Name: 23978-55-4|1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane|98%
Brand: Ambeed
SKU: A785615
Price: 24.0 USD
Availability: InStock
Rating: 95 (22 reviews)

1
[ 69703-25-9 ]
[ 23978-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;	Compound 2 was obtained by hydrogenolysis15 of N,N′-dibenzyl-4,13-diaza-18-crown-6 (4).

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1994,p. 513 - 520
[2]Journal of the American Chemical Society,1984,vol. 106,p. 8240 - 8244
[3]Organic Syntheses,1990,vol. 68,p. 227 - 227
[4]Australian Journal of Chemistry,1999,vol. 52,p. 1109 - 1114
[5]Tetrahedron Letters,1986,vol. 27,p. 327 - 330
[6]Synthesis,2014,vol. 46,p. 2771 - 2779
[7]Chemical Communications,2017,vol. 53,p. 4258 - 4261

2
[ 2382-10-7 ]
[ 23978-55-4 ]
C₂₄H₃₂Cl₂N₁₀O₄ [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1992,vol. 26,p. 745 - 747
Khimiko-Farmatsevticheskii Zhurnal,1992,vol. 26,p. 66 - 68

3
[ 100-44-7 ]
[ 23978-55-4 ]
[ 69703-25-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide In chloroform; water Ambient temperature; overnight;
60%	With sodium hydroxide In chloroform; water Ambient temperature;

Reference： [1]Tsukube, Hiroshi [Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 9, p. 2685 - 2686]
[2]Tsukube, Hiroshi; Takagi, Kentaro; Higashiyama, Tatsuo; Iwachido, Tadashi; Hayama, Naomi [Journal of the Chemical Society. Perkin transactions I, 1986, p. 1033 - 1038]
[3]Tsukube, Hiroshi; Yamashita, Kouichi; Iwachido, Tadashi; Zenki, Michio [Tetrahedron Letters, 1988, vol. 29, # 5, p. 569 - 572]

4
[ 25711-25-5 ]
[ 23978-55-4 ]
[ 147688-19-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 21 - 26

5
[ 4206-61-5 ]
[ 23978-55-4 ]
[ 129940-65-4 ]

Yield	Reaction Conditions	Operation in experiment
23%	In tetrahydrofuran; ethanol for 10h; Heating;

Reference： [1]Luk'yanenko, N. G.; Reder, A. S. [Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 2.2, p. 343 - 352][Zhurnal Organicheskoi Khimii, 1989, vol. 25, # 2, p. 385 - 394] Lukyanenko, Nikolay G.; Reder, Anatoly S. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 2533 - 2536]

6
[ 627-42-9 ]
[ 23978-55-4 ]
[ 72911-99-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 89 - 93

7
[ 34270-90-1 ]
[ 23978-55-4 ]
[ 142030-19-1 ]

Reference： [1]Bulletin of the Polish Academy of Sciences: Chemistry,1991,vol. 39,p. 275 - 277

8
[ 34680-81-4 ]
[ 23978-55-4 ]
[ 144102-75-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; sodium iodide In acetonitrile for 72h; Heating;

Reference： [1]Kataky, Ritu; Parker, David; Teasdale, Andrew; Hutchinson, Jonathan P.; Buschmann, Hans-J. [Journal of the Chemical Society. Perkin transactions II, 1992, # 8, p. 1347 - 1351]

9
[ 5105-78-2 ]
[ 23978-55-4 ]
[ 93767-93-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;
87%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h;

Reference： [1]Luk'yanenko, N. G.; Bogatskii, A. V.; Voronina, T. A.; Golovenko, N. Ya.; Karaseva, T. L.; et al. [Pharmaceutical Chemistry Journal, 1985, vol. 19, # 6, p. 403 - 405][Khimiko-Farmatsevticheskii Zhurnal, 1985, vol. 19, # 6, p. 691 - 693]
[2]Luk'yanenko, N. G.; Bogat-skii, A. V.; Basok, S. S.; Ostrovskaya, L. K.; Nazarova, N. Yu.; Karpenko, L. P. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1438 - 1444][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 7, p. 1580 - 1587]

10
[ 1685-33-2 ]
[ 23978-55-4 ]
(R,R)-bis(N-benzyloxycarbonylvalyl)diaza-18-crown-6 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h;

