location in patent: Page/Page column 57-58

27
[ 6938-66-5 ]
[ 99-24-1 ]
[ 911494-81-0 ]

Yield	Reaction Conditions	Operation in experiment
86%		To methyl gallate (5.5 g) and potassium carbonate (62.2 g), 1,3-dimethyl-2-imidazolidinone (140 mL) wasadded, then the mixture was stirred at 80C for 1 hour and then was cooled to 70C. <strong>[6938-66-5]1-Bromodocosane</strong> (38.6 g) wasadded thereto, and the mixture was stirred at 70C for 14 hours. Water (300 mL) was added to the reaction liquid, thesolution was stirred, then the precipitate was collected by suction filtration and washed with water (300 mL), acetonitrile(200 mL), acetone (500 mL), and dichloromethane (200 mL) to obtain the compound represented by E36 (28.6 g, percentyield: 86%). 1H NMR (500 MHz, CDCl3) delta 7.25 (2 H, s), 3.99-4.03 (6 H, m), 3.89 (3 H, s, COOMe), 1.71-1.84 (6 H, m), 1.47(6 H, m), 1.22-1.38 (108 H, br), 0.88 (9 H,t J = 9.0 Hz).

Reference： [1]Patent: EP2921499,2015,A1 .Location in patent: Paragraph 0188; 0189; 0190
[2]Tetrahedron Letters,2010,vol. 51,p. 4579 - 4583

28
[ 6938-66-5 ]
[ 6949-73-1 ]
[ 1245574-80-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	Example 1 1-1: Synthesis of 2-docosyloxy-9-fluorenone 2-Hydroxy-9-fluorenone (196 mg, 2.04 mmol) was dissolved in DMF (8 ml), potassium carbonate (423 mg, 3.06 mmol) and docosyl bromide (96%, 785 mg, 1.93 mmol) were added. The mixture was heated to 80C and stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, and 1N hydrochloric acid (4 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (23 ml), and washed once with 1N hydrochloric acid (7.5 ml) and 4 times with pure water (7.5 ml). The solvent of the organic layer was evaporated, and the residue was precipitated with methanol (10 ml) to give 2-docosyloxy-9-fluorenone (934 mg, 1.85 mmol, 96%). 1H-NMR (400MHz) 0.88 (3H, t, J=7.0, C21H42-Me) 1.20-1.40 (36H, br, alkyl-H) 1.45 (2H, br, -O-C2H4-CH2-C19H39) 1.79 (2H, m, -O-CH2-CH2-) 4.00 (2H, t, J=6.6, -O-CH2-) 6.97 (1H, fluorenone C3-H) 7.19 (2H, fluorenone C1,7-H) 7.38-7.43 (3H, fluorenone C4,5,6-H) 7.59 (1H, fluorenone C8-H) MS 505 [M+H]
	With hydrogenchloride; potassium carbonate; In water; N,N-dimethyl-formamide;	Example 1 1-1: Synthesis of 2-docosyloxy-9-fluorenone 2-Hydroxy-9-fluorenone (196 mg, 2.04 mmol) was dissolved in DMF (8 ml), potassium carbonate (423 mg, 3.06 mmol), and docosyl bromide (96%, 785 mg, 1.93 mmol) were added. The mixture was heated to 80 C. and stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, and 1N hydrochloric acid (4 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (23 ml), and washed once with 1N hydrochloric acid (7.5 ml) and 4 times with pure water (7.5 ml). The solvent of the organic layer was evaporated, and the residue was precipitated with methanol (10 ml) to give 2-docosyloxy-9-fluorenone (934 mg, 1.85 mmol, 96%). 1H-NMR(400 MHz) 0.88 (3H, t, J=7.0, C21H42-) 1.20-1.40 (36H, br, alkyl-H) 1.45 (2H, br, -O-C2H4-C-C19H39) 1.79 (2H, m, -O-CH2-C-) 4.00 (2H, t, J=6.6, -O-C-) 6.97 (1H, fluorenone C3-H) 7.19 (2H, fluorenone C1,7-H) 7.38-7.43 (3H, fluorenone C4,5,6-H) 7.59 (1H, fluorenone C8-H)

Reference： [1]Patent: EP2415744,2012,A1 .Location in patent: Page/Page column 30
[2]Patent: US2010/240867,2010,A1

