[ CAS No. 14174-08-4 ] {[proInfo.proName]}

Name: 14174-08-4|Benzo-12-crown-4|98%
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Quality Control of [ 14174-08-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 14174-08-4 ]

CAS No. :	14174-08-4	MDL No. :	MFCD00059934
Formula :	C₁₂H₁₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OAJNZFCPJVBYHB-UHFFFAOYSA-N
M.W :	224.25	Pubchem ID :	586075
Synonyms :

Safety of [ 14174-08-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 14174-08-4 ]

* 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 [ 14174-08-4 ]

[ 14174-08-4 ] Synthesis Path-Downstream 1~88

1
[ 50-00-0 ]
[ 14174-08-4 ]
[ 134767-38-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 1413 - 1415

3
[ 14174-08-4 ]
(4aR,14aS)-Dodecahydro-5,8,11,14-tetraoxa-benzocyclododecene [ No CAS ]

Reference： [1]Doklady Chemistry,1989,vol. 306,p. 171 - 173
Dokl. Akad. Nauk SSSR Ser. Khim.,1989,vol. 306,p. 876 - 878

4
[ 14174-08-4 ]
[ 126867-37-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 1803 - 1807
Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 1995 - 2000

5
[ 14174-08-4 ]
[ 78554-67-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With nitric acid; acetic acid; In chloroform; at 20℃; for 24h;Cooling with ice;	In a 100 mL round bottom flask, add the <strong>[14174-08-4]benzo-12-crown-4</strong> (2 mmol) prepared in step (2),10 mL of chloroform and 6 mL of acetic acid were slowly added to 4 mL of 68 wt% concentrated nitric acid under ice bath conditions, and after stirring at room temperature for 24 h,The reaction solution was neutralized with alkali, and the chloroform layer was separated. After the aqueous layer was extracted with chloroform, the combined chloroform layer was dried over anhydrous magnesium sulfate.The chloroform was distilled off under reduced pressure to obtain a yellow crude product, which was separated by column chromatography.Elution with (V ethyl acetate: V petroleum ether = 1: 2), compound III (4-nitro<strong>[14174-08-4]benzo-12-crown-4</strong>) was obtained with a yield of 75%;
59%	With nitric acid; In acetonitrile;Reflux;	To a refluxing solution of 6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzo- cyclododecene (6.50 g, 28.98 mmol) in 65 mL of acetonitrile, was added nitric acid (56%, 5.4 mL) dropwise. When TLC showed the completion of reaction, 160 mL of water was added. The resulting solution was kept at 2 C overnight. The precipitate was collected and washed until to neutral pH, giving desired 2-Nitro-6,7,9,10,12,13-hexahydro-5,8,l l,14- tetraoxa-benzocyclododecene as yellow solid (4.61 g, 59% yield).
	With nitric acid; In water; acetonitrile; at 85℃; for 0.5h;	A solution of compound 31-2 (50 mg, 222.96 mmol, 1 eq) in acetonitrile (2 mL) was warmed up to 85C.Concentrated nitric acid (38 mg, 337.71 mmol, 27.14 mL, 56% purity, 1.51 eq) was slowly added dropwisely. After thecompletion of the dropwise addition, the mixture was stirred at 85C for 0.5 hour. The reaction mixture was cooled toroom temperature and poured into ice (about 10 mL) to quench the reaction. The mixture was extracted with ethyl acetate(3x10 mL). The above organic phases were combined, dried over anhydrous sodium sulfate and filtered. The filtratewas concentrated under reduced pressure to give compound 31-3, which was directly used in the next step without theneed for any further purification. 1H NMR (400 MHz, CDCl3) δppm 7.86-7.89 (m, 1 H), 7.81 (d, J=2.8 Hz, 1H), 6.93 (d,J=8.8Hz, 1H), 4.17-4.23 (m, 4H), 3.84-3.85 (m, 2H), 3.77-3.80 (m, 2H), 3.71 (s, 4H).