Reference： [1]Luk'yanenko, N. G.; Bogat-skii, A. V.; Basok, S. S.; Ostrovskaya, L. K.; Nazarova, N. Yu.; Karpenko, L. P. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1438 - 1444][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 7, p. 1580 - 1587]

11
[ 28862-79-5 ]
[ 23978-55-4 ]
[ 93788-24-0 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1438 - 1444
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1580 - 1587

12
[ 7598-10-9 ]
[ 23978-55-4 ]
[ 127645-80-1 ]

Reference： [1]Chemische Berichte,1990,vol. 123,p. 1673 - 1677

13
[ 14704-31-5 ]
[ 23978-55-4 ]
N,N'-Bis((biphenyl-3-yl)methyl)diaza-18-crown-6 [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 4389 - 4397

14
[ 17609-52-8 ]
[ 23978-55-4 ]
[ 91598-89-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 20h;

Reference： [1]Luk'yanenko, N. G.; Bogat-skii, A. V.; Basok, S. S.; Ostrovskaya, L. K.; Nazarova, N. Yu.; Karpenko, L. P. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1438 - 1444][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 7, p. 1580 - 1587]

15
[ 3747-74-8 ]
[ 23978-55-4 ]
[ 130985-63-6 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 268 - 272

16
[ 130536-69-5 ]
[ 23978-55-4 ]
2-{2-[2-(16-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethyl}-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadec-7-yl)-ethoxy]-ethoxy}-ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium carbonate In 1,4-dioxane

Reference： [1]Nabeshima, Tatsuya; Inaba, Tadashi; Sagae, Takahiro; Furukawa, Naomichi [Tetrahedron Letters, 1990, vol. 31, # 27, p. 3919 - 3922]

17
[ 83478-63-1 ]
[ 23978-55-4 ]
[ 144809-29-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-ethyl-N,N-diisopropylamine In ethanol Heating;

Reference： [1]Tsukube, Hiroshi; Uenishi, Jun'ichi; Higaki, Hiromi; Kikkawa, Ken'ichi; Tanaka, Takakazu; et al. [Journal of Organic Chemistry, 1993, vol. 58, # 16, p. 4389 - 4397]

18
[ 23978-55-4 ]
[ 111-64-8 ]
[ 105400-02-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium carbonate; In benzene; at 20℃; for 16.5h;	[0102] N,N’-Dioctanoyl-<strong>[23978-55-4]4,13-diaza-18-crown-6</strong>. This compound was prepared by methods known in the art. To a mixture of <strong>[23978-55-4]4,13-diaza-18-crown-6</strong> (1.2 g, 4.6 mmol) and Na2CO3 (1.4 g, 13 mmol) in benzene (35 mL) was added octanoyl chloride (1.6 g, 9.8 mmol) in benzene (25 mL) over 30 mm and then stirred ambient temperature for an additional 16 h. The mixture was filtered and the solvent evaporated in vacuo. The lariat ether amide was obtained crystallization from hexanes in 71% yield as a white solid (mp 54.5-55 C).

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 5373 - 5384
[2]Patent: WO2016/22991,2016,A1 .Location in patent: Paragraph 0102

19
[ 23978-55-4 ]
[ 117330-41-3 ]
[ 117441-50-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium carbonate In acetonitrile for 15h; Heating;

Reference： [1]Alpha, Beatrice; Anklam, Elke; Deschenaux, Robert; Lehn, Jean-Marie; Pietraskiewicz, Marek [Helvetica Chimica Acta, 1988, vol. 71, p. 1042 - 1052]

20
[ 23978-55-4 ]
[ 2351-36-2 ]
[ 75359-90-9 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 941 - 944

21
[ 23978-55-4 ]
[ 2351-37-3 ]
[ 69909-28-0 ]
[ 90653-18-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 0.43 g	With triethylamine In dichloromethane for 16h;

Reference： [1]Hamilton,A.; Lehn,J.M.; Sessler,J.L. [Journal of the American Chemical Society, 1986, vol. 108, p. 5158]

22
[ 23978-55-4 ]
[ 74-88-4 ]
[ 31255-13-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium hydroxide In toluene for 4h; Ambient temperature; Irradiation;

Reference： [1]Jurczak, Janusz; Ostaszewski, Ryszard [Tetrahedron Letters, 1988, vol. 29, # 8, p. 959 - 960]