29
[ 6938-66-5 ]
[ 42523-29-5 ]
[ 1245574-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium carbonate; In methanol; water; N,N-dimethyl-formamide;	Example 2 2-1: Synthesis of 2,7-didocosyloxy-9-fluorenone <strong>[42523-29-5]2,7-Dihydroxy-9-fluorenone</strong> (1 g, 4.71 mmol) was dissolved in DMF (40 ml), and potassium carbonate (1.95 g, 14.1 mmol) and docosyl bromide (96percent, 4.02 g, 9.91 mmol) were added. The mixture was stirred overnight at 80° C., docosyl bromide (0.40 g, 0.99 mmol) was further added and the mixture was stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, 1N hydrochloric acid (120 ml) was added thereto in a water bath to allow precipitation. The crystals were collected by filtration and slurry washed once with 1N hydrochloric acid (40 ml), once with pure water (40 ml) and once with methanol (40 ml) to give 2,7-didocosyloxy-9-fluorenone (4.20 g, docosyl bromide mixture). 1H-NMR(300 MHz) 0.88 (6H, t, J=6.6, C21H42-) 1.15-1.60 (80H, br, alkyl-H) 1.78 (4H, m, -O-CH2-C-) 3.98 (4H, t, J=6.6, -O-CH2-) 6.92 (2H, fluorenone C3,6-H) 7.14 (2H, d, J=2.1, fluorenone C1,8-H) 7.26 (2H, d, J=7.8, fluorenone C4,5-H) 7.59 (1H, fluorenone C8-H)
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	Example 22-1:Synthesis of 2,7-didocosyloxy-9-fluorenone<strong>[42523-29-5]2,7-Dihydroxy-9-fluorenone</strong> (1 g, 4.71 mmol) was dissolved in DMF (40 ml), and potassium carbonate (1.95 g, 14.1 mmol) and docosyl bromide (96percent, 4.02 g, 9.91 mmol) were added.The mixture was stirred overnight at 80°C, docosyl bromide (0.40 g, 0.99 mmol) was further added and the mixture was stirred overnight.After completion of the reaction, the reaction mixture was cooled to room temperature, 1N hydrochloric acid (120 ml) was added thereto in a water bath to allow precipitation.The crystals were collected by filtration and slurry washed once with 1N hydrochloric acid (40 ml), once with pure water (40 ml) and once with methanol (40 ml) to give 2,7-didocosyloxy-9-fluorenone (4.20 g, docosyl bromide mixture).1H-NMR(300MHz)0.88 (6H, t, J=6.6, C21H42-Me) 1.15-1.60 (80H, br, alkyl-H) 1.78 (4H, m, -O-CH2-CH2-) 3.98 (4H, t, J=6.6, -O-CH2-) 6.92 (2H, fluorenone C3,6-H) 7.14 (2H, d, J=2.1, fluorenone C1,8-H) 7.26 (2H, d, J=7.8, fluorenone C4,5-H) 7.59 (1H, fluorenone C8-H)MS829 [M+H]

Reference： [1]Patent: US2010/240867,2010,A1
[2]Patent: EP2415744,2012,A1 .Location in patent: Page/Page column 31
[3]Tetrahedron Letters,2012,vol. 53,p. 1936 - 1939

30
[ 673-22-3 ]
[ 6938-66-5 ]
[ 1313025-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium borohydrid; potassium carbonate; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;	Example 5 Synthesis of 2-docosyloxy-4-methoxybenzyl alcohol 2-Hydroxy-4-methoxybenzaldehyde (5 g, 32.9 mmol), <strong>[6938-66-5]1-bromodocosane</strong> (16.6 g, 42.7 mmol) and potassium carbonate (14.8 g, 107 mmol) were mixed with DMF (150 ml), and the mixture was stirred at 100 C. for 7 hr. Chloroform (400 ml) and 1N hydrochloric acid (300 ml) were added to the reaction mixture, and the mixture was washed. The organic layer was washed successively with 1N hydrochloric acid and saturated brine. The organic layer was concentrated and slurry-washed with methanol. The precipitate was collected by filtration and dried under reduced pressure. The obtained dried crystals were dissolved in THF (150 ml), sodium borohydride (3.7 g) was added, and the mixture was stirred at 40 C. for 3 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was concentrated. The mixture was extracted with chloroform, and washed successively with aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was concentrated. The obtained residue was washed with acetonitrile, and the precipitate was collected by filtration and dried under reduced pressure to give 2-docosyloxy-4-methoxybenzyl alcohol (9.8 g). 1H-NMR (300 MHz, CDCl3): delta0.88(3H, t, J=6.5 Hz), 1.21-1.55(38H, m), 1.76-1.85(2H, m), 3.80(3H, s), 3.98(2H, t, J=6.3 Hz), 4.62(2H, s), 6.42-6.42(2H, m), 7.15(1H, d, J=7.8 Hz)

Reference： [1]Patent: US2011/160433,2011,A1

31
[ 6938-66-5 ]
[ 2150-47-2 ]
methyl 2,4-di(docosyloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 16h;Inert atmosphere;	Under an argon atmosphere, potassium carbonate (29.9 g, 217 mmol), methyl 2,4-dihydroxybenzoate (3.65 g, 21.7 mmol), <strong>[6938-66-5]1-bromodocosane</strong> (17.33 g, 44.5 mmol) were dissolved in N,N-dimethylformamide (150 mL), and the mixture was stirred at 70 C. for 16 hr. Completion of the reaction was confirmed by thin layer chromatography, and the reaction solution was poured into water (1.00 L) to allow for precipitation to give a solid. The obtained solid was dissolved in dichloromethane (500 mL), and the solid was precipitated with methanol (400 mL), collected by filtration, and dried to give the object compound (16.7 g, yield 98%). 1H-NMR (400 MHz, CDCl3): delta=0.88 (t, 6H, J=6.6 Hz, -CH3), 1.13-1.56 (m, 76H, -OCH2CH2 (CH2)19CH3) 1.81 (m, 4H, -OCH2CH2(CH2)19CH3), 3.89 (s, 3H, C(O)O-CH3), 4.02 (dd, 4H, J=6.6, 14.8 Hz, -OCH2CH2(CH2)19CH3) 6.63 (s, 1H, Ar-H) 7.15 (s, 2H, Ar-H)