Reference： [1]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 1527 - 1532
[2]Dalton Transactions,2007,p. 2915 - 2924
[3]Patent: CN110746423,2020,A .Location in patent: Paragraph 0012
[4]Synthetic Communications,1981,vol. 11,p. 323 - 328
[5]Patent: WO2019/46163,2019,A1 .Location in patent: Paragraph 00233
[6]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 147 - 148
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 182 - 183
[7]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044
[8]Russian Journal of Organic Chemistry,1998,vol. 34,p. 1517 - 1518
[9]Zeitschrift fur Naturforschung, B: Chemical Sciences,2011,vol. 66,p. 923 - 929
[10]Patent: EP3686204,2020,A1 .Location in patent: Paragraph 0301; 0304-0305

6
[ 14174-08-4 ]
[ 118409-81-7 ]

Reference： [1]Journal of Organometallic Chemistry,1988,vol. 346,p. 267 - 276
[2]Journal of Organic Chemistry,2000,vol. 65,p. 2870 - 2874

7
[ 14174-08-4 ]
[ 100-97-0 ]
[ 84993-16-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 957 - 963
Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 1063 - 1070

8
[ 14174-08-4 ]
[ 108-24-7 ]
[ 107996-83-8 ]

Reference： [1]Synthesis,1986,p. 680 - 683

9
[ 120-80-9 ]
[ 112-26-5 ]
[ 14174-08-4 ]

Yield	Reaction Conditions	Operation in experiment
14.4%	With lithium hydroxide monohydrate; In water; butan-1-ol; at 95℃;Inert atmosphere;	Under nitrogen, to the mixture of (22.02 g, 199.98 mmol) in 220 mL of n- butanol, was added 46 mL of aqueous solution of LiOH H2O (18.46 g, 439.94 mmol). The mixture was heated to 95 C, followed by addition of l-chloro-2-[2-(2-chloro-ethoxy)-ethoxy] -ethane (37.43 g, 200.09 mmol) in 240 mL of n-butanol. The reaction was heated overnight, then filtrated. 1 M of aqueous hydrochloric acid was added to adjust pH to 8. After removal of most n-butanol under reduced pressure, the residue was extracted with dichloromethane 250 mL x 2. The combined organic layer was washed with brine and dried over anhydrous MgSCH. The crude product was purified by column chromatography on silica gel, giving 6.5 g of 6,7,9,10,12,13-Hexahydro- 5,8,11,14-tetraoxa-benzocyclododecene as yellow oil, 14.4% yield.

Reference： [1]Patent: WO2019/46163,2019,A1 .Location in patent: Paragraph 00232
[2]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 957 - 963
Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 1063 - 1070
[3]Synthetic Communications,1981,vol. 11,p. 323 - 328

10
[ 120-80-9 ]
[ 112-26-5 ]
[ 14174-08-4 ]
[ 14174-09-5 ]

Reference： [1]Dalton Transactions,2007,p. 2915 - 2924
[2]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 147 - 148
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 182 - 183
[3]Journal of the American Chemical Society,1982,vol. 104,p. 1960 - 1967

11
[ 120-80-9 ]
[ 19249-03-7 ]
[ 14174-08-4 ]

Yield	Reaction Conditions	Operation in experiment
52%		In a 100 ml flask, dissolve catechol (5 mmol) and 2.5 mmol of tetrabutylammonium bromide (TBAB) in 30 mL of a toluene solution, and then add a 50 wt% aqueous NaOH solution (10 mL).Stir the mixture at 50-60 C for 30 minutes, and then add (30 mL) containing triethylene glycol di-p-toluenesulfonate (5 mmol, also known as triethylene glycol bis (p-toluenesulfonate)) Of toluene solution.The resulting mixture was stirred vigorously at this temperature under reflux for 16 h.After the reaction,The organic layer was separated with H 2 O (3 × 200 mL), washed with saturated brine, and dried over MgSO 4.The solvent was removed in vacuo and the residue was extracted with ethyl acetate (3 × 50 mL).After cooling, the product was separated by column chromatography and eluted with (V ethyl acetate: V petroleum ether = 2: 1) to obtain compound II (benzo-12-crown-4) with a yield of 52%;
28%		Mix 2.2kg (20mol) catechol, 12.4kg (89.6mol) potassium carbonate and 300L DMF, stir for about 30min., heat up to 85-90C, add prepared 1,8-bis(p-toluenesulfonate)-3,6-dioxoctane(2) by dropping 40L of 9.17kg (20mol) DMF solution, drip in 1.5-2h, drip and react for 30min., TLC check the reaction is completed (developing solvent: petroleum ether: ethyl acetate=1:1, Rf=0.58) . Aspirate about 40L of the reaction liquid, continue to repeat the above operation 3 to 5 times, filter with suction, evaporate DMF under reduced pressure, dissolve the residue with 240L of ethyl acetate, filter with suction, and distill under reduced pressure, and use petroleum ether: ethyl acetate = 1:1 for column chromatography. The solvent was recovered under reduced pressure, and the solid was recrystallized with isopropanol 1:2.5 (W/V) to obtain 1.376 kg of off-white powder with a yield of 28%.

Reference： [1]Patent: CN110746423,2020,A .Location in patent: Paragraph 0012
[2]Patent: CN111233820,2020,A .Location in patent: Paragraph 0023; 0033-0040
[3]Synthesis,2002,p. 2266 - 2270
[4]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 3044 - 3046

12
[ 77963-44-1 ]
[ 14174-08-4 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 4142 - 4145
[2]Journal of the American Chemical Society,1981,vol. 103,p. 4142 - 4145

13
[ 14174-08-4 ]
[ 64-19-7 ]
[ 107996-83-8 ]
2,3-(4,5-diacetyl)benzo-12-crown-4 ether [ No CAS ]

Reference： [1]Journal of applied chemistry of the USSR,1986,vol. 59,p. 1514 - 1515
[2]Journal of applied chemistry of the USSR,1986,vol. 59,p. 1514 - 1515

14
[ 14174-08-4 ]
[ 802294-64-0 ]
1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-propan-1-one [ No CAS ]
1-(3-Propionyl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-propan-1-one [ No CAS ]

Reference： [1]Journal of applied chemistry of the USSR,1986,vol. 59,p. 1514 - 1515
[2]Journal of applied chemistry of the USSR,1986,vol. 59,p. 1514 - 1515

15
[ 87494-76-6 ]
[ 14174-08-4 ]

Reference： [1]Journal of the American Chemical Society,1984,vol. 106,p. 168 - 174

16
[ 14174-08-4 ]
[ 75-65-0 ]
[ 98987-34-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 1313 - 1314
Khimiya Geterotsiklicheskikh Soedinenii,1990,p. 1572 - 1573
[2]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 1313 - 1314
Khimiya Geterotsiklicheskikh Soedinenii,1990,p. 1572 - 1573

17
[ 14174-08-4 ]
[ 107-92-6 ]
1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-butan-1-one [ No CAS ]
1-(3-Butyryl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-butan-1-one [ No CAS ]

Reference： [1]Journal of applied chemistry of the USSR,1986,vol. 59,p. 1514 - 1515
[2]Journal of applied chemistry of the USSR,1986,vol. 59,p. 1514 - 1515

18
[ 14174-08-4 ]
[ 109-52-4 ]
1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-pentan-1-one [ No CAS ]
1-(3-Pentanoyl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-pentan-1-one [ No CAS ]

Reference： [1]Journal of applied chemistry of the USSR,1986,vol. 59,p. 1514 - 1515
[2]Journal of applied chemistry of the USSR,1986,vol. 59,p. 1514 - 1515

19
[ 14174-08-4 ]
[ 768-95-6 ]
2-Adamantan-1-yl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecene [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,1996,vol. 32,p. 810 - 812