Reference： [1]Patent: US2017/320904,2017,A1 .Location in patent: Paragraph 0553-0555
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4476 - 4479
[3]Organic Letters,2012,vol. 14,p. 5960 - 5963
[4]Tetrahedron,2013,vol. 69,p. 2555 - 2559

32
[ 2439-35-2 ]
[ 6938-66-5 ]
[ 1345828-62-7 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 11697 - 11699

33
[ 6938-66-5 ]
[ 611-99-4 ]
[ 1246541-58-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 6.5h;	4-1: synthesis of 4,4'-didocosoxy-benzophenone To 4,4'-dihydroxy-benzophenone (8.2 g, 38.3 mmol) and <strong>[6938-66-5]1-bromodocosane</strong> (31.3 g, 80.4 mmol) were added DMF (300 mL) and potassium carbonate (15.9 g, 115 mmol) and the mixture was stirred at 80C for 6.5 hr. After confirmation of disappearance of monoalkylated form, the reaction mixture was ice-cooled and 1N hydrochloric acid (300 mL) and water (150 mL) were slowly added with sufficient stirring. The slurry was filtered, and the obtained crystals were washed with water and methanol to give 4,4'-didocosoxy-benzophenone (28.3 g, 34.1 mmol, 89%). 1H-NMR (CDCl3/300MHz) delta= 0.88 (6H, t, J=6.6 Hz, OC22H45 C22-H) 1.1-1.6 (76H, br, OC22H45 C3-21-H) 1.81 (4H, m, OC22H45 C2-H) 2.04 (1H, s, -OH) 4.03 (4H, t, J=6.5 Hz, OC22H45 C1-H) 6.94 (4H, d, J=8.8 Hz, Ph C3,3',5,5'-H) 7.77 (4H, d, J=8.7 Hz, Ph C2,2',6,6'-H)
	With hydrogenchloride; potassium carbonate; In water; N,N-dimethyl-formamide;	(1) Synthesis of 4,4'-didocosyloxy-benzophenone To 4,4'-dihydroxy-benzophenone (8.2 g, 38.3 mmol) and <strong>[6938-66-5]1-bromodocosane</strong> (31.3 g, 80.4 mmol) were added DMF (300 mL) and potassium carbonate (15.9 g, 115 mmol), and the mixture was stirred at 80 C. for 6.5 hr. After confirmation of the disappearance of the monoalkylated compound, the reaction mixture was ice-cooled, and 1N hydrochloric acid (300 mL) and water (150 mL) were slowly added to the thoroughly-stirred mixture. The slurry was filtered, and the obtained crystals were washed with water and methanol to give the title compound (28.3 g, 34.1 mmol, 89%). 1H-NMR (CDCl3/300 MHz) delta=0.88 (6H, t, J=6.6 Hz, OC22H45 C22-H), 1.1-1.6 (76H, br, OC22H45C3-21-H), 1.81 (4H, m, OC22H45C2-H), 2.04 (1H, s, -OH), 4.03 (4H, t, J=6.5 Hz, OC22H45C1-H), 6.94 (4H, d, J=8.8 Hz, Ph C3,3',5,5'-H), 7.77 (4H, d, J=8.7 Hz, Ph C2,2',6,6'-H)

Reference： [1]Organic Letters,2012,vol. 14,p. 4514 - 4517
[2]Patent: EP2415745,2012,A1 .Location in patent: Page/Page column 27
[3]Patent: US2012/296074,2012,A1

34
[ 6938-66-5 ]
[ 1883-85-8 ]
(+/-)-trans-2-(docosyloxymethyl)cyclopentanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%		General procedure: To a stirred solution of (+/-)-(trans-2-hydroxymethyl)cyclopentanol (trans-9, 1 eq.) in DMF (5 mL) was added sodium hydride (60% dispersion in mineral oil, 1.5 eq.) at 0 C. The mixture was stirred for 30 min and then treated with several bromoalkanes (1.2 eq) at the same temperature. After stirring at 0 C (for compounds 10a and 10b) or rt (for compounds 10c-e) for 4 h, the reaction mixture was poured into ice water and extracted twice with diethyl ether. The combined organic layer was dried over anhydrous MgSO4, concentrated, and purified by column chromatography (ethyl acetate/n-hexane = 1:4) on silica gel to afford 10a-e.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 485 - 492

35
[ 6938-66-5 ]
(+/-)-cis-2-(benzyloxymethyl)cyclopentanol [ No CAS ]
((((+/-)-cis-2-(docosyloxy)cyclopentyl)methoxy)methyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		General procedure: To a stirred solution of 11 and 14 (1.2 eq.) in DMF (10 mL) was added NaH (60% dispersion in mineral oil, 1.5 eq.) at 0 C and stirred for 30 min. To the mixture was added bromoalkane (1.2 eq.) and stirred at rt overnight. The reaction mixture was then poured into ice water and extracted three times with diethyl ether. The combined organic layer was dried over anhydrous MgSO4, concentrated, and purified by column chromatography (ethyl acetate/n-hexane = 1:9) on silica gel to afford 12a-e and 15a-e.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 485 - 492