20
[ 14174-08-4 ]
3'-sulfobenzo-12-crown-4 [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 371 - 377
[2]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 822 - 826

21
[ 1120-99-6 ]
[ 14174-08-4 ]
5-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-2,5-dihydro-[1,2,4]triazin-3-ylamine [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,1999,vol. 35,p. 1253 - 1254

22
[ 14174-08-4 ]
[ 54673-30-2 ]
[ 407-25-0 ]
4-(5-Oxo-1-trifluoroacetyl-3-phenyl-1,2,5,6-tetrahydro-1,2,4-triazin-6-yl)benzo-12-crown-4 [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,1999,vol. 35,p. 1253 - 1254

23
[ 14174-08-4 ]
[ 78554-67-3 ]
4',5'-dinitro-B₁₂C₄ [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 1449 - 1456

24
[ 14174-08-4 ]
1-acetyl-3-phenyl-1,6-dihydro-4H-[1,2,4]triazin-5-one [ No CAS ]
3-(1-acetyl-5-oxo-3-phenyl-1,4,5,6-tetrahyro-1,2,4-triazin-6-yl)benzo-12-crown-4 [ No CAS ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359

25
[ 14174-08-4 ]
1-acetyl-3-p-tolyl-1,6-dihydro-4H-[1,2,4]triazin-5-one [ No CAS ]
[ 420118-24-7 ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359

26
[ 14174-08-4 ]
[ 89179-74-8 ]
[ 407-25-0 ]
3-Ethylsulfanyl-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one [ No CAS ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359

27
[ 14174-08-4 ]
[ 54673-30-2 ]
[ 407-25-0 ]
6-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-phenyl-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one [ No CAS ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359

28
[ 14174-08-4 ]
[ 36993-93-8 ]
[ 407-25-0 ]
[ 420118-14-5 ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359

29
[ 14174-08-4 ]
3-(4-Chlorophenyl)-2H-1,2,4-triazin-5-one [ No CAS ]
[ 407-25-0 ]
3-(4-Chloro-phenyl)-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one [ No CAS ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359

30
[ 10234-40-9 ]
[ 6315-52-2 ]
[ 14174-08-4 ]

Reference： [1]Synthesis,2002,p. 2266 - 2270

31
[ 54535-06-7 ]
[ 107-21-1 ]
[ 14174-08-4 ]

Reference： [1]Synthesis,2002,p. 2266 - 2270

32
[ 99700-26-2 ]
[ 14174-08-4 ]

Reference： [1]Synthesis,2002,p. 2266 - 2270

33
[ 14174-08-4 ]
[ 2032-35-1 ]
C₂₆H₃₃BrO₈ [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 843 - 854

34
[ 50-00-0 ]
[ 14174-08-4 ]
[ 906096-99-9 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4091 - 4095

35
[ 14174-08-4 ]
[ 78554-68-4 ]

Reference： [1]Dalton Transactions,2007,p. 2915 - 2924
[2]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 1527 - 1532
[3]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044
[4]Synthetic Communications,1981,vol. 11,p. 323 - 328
[5]Chemistry of Heterocyclic Compounds,1985,vol. 21,p. 147 - 148
Khimiya Geterotsiklicheskikh Soedinenii,1985,vol. 21,p. 182 - 183
[6]Zeitschrift fur Naturforschung, B: Chemical Sciences,2011,vol. 66,p. 923 - 929
[7]Patent: WO2019/46163,2019,A1
[8]Patent: CN110746423,2020,A
[9]Patent: EP3686204,2020,A1

36
[ 14174-08-4 ]
C₅₆H₅₆O₁₀ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4091 - 4095

37
[ 14174-08-4 ]
[ 124362-37-4 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 957 - 963
Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 1063 - 1070

38
[ 120-80-9 ]
[ 14174-08-4 ]

Reference： [1]Synthesis,2002,p. 2266 - 2270

39
[ 111875-70-8 ]
[ 14174-08-4 ]

Reference： [1]Synthesis,2002,p. 2266 - 2270

40
[ 14174-08-4 ]
N-(2,3,5,6,8,9-hexahydro-1,4,7,10-benzotetraoxacyclododecin-12-yl)-4-(1-pyrenyl)butyramide [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 1527 - 1532

41
[ 14174-08-4 ]
3-(5-oxo-phenylamino-2,5-dihydro-1,2,4-triazin-6-yl)benzo-12-crown-4 [ No CAS ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359

42
[ 14174-08-4 ]
6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-p-tolyl-2H-[1,2,4]triazin-5-one [ No CAS ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359
[2]Heterocycles,2001,vol. 55,p. 2349 - 2359
[3]Heterocycles,2001,vol. 55,p. 2349 - 2359

43
[ 14174-08-4 ]
[ 420118-28-1 ]

Reference： [1]Heterocycles,2001,vol. 55,p. 2349 - 2359

44
[ 14174-08-4 ]
4-(3-Amino-1,2,4-triazin-5-yl)benzo-12-crown-4 [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,1999,vol. 35,p. 1253 - 1254

45
[ 14174-08-4 ]
[ 264142-13-4 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 2870 - 2874

46
[ 14174-08-4 ]
bis(2-nitro-4,5-(1,4,7,10-tetraoxadecamethylene)phenyl) disulfide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 2870 - 2874

47
[ 14174-08-4 ]
bis(2-nitro-4,5-(1,4,7,10-tetraoxadecamethylene)phenyl) diselenide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 2870 - 2874

48
[ 14174-08-4 ]
[ 167300-08-5 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044

49
[ 14174-08-4 ]
(1S,5R,7S)-3-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carbonyl chloride [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044

50
[ 14174-08-4 ]
(1S,5R,7S)-3-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044

51
[ 14174-08-4 ]
(1R,5S,7R)-3-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid (6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044
[2]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044

52
[ 14174-08-4 ]
(1R,5S,7R)-3-(6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid (6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044

53
[ 14174-08-4 ]
(1R,5S,7R)-3-(6,7,9,10,12,13,15,16,18,19-Decahydro-5,8,11,14,17,20-hexaoxa-benzocyclooctadecen-2-yl)-2,4-dioxo-1,5,7-tripropyl-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid (6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 7041 - 7044

54
[ 14174-08-4 ]
[ 120434-45-9 ]

Reference： [1]Journal of Organometallic Chemistry,1988,vol. 346,p. 267 - 276

55
[ 14174-08-4 ]
4'-picrylamino benzo-12-crown-4 [ No CAS ]

Reference： [1]Synthetic Communications,1981,vol. 11,p. 323 - 328

56
[ 14174-08-4 ]
[ 109789-52-8 ]

Reference： [1]Synthesis,1986,p. 680 - 683

57
[ 14174-08-4 ]
[ 109789-47-1 ]

Reference： [1]Synthesis,1986,p. 680 - 683

58
[ 31255-10-4 ]
[ 14174-08-4 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 4142 - 4145

59
[ 112-27-6 ]
[ 14174-08-4 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 4142 - 4145
[2]Patent: CN110746423,2020,A
[3]Patent: CN111233820,2020,A

60
tantalum(V) oxide [ No CAS ]
[ 14174-08-4 ]
[ 7664-39-3 ]
[ 7732-18-5 ]
[(benzo-12-crown-4)2*H₃O][TaF₆] [ No CAS ]

Reference： [1]Polyhedron,2007,vol. 26,p. 5193 - 5202

61
[ 14174-08-4 ]
[ 7783-71-3 ]
[ 7664-39-3 ]
[ 7732-18-5 ]
[(benzo-12-crown-4)2*H₃O][TaF₆] [ No CAS ]

Reference： [1]Polyhedron,2007,vol. 26,p. 5193 - 5202

62
[ 14174-08-4 ]
[ 2032-35-1 ]
C₂₆H₃₂O₈ [ No CAS ]