36
[ 6938-66-5 ]
(+/-)-trans-2-(benzyloxymethyl)cyclopentanol [ No CAS ]
((((+/-)-trans-2-(docosyloxy)cyclopentyl)methoxy)methyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%		General procedure: To a stirred solution of 11 and 14 (1.2 eq.) in DMF (10 mL) was added NaH (60% dispersion in mineral oil, 1.5 eq.) at 0 C and stirred for 30 min. To the mixture was added bromoalkane (1.2 eq.) and stirred at rt overnight. The reaction mixture was then poured into ice water and extracted three times with diethyl ether. The combined organic layer was dried over anhydrous MgSO4, concentrated, and purified by column chromatography (ethyl acetate/n-hexane = 1:9) on silica gel to afford 12a-e and 15a-e.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 485 - 492

37
[ 6938-66-5 ]
[ 1360771-76-1 ]

Reference： [1]Dalton Transactions,2012,vol. 41,p. 4306 - 4309

38
[ 111-51-3 ]
[ 6938-66-5 ]
[ 1400321-33-6 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; acetonitrile; at 20 - 70℃;	C22-4-4Br2: The surfactant (C22H45-N+(CH3)2-C4H8-N+(CH3)2-C4H9)Br2 was synthesized following a published procedure [9]. First, 4.1 g (0.01 mol) <strong>[6938-66-5]1-bromodocosane</strong> (Aldrich, 96%) was dissolved in 20 ml toluene and added dropwise into the 20 ml solution of 10.3 g (0.07 mol) N,N,N?,N?-tetramethyl-1,4-butanediamine (Aldrich, 98%) in acetonitrile. The resulting solution was stirred for 3 h at room temperature and then mixed at 70 C under reflux overnight. After cooling to room temperature, the solution was kept in a refrigerator at 4 C for 1 h, filtered and washed with diethyl ether. The resulting solid was dried in a vacuum oven at room temperature. The product was (C22H45-N+(CH3)2-C4H8-N(CH3)2)Br. Second, 3.7 g (0.007 mol) (C22H45-N+(CH3)2-C4H8-N(CH3)2)Br and 1.96 g (0.014 mol) 1-bromobutane (Aldrich, 98%) were dissolved in 110 ml of acetonitrile and then stirred in a reflux condenser at 70 C overnight. Next, the solid product was quenched in refrigerator at 4 C for 1 h, filtered, washed with diethyl ether and dried in a vacuum oven at room temperature. The resulting product was (C22H45-N+(CH3)2-C4H8-N+(CH3)2-C4H9)Br2 (denoted as C22-4-4Br2).

Reference： [1]Chemical Communications,2012,vol. 48,p. 9492 - 9494
[2]Catalysis Today,2014,vol. 235,p. 160 - 168

39
[ 111-51-3 ]
[ 6938-66-5 ]
C₃₄H₇₄N₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene; acetonitrile / 20 - 70 °C 2: acetonitrile / 70 °C

Reference： [1]Wu, Leilei; Degirmenci, Volkan; Magusin, Pieter C. M. M.; Szyja, Bartlomiej M.; Hensen, Emiel J. M. [Chemical Communications, 2012, vol. 48, # 76, p. 9492 - 9494]

40
[ 111-18-2 ]
[ 6938-66-5 ]
[ 1214738-94-9 ]

Yield	Reaction Conditions	Operation in experiment
81.09%	In N,N-dimethyl-formamide; acetone; at 60℃; for 12h;Reflux;	A three-necked flask with a thermometer was added 45mL N,N',N',N-tetramethylhexylDiamine,alphamL acetone and betamL dimethylformamide (alpha and beta specific values shown in Table 1), slowly stirred, warmed to 60 ,With a dropping funnel was slowly added 36mL 1-bromo docosane,After the addition is completed,Reflux reaction 12h,At this point the reaction was viscous, cooled to room temperature, filtered, washed with acetone, 50 drying. The intermediate product C22H45Br-N (CH3)2-(CH2)6-N(CH3)2 was obtained. The yields of intermediate products obtained with different ratios of acetone and dimethylformamide are shown in Table 1.

Reference： [1]Patent: CN106674017,2017,A .Location in patent: Paragraph 0035; 0044; 0045; 0047; 0049; 0054; 0074; 0076
[2]Chemical Communications,2012,vol. 48,p. 9492 - 9494
[3]RSC Advances,2014,vol. 4,p. 13831 - 13838
[4]Chemistry of Materials,2014,vol. 26,p. 1345 - 1355
[5]RSC Advances,2015,vol. 5,p. 63765 - 63776