Reference： [1]Synthetic Communications,2015,vol. 45,p. 488 - 494
[2]Russian Chemical Bulletin,2008,vol. 57,p. 793 - 801

63
[ 10544-50-0 ]
[ 14174-08-4 ]
sodium amalgam [ No CAS ]
(K[Mo⁽¹³⁾C(N(CH₃(C⁽²⁾H₃)2C)(C₆H₃(CH₃)2))3])2 [ No CAS ]
Na⁽¹⁺⁾*2(C₄H₄(C₂O)(C₂H₄O)3)*[Mo⁽¹³⁾CS(N(CH₃(C⁽²⁾H₃)2C)(C₆H₃(CH₃)2))3]^(1-)=[Na(C₂₄H₃₂O₈)][Mo⁽¹³⁾CS(N(C₄H₃⁽²⁾H₆)(C₈H₉))3] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 5003 - 5013

64
[ 14174-08-4 ]
[ 121669-21-4 ]
C₂₄H₃₂LiO₈⁽¹⁺⁾*ClO₄^(1-) [ No CAS ]

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2010,vol. 68,p. 431 - 436

65
[ 14174-08-4 ]
[ 1340516-50-8 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2011,vol. 66,p. 923 - 929

66
[ 1121-60-4 ]
[ 14174-08-4 ]
[ 1366625-26-4 ]

Yield	Reaction Conditions	Operation in experiment
49%	With trifluorormethanesulfonic acid; In chloroform; at 25℃;	General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1701 - 1704

67
[ 14174-08-4 ]
[ 611-09-6 ]
[ 1366625-22-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With trifluorormethanesulfonic acid; In chloroform; at 25℃;	General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1701 - 1704

68
[ 14174-08-4 ]
[ 485-47-2 ]
[ 1366625-24-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sulfuric acid; In chloroform; at 25℃;	General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1701 - 1704

69
[ 14174-08-4 ]
[ 111380-75-7 ]
[ 1380508-63-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With polyphosphoric acid; at 80 - 85℃; for 0.5h;	General procedure: 4.2.1. Method A. molecular clip 2 was obtained in 50% yield as described6b Method B. A mixture of bisether 8 (1 g, 2.65 mmol) and corresponding benzocrown ether (5.42 mmol) in PPA (30 g) was stirred vigorously at 80-85 for 30 min. A deep purple color was formed in 5 min. To the cooled reaction mixture was added water (150 mL) and product was extracted with CHCl3 (3×50 mL). The organic layer was washed with water until neutral (∼3×50 mL) and subjected to azeotropic drying. The solvent was removed at reduced pressure and the residue was dissolved in a mixture of CHCl3/MeOH (50:1, 100 mL) and filtered through SiO2 (~30 mL). The solvent was removed at reduced pressure and the crude product was purified as described below. Method C. The procedure is similar to Method B, with exception that tetraol 9 (1.1 g, 2.65 mmol) was used instead bisether 8. Method D. A suspension of NaH (0.288 g, 12 mmol) in DMSO (26 mL) was heated with stirring at 70 for 30 min. The resulting mixture was cooled to room temperature and a solution of 11 (0.78 g, 2.65 mmol) in DMSO (40 mL) was added. Stirring was continued for 20 min and then solution of 10 (5.92 g, 5.83 mmol) in DMSO (40 mL) was added dropwise over 5 min and the resulting mixture was stirred at room temperature for 24 h. The mixture was poured into ice water (400 mL) and acidified with HCl to pH~2. The resulting solid was filtered off, washed with water (3×50 mL). The crude product was purified as described below.

Reference： [1]Tetrahedron,2012,vol. 68,p. 4757 - 4764
[2]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2014,vol. 79,p. 343 - 348

70
[ 14174-08-4 ]
[ 101241-22-9 ]
[ 1380508-63-3 ]

Yield	Reaction Conditions	Operation in experiment
36%	With polyphosphoric acid; at 80 - 85℃; for 0.5h;	General procedure: 4.2.1. Method A. molecular clip 2 was obtained in 50% yield as described6b Method B. A mixture of bisether 8 (1 g, 2.65 mmol) and corresponding benzocrown ether (5.42 mmol) in PPA (30 g) was stirred vigorously at 80-85 for 30 min. A deep purple color was formed in 5 min. To the cooled reaction mixture was added water (150 mL) and product was extracted with CHCl3 (3×50 mL). The organic layer was washed with water until neutral (∼3×50 mL) and subjected to azeotropic drying. The solvent was removed at reduced pressure and the residue was dissolved in a mixture of CHCl3/MeOH (50:1, 100 mL) and filtered through SiO2 (~30 mL). The solvent was removed at reduced pressure and the crude product was purified as described below. Method C. The procedure is similar to Method B, with exception that tetraol 9 (1.1 g, 2.65 mmol) was used instead bisether 8. Method D. A suspension of NaH (0.288 g, 12 mmol) in DMSO (26 mL) was heated with stirring at 70 for 30 min. The resulting mixture was cooled to room temperature and a solution of 11 (0.78 g, 2.65 mmol) in DMSO (40 mL) was added. Stirring was continued for 20 min and then solution of 10 (5.92 g, 5.83 mmol) in DMSO (40 mL) was added dropwise over 5 min and the resulting mixture was stirred at room temperature for 24 h. The mixture was poured into ice water (400 mL) and acidified with HCl to pH~2. The resulting solid was filtered off, washed with water (3×50 mL). The crude product was purified as described below.

Reference： [1]Tetrahedron,2012,vol. 68,p. 4757 - 4764

71
[ 55400-73-2 ]
[ 120-80-9 ]
[ 14174-08-4 ]

Reference： [1]ARKIVOC,2010,vol. 2010,p. 238 - 248

72
[ 14174-08-4 ]
C₂₆H₃₀O₁₀ [ No CAS ]

Reference： [1]Synthetic Communications,2015,vol. 45,p. 488 - 494

73
[ 14174-08-4 ]
C₃₆H₄₂O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.6%	With iron(III) chloride; dipotassium peroxodisulfate; at 10 - 15℃; for 2h;	500 ml of propylene carbonate was added into 1000 ml four-necked flask, potassium peroxodisulfate 116.2g (0.43mmol) and <strong>[14174-08-4]benzo-12-crown-4</strong> ether 96.4g (0.43mmol) were added, stirred, and cooled at internal temperature of 10 degrees C. Anhydrous iron(III) chloride 276.3g (1.68mmol) was added little by little, reacted with the internal temperature of 10-15 degrees C for 2 hours. 2000 ml of water was added after completion of reaction, cooled, and stirred for 10 minutes. The aqueous layer of the solution was separated, and the organic layer was washed with 200 ml of 1N hydrochloric acid aqueous solution. The aqueous layer was removed and the organic layer was washed with 500 ml of salt solution. 600 ml of methanol was added to the organic layer, and crystallized for 1 hour at an internal temperature of 15-25 degrees C. The crystals were dried and obtained 72.2 g (75.6% of yield) as thin purple crystal. It checked that the product was synthesized with the mass spectrum and the NMR spectrum.

Reference： [1]Patent: JP5731346,2015,B2 .Location in patent: Paragraph 0089

74
[ 14174-08-4 ]
1-[3-[[5-fluoro-2-(2,5,8,11-tetraoxabicyclo[10.4.0]hexadeca-1⁽¹²⁾,13,15-trien-14-ylamino)pyrimidin-4-yl]amino]-1-piperidyl]prop-2-en-1-one [ No CAS ]

Reference： [1]Patent: WO2019/46163,2019,A1

75
[ 14174-08-4 ]
12-(pyren-1-ylethynyl)-2,3,5,6,8,9-hexahydrobenzo[b][1,4,7,10]tetraoxacyclododecin [ No CAS ]