41
[ 673-22-3 ]
[ 6938-66-5 ]
C₃₀H₅₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 7h;	2-Hydroxy-4-methoxybenzaldehyde (5 g, 32.9 mmol), <strong>[6938-66-5]1-bromodocosane</strong> (16.6 g, 42.7 mmol) and potassium carbonate (14.8 g, 107 mmol) were mixed with DMF (150 ml), and the mixture was stirred at 100C for 7 hr. Chloroform (400 ml) and 1N hydrochloric acid (300 ml) were added to the reaction mixture, and the mixture was washed. The organic layer was washed successively with 1N hydrochloric acid and saturated brine. The organic layer was concentrated and slurry-washed with methanol. The precipitate was collected by filtration and dried under reduced pressure. The obtained dried crystals were dissolved in THF (150 ml), sodium borohydride (3.7 g) was added, and the mixture was stirred at 40C for 3 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was concentrated. The mixture was extracted with chloroform, and washed successively with aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was concentrated. The obtained residue was washed with acetonitrile, and the precipitate was collected by filtration and dried under reduced pressure to give 2-docosyloxy-4-methoxybenzyl alcohol (9.8 g). 1H-NMR(300MHz, CDCl3): delta0.88(3H, t, J=6.5Hz), 1.21-1.55(38H, m), 1.76-1.85(2H, m), 3.80(3H, s), 3.98(2H, t, J=6.3Hz), 4.62(2H, s), 6.42-6.42(2H, m), 7.15(1H, d, J=7.8Hz)

Reference： [1]Patent: EP2518041,2012,A1 .Location in patent: Paragraph 0212; 0213

42
[ 6938-66-5 ]
[ 611-10-9 ]
[ 1428444-41-0 ]

Yield	Reaction Conditions	Operation in experiment
95%		General procedure: To a suspension of K2CO3 (2.5 mmol) and KI (0.35 mmol) in anhydrous acetone was added slowly a solution of ethyl-2-oxocyclopentanecarboxylate (1 mmol) in anhydrous acetone. After 10 min, a solution of bromoalkane (1.1 mmol) in acetone (10 ml) was added and the mixture was stirred at reflux. After 20 h, the reaction mixture was cooled to rt, diluted with ether (50 ml) and filtered over Celite pad. The filtrate was concentrated at reduce pressure, dilute with ether and washed with water and brine. The organic layer was dried over MgSO4 and evaporated under reduce pressure. The residue was purified by column chromatography (EtOAc/n-hexane) to give compound 7a-e in 94-99% yield.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2018 - 2024

43
[ 6938-66-5 ]
[ 605-32-3 ]
[ 1430074-47-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2013,vol. 86,p. 354 - 362

44
[ 616-47-7 ]
[ 6938-66-5 ]
[ 943834-80-8 ]

Yield	Reaction Conditions	Operation in experiment
81.4%	In acetonitrile; at 85℃; for 24h;	Typically, 2.0 g (0.025 mol) of 1-methylimidazole and 10.7 g (0.026mol) of <strong>[6938-66-5]1-bromodocosane</strong> were dissolved in 20 mL of acetonitrile. The mixture was refluxed at 85C for 24 h, and subsequently cooled down to room temperature. The resulting sample (cake-like) was filtered and washed with ethyl ether three times. The final product: 1-docosanyl-3-methylimidazolium bromide was obtained as a white powder after being dried in a vacuum oven. The yield based on this procedure was 81.4%. The spectra of 1H NMR (CDCl3 as the solvent, delta, ppm) were: 10.713 (N-CH-N, s, 1H), 7.274 (N-CH-CH, s, 1H), 7.218 (N-CH-CH, s, 1H), 4.310 (N-CH2, t, 2H), 4.130 (N-CH3, s, 3H), 1.918 (N-CH2-CH2, m, 2H), 1.248 (N-CH2-CH2-(CH2)19, m, 38H), 0.874 (CH3, t, 3H).

Reference： [1]Polymer,2014,vol. 55,p. 160 - 165
[2]Chemical Physics Letters,2015,vol. 628,p. 9 - 15

45
[ 2867-47-2 ]
[ 6938-66-5 ]
[ 406160-42-7 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 70℃; for 24h;	In a 20 mL scintillation vial, 10 mmol of DMAEMA and 10 mmol of <strong>[6938-66-5]1-bromodocosane</strong> (BDO, TCI America, Portland OR) were added. To this mixture, 3 g of ethanol was added as a solvent. A magnetic stir bar was added, and the vial was capped and stirred at 70 C for 24 h. After the reaction was complete, the ethanol solvent was removed via evaporation at room temperature over several days.

Reference： [1]Patent: WO2014/62347,2014,A1 .Location in patent: Paragraph 0060

46
[ 6938-66-5 ]
[ 1609953-44-7 ]
[ 1609953-47-0 ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium carbonate; at 100℃; for 22h;	A solution of 6 (245 mg, 0.44 mmol.), bromodocosane (172 mg, 1 equiv.) and Na2CO3(94 mg, 2 equiv.) in propionitrile (25 mL) was stirred, at 100 C, for 22 h. Propionitrile was evaporated under reduced pressure. Purification by column chromatography (acetone/NEt395 :5) afforded the pure 7 compound (120 mg, 33%) as a yellow oil. 1H NMR (400 MHz,CDCl3): 0.88 (t, 3J = 6.8 Hz, 3H, CH3), 1.25 (bs, 38H, CH2(3-21)), 1.35-1.50 (m, 2H, CH2(2)),2.45 (bt, 2H, 3J = 6.8 Hz, NCH2(1)), 2.65-2.83 (m, 4H, NCOCH2), 2.65-2.83 (m, 4H, NCH2),3.50-3.85 (m, 36H, 28 OCH2, 8 NCH2) ppm. 13C NMR (100.6 MHz, CDCl3): delta = 14.1(C(22)), 22.7 (C(21)), 27.4 (C(3)), 28.4 (C(2)), [29.3, 29.6, 29.7, 30.9, 31.9] (16C, C(4-19)),[48.8, 49.4, 49.7, 50.3] ( 4C, CH2NCO), [53.9, 54.4] (2C, NCH2), 56.8 (NC(1)), [69.0, 69.4,69.6, 70.1, 70.3, 70.5, 70.7, 71.5] (14C, OCH2), 172.4, 172.5 (2C, NCO) ppm. IR (KBr): nu =720, 1119, 1293, 1355, 1467, 1642 cm-1. HRMS (ESI-Q-Tof) : calcd for C46H89N3NaO9[M+Na].+ 850.6491 ; found 850.6494.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 1888 - 1892

47
[ 6938-66-5 ]
[ 608-33-3 ]
2,6-dibromo-1-n-docosyloxybenzene [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 9903 - 9906

48
[ 6938-66-5 ]
[ 10111-08-7 ]
1-docosyl-1H-imidazole-2-carbaldehyde [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 8442 - 8454

49
[ 136918-14-4 ]
[ 6938-66-5 ]
[ 107513-47-3 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 13569 - 13576

50
[ 6938-66-5 ]
[ 403-01-0 ]
C₃₀H₅₁FO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		To <strong>[403-01-0]methyl 3-fluoro-4-hydroxybenzoate</strong> (850 mg) and potassium carbonate (3.5 g), 1,3-dimethyl-2-imidazolidinone(10 mL) was added, and the mixture was stirred at 70°C for 15 minutes. 1-Bromodocosane (2.1 g) was addedthereto, and the mixture was stirred at 70°C for 13 hours. Water (200 mL) was added to the reaction liquid, the solutionwas stirred, then the precipitate was collected by suction filtration and washed with acetonitrile (100 mL) to obtain thecompound represented by E39 (2.2 g, percent yield: 93percent). 1H NMR (500 MHz, CDCl3) delta 7.79 (1 H,br d J = 8.6 Hz), 7.73 (1 H, dd J = 11.7, 2.0 Hz), 6.96 (1 H, t J = 8.3Hz), 4.08 (2 H, t J = 6.6 Hz), 3.89 (3 H, s), 1.84 (2 H, m), 1.47 (2 H, m), 1.19-1.37 (36 H, br), 0.88 (3 H,t J = 7.0 Hz).

Reference： [1]Patent: EP2921499,2015,A1 .Location in patent: Paragraph 0221; 0222; 0223

51
[ 3943-74-6 ]
[ 6938-66-5 ]
C₃₁H₅₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		To methyl vanillate (4.6 g) and potassium carbonate (17.3 g), 1,3-dimethyl-2-imidazolidinone (80 mL) wasadded, then the mixture was stirred at 80C for 30 minutes and then was cooled to 70C. <strong>[6938-66-5]1-Bromodocosane</strong> (10.7 g)was added thereto, and the mixture was stirred at 70C for 15 hours. Water (300 mL) was added to the reaction liquid,the solution was stirred, then the precipitate was collected by suction filtration and washed with water and acetonitrileto obtain the compound represented by E38 (12.1 g, percent yield: 99%). 1H NMR (500 MHz, CDCl3) delta 7.65 (1 H, dd J = 8.5, 1.9 Hz), 7.54 (1 H, d J = 1.9 Hz), 6.87 (1 H, d J = 8.5 Hz),4.06 (2 H, t J = 6.9 Hz), 3.89 (3 H, s), 3.9 (3 H, s), 1.86 (2 H, m), 1.46 (2 H, m), 1.21-1.39 (36 H, br), 0.88 (3 H,t J = 7.0 Hz).

Reference： [1]Patent: EP2921499,2015,A1 .Location in patent: Paragraph 0211; 0212; 0213

52
[ 6938-66-5 ]
C₁₄H₂₄O₃ [ No CAS ]
C₃₆H₇₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		To a mixture of magnesium 181 mg (7.44 mmol) and crashed glass in THF (0.750 mL)catalytic amount of I2 was added. After stirring for 30 min at 45 C until the yellowcolor disappeared, a solution of <strong>[6938-66-5]1-bromodocosane</strong> (894 mg, 2.30 mmol) in THF (1.55mL) was added via cannula. Then, CuI (44.0 mg, 0.231 mmol) was added to theresulting mixture at room temperature. After stirring for 1 h, a solution of compound 13(54.9 mg, 0.229 mmol) in THF (0.550 mL) was added via cannula and the resultingmixture was stirred for 30 min. After reaction was completed, sat. NH4Cl aq. (0.500mL) was added and the resulting mixture was filtered. The organic layer was separatedand the aqueous layer was extracted with CHCl3 (15.0 mL×3). The combined organiclayer was concentrated in vacuo. The residue was purified by column chromatographyon silica gel (n-hexane : EtOAc = 7 : 1) to give the compound 14 as a white solid (81.4mg, 0.148 mmol, 65 %).

Reference： [1]Chemistry Letters,2016,vol. 45,p. 550 - 551

53
[ 111-18-2 ]
[ 6938-66-5 ]
C₃₂H₆₉N₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 49.84℃; for 48h;	The C22-6-6 surfactant of formula C22H45-N+(CH3)2-C6H12-N+(CH3)2-C6H13 was prepared as described by Minkee et al. and confirmed by 1H NMR (Bruker Avance instrument 300 MHz) in CDCl3. The first nucleophilic substitution was typically performed using 16 g of <strong>[6938-66-5]1-bromodocosane</strong> (TCI, 98%) and 70 g of N,N,N,N-tetramethyl-1,6-diaminohexane (TCI, 98%), which were dissolved in acetonitrile and heated at 323 K under stirring for 48 h. The total substitution was confirmed by 1H NMR, with the disappearance of the signal near 3.5 ppm. The solvent was evaporated and the product, denoted C22-6-0, was washed with ether and dried in a vacuum oven for 12 h.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2016,vol. 422,p. 115 - 121

54
[ 6938-66-5 ]
4,4'-((1E,1'E)-(2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-3,9-diyl) bis(diazene-2,1-diyl)) bis (2,6-dimethylphenol) [ No CAS ]
3,9-bis((E)-(4-(docosyloxy)-3,5-dimethylphenyl)diazenyl)-2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate; potassium iodide; In acetone; for 12h;Darkness; Reflux;	General procedure: Appropriate amounts of 1, KI and K2CO3 were mixed in 10 ml of acetone, then an alkyl or aryl halide was injected into the mixture and refluxed in darkness. The reaction was monitored by TLC until showed a single spot at the conclusion (Indicated in Scheme 2). Afterwards, 50 ml of water was added and the crude was extracted with EtOAc(3×30ml). The collected organic layers were combined and dried over MgSO4 and filtered off. After removing thesolvent, the residue was chromatographed to obtain the orange sticky solids 2-16 (Scheme 2).

Reference： [1]Synthesis,2017,vol. 49,p. 1214 - 1222

55
[ 6938-66-5 ]
[ 107-11-9 ]
N,N-didocosyl allylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With sodium hydroxide; In tetrahydrofuran; at 120℃; for 24h;Sealed tube;	A methylene chloride (3.8 mL) solution of didocosylamine allylamine (516 mg, 0.766 mmol), tetrakispalladium (44.2 mg, 0.0383 mmol) and N,N-dimethylbarbituric acid (359 mg, 2.30 mmol) was stirred at room temperature for 2 hours, then water was added to the reaction mixture, and the mixture was extracted with chloroform twice. The extracts were combined, washed with a saturated aqueous sodium bicarbonate solution and brine, dried with magnesium sulfate, and then concentrated under reduced pressure. Then, the residue was purified with silica gel column chromatography (eluent: hexane/diethyl ether=50/50) to yield didocosylamine (360 mg, 0.567 mmol, yield: 74%). 1H-NMR: 2.59 (t, 4H, J=7.3 Hz), 1.64-1.54 (m, 4H), 1.50-1.44 (m, 4H), 1.32-1.20 (m, 72H).

Reference： [1]Patent: US2017/66748,2017,A1 .Location in patent: Paragraph 0085; 0086-0087

56
[ 6938-66-5 ]
[ 3883-95-2 ]
3-docosylsalicylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97.1%		To a 500 mL glass vessel equipped with a stirrer, a thermometer, a heating jacket and a nitrogen gas pipe were added diethyl ether 25. 0. g, 1-bromododecane 97. 38 g, metallic lithium 3. 47 g, reacted at -10 C for 2 h , Followed by addition of cuprous iodide 23. 81g, reaction at 0 C lh. The mixture was washed with water and the layers were removed and added with <strong>[3883-95-2]3-bromosalicylic acid</strong>, 27 g, and kept at 60 C for 12 h. After the completion of the reaction, the mixture was washed with water and the water and ether were distilled off to give a reddish-brown liquid as an alkyl salicylic acid. Nuclear magnetic analysis The product contains 3-docosyl salicylic acid 97. 12%.

Reference： [1]Patent: CN106518647,2017,A .Location in patent: Paragraph 0033; 0034

57
[ 6938-66-5 ]
[ 89-55-4 ]
5-docosylsalicylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97.9%		In a 500 mL glass vessel equipped with a stirrer, a thermometer, a heating jacket and a nitrogen gas pipe was added diethyl ether 25. 0. g, 1-bromododecane 97. 38 g, metallic lithium 3. 47 g, reacted at -10 C for 2 h, followed by addition of cuprous iodide 23. 81 g l l C reaction lh. The mixture was washed with water and the layers were removed by addition of 5-bromosalicylic acid, 27 g of water Keep at 60 C 12h. After the completion of the reaction, the mixture was washed with water and the water and ether were distilled off to give a reddish-brown liquid as an alkyl salicylic acid. nuclear The magnetic analysis product contained 5-docosyl salicylic acid 97. 93%.

Reference： [1]Patent: CN106518647,2017,A .Location in patent: Paragraph 0027; 0028

58
[ 6938-66-5 ]
[ 99-76-3 ]
methyl 4-docosyloxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 16h;Inert atmosphere;	Under an argon atmosphere, potassium carbonate (1.36 g, 9.85 mmol), methyl 4-hydroxybenzoate (500 mg, 3.29 mmol), 1-bromooctadecane (1.28 g, 3.62 mmol) were dissolved in N,N-dimethylformamide (30 mL), and the mixture was stirred at 90 C. for 16 hr. Completion of the reaction was confirmed by thin layer chromatography, and the reaction solution was poured into water (400 mL) to allow for precipitation to give a solid. The obtained solid was dissolved in ethyl acetate (50 mL) at 70 C., cooled to room temperature to precipitate crystals, which were collected by filtration, and dried to give the object compound (1.37 g, 91%). 1H-NMR (400 MHz, CDCl3): delta=0.88 (t, 3H, J=6.8 Hz, -CH2CH2(CH2)15CH3), 1.26-1.58 (m, 38H, -CH2CH2 (CH2)19CH3), 1.76-1.83 (m, 2H, -CH2CH2(CH2)19CH3), 3.88 (s, 3H, -C(O)OCH3), 4.00 (t, 2H, J=6.4 Hz, -CH2CH2(CH2)15CH3), 6.90 (d, 2H, J=9.5 Hz, Ar-H), 7.98 (d, 2H, J=9.5 Hz, Ar-H)

Reference： [1]Patent: US2017/320904,2017,A1 .Location in patent: Paragraph 0547-0549

59
[ 1640-39-7 ]
[ 6938-66-5 ]
1-docosyl-3,3-dimethyl-2-methyleneindoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.093 g	With sodium iodide; In acetonitrile; at 150℃; for 0.666667h;Microwave irradiation;	A 20 mL microwave vial containing a stirbar was charged with 2,3,3-trimethylindolenine (2.5 mL, 15.6 mmol, 1.0 equiv), <strong>[6938-66-5]1-bromodocosane</strong> (7.894 g, 20.3 mmol, 1.30 equiv), sodium iodide (2.30 g, 15.3 mmol, 0.98 equiv) and 8 mL acetonitrile. The vial was placed in a Biotage Initiator Classic microwave reactor and held at 150 C for 40 minutes, and then cooled to room temperature. The contents of the vial were removed with ethyl acetate, added to a separatory funnel, and water added, resulting in an insoluble white solid. All layers were combined and the water and ethyl acetate removed under reduced pressure. The residue was dissolved methylene chloride, transferred to a separatory funnel and washed with water (1 x) and then with IN NaOH (3x). The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to yield dark red viscous liquid l-docosyl-3,3-dimethyl-2- methyleneindoline (9.093 g).

Reference： [1]Patent: WO2017/223413,2017,A1 .Location in patent: Paragraph 0084; 0092

60
[ 6938-66-5 ]
[ 70720-38-6 ]
3-methyl-N-(1-phenyltricosyl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium carbonate; In toluene; at 160℃; for 22h;Inert atmosphere; Sealed tube; Glovebox;	General procedure: Solid starting materials (except the catalyst) were placed in an oven-dried 8 cm3 glass vial with a solid top screw cap and a magnetic stirring bar. The vial was transferred into the glovebox under argon. Catalyst, liquid starting materials, solvent, and dodecane (as internal standard) were added inthe glove box. Finally, the vial was closed and the reaction mixture was heated in a heating block for the desired time at the desired temperature. General work-up procedure B for C-H activation reactions towards compounds 2-14 and 18-25 After cooling the reaction mixture to room temperature, the solid material was removed by filtration using a Pasteur pipette with cotton and Hyflo. The residue was washed withCH2Cl2. The combined organic filtrate was concentrated under reduced pressure. The resulting crude residue was purified by flash column chromatography (LP/EtOAc).

Reference： [1]Monatshefte fur Chemie,2019,vol. 150,p. 127 - 138

61
[ 6938-66-5 ]
[ 120-80-9 ]
1,2-didocosyloxybenzene [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2019,vol. 7,p. 1151 - 1163

62
[ 6938-66-5 ]
[ 100-79-8 ]
[ 171364-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In toluene;Inert atmosphere; Schlenk technique; Reflux;	General procedure: Sodium hydride (2 equivalents) was added portion-wise to a stirred solution of 1,2-isopropylideneglycerol 17 (1 equivalent) and the appropriate 1-bromoalkane (1 equivalent) in anhydrous toluene at rt. After addition was completed, the mixture was refluxed overnight, cooled to rt. Excess Sodium hydride was quenched via careful dropwise addition of water. The organic layer was dried, evaporated and used directly in the next step.

Reference： [1]Bioorganic Chemistry,2019,vol. 84,p. 51 - 62

63
[ 6938-66-5 ]
[ 5870-37-1 ]
dimethyl-2,5-didocosyloxy terephthalate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 8177 - 8189

64
[ 6938-66-5 ]
[ 634585-49-2 ]
4-benzyloxy-2,5-dibromo-1-docosyloxybenzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 2725 - 2729
Angew. Chem.,2020,vol. 132,p. 2747 - 2751,5

65
[ 104-92-7 ]
[ 6938-66-5 ]
[ 22161-92-8 ]

Reference： [1]Journal of Materials Chemistry C,2020,vol. 8,p. 3316 - 3336

66
[ 6938-66-5 ]
[ 2563-26-0 ]
1,2-dibromo-4,5-bis(docosyloxy)benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 5526 - 5530

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6938-66-5 ] {[proInfo.proName]}

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[ 6938-66-5 ] Synthesis Path-Upstream 1~4

[ 6938-66-5 ] Synthesis Path-Downstream 1~66

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Aliphatic Chain Hydrocarbons

Bromides

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[ 6938-66-5 ]