23
[ 23978-55-4 ]
[ 2279-15-4 ]
[ 93822-19-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1438 - 1444
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1580 - 1587

24
[ 7496-46-0 ]
[ 23978-55-4 ]
[ 160096-56-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 1 - 9
[2]Journal of the Chemical Society, Dalton Transactions,1994,p. 3325 - 3328

25
[ 100-39-0 ]
[ 23978-55-4 ]
[ 69703-25-9 ]
[ 94605-71-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 33% 2: 18%	With sodium carbonate; potassium iodide In various solvent(s) for 24h; Heating;

Reference： [1]Murillo, Oscar; Watanabe, Shigeru; Nakano, Akio; Gokel, George W. [Journal of the American Chemical Society, 1995, vol. 117, # 29, p. 7665 - 7679]

26
[ 2595-90-6 ]
[ 23978-55-4 ]
N,N'-bis(1-pyrenylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Reference： [1]Chemistry Letters,1996,p. 959 - 960
[2]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 3041 - 3046

27
[ 149817-62-9 ]
[ 23978-55-4 ]
[ 185506-09-6 ]
[ 185506-10-9 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 4249 - 4255

28
[ 149817-62-9 ]
[ 23978-55-4 ]
[ 185506-10-9 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 4249 - 4255

29
[ 50-00-0 ]
[ 23978-55-4 ]
[ 31255-13-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With formic acid In water at 80 - 90℃; for 24h;

Reference： [1]Solov'ev, Vitally P.; Strakhova, Nadezhda N.; Kazachenko, Vladimir P.; Solotnov, Alexandr F.; Baulin, Vladimir E.; Raevsky, Oleg A.; Ruediger, Volker; Eblinger, Frank; Schneider, Hans-Joerg [European Journal of Organic Chemistry, 1998, # 7, p. 1379 - 1389]

30
[ 16644-30-7 ]
[ 23978-55-4 ]
7,16-bis(2-hydroxy-3-formyl-5-nitrobenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1999,p. 199 - 204

31
[ 18592-13-7 ]
[ 23978-55-4 ]
7,16-bis(uracil-6-ylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctane [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 771 - 775

32
[ 50-00-0 ]
[ 1806-26-4 ]
[ 23978-55-4 ]
7,16-bis(2-hydroxy-5-octylbenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In toluene at 110℃; for 20h;

Reference： [1]Su, Ning; Bradshaw, Jerald S.; Savage, Paul B.; Krakowiak, Krzysztof E.; Izatt, Reed M.; De Wall, Stephen L.; Gokel, George W. [Tetrahedron, 1999, vol. 55, # 32, p. 9737 - 9742]

33
[ 50-00-0 ]
[ 29799-07-3 ]
[ 23978-55-4 ]
7,16-bis(5-(1'-adamantyl)-2-hydroxybenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 9737 - 9742

34
[ 50-00-0 ]
[ 978-86-9 ]
[ 23978-55-4 ]
7,16-bis(2-hydroxy-5-tritylbenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In toluene at 110℃; for 20h;

Reference： [1]Su, Ning; Bradshaw, Jerald S.; Savage, Paul B.; Krakowiak, Krzysztof E.; Izatt, Reed M.; De Wall, Stephen L.; Gokel, George W. [Tetrahedron, 1999, vol. 55, # 32, p. 9737 - 9742]

35
[ 50-00-0 ]
[ 5541-67-3 ]
[ 23978-55-4 ]
7,16-bis(5-methyl-8-hydroxyquinoline-7-ylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene; for 2.0h;Microwave irradiation;Product distribution / selectivity;	Following the procedure reported in Example 2 and using 5- methyl-8-hydroxy-quinoline (3b, 1.0 mmol, 0.159 g synthetized according to J. H. Burckhalter , R. I. Leib J. Org. Chem. 1961, 26, 4078-4083), 4b has been obtained as a pale yellow solid in 99percent yield (0.30 g, 0.49 mmol), and with a purity higher than 95percent, as judged by 1H- MR analysis. Example 5Following the procedure reported in Example 1 and using 5- chloro-8-hydroxy-quinoline (3c, 1.0 mmol , 0.18 g - Sigma Aldrich) , 4c has been obtained as a pale yellow solid in 96percent yield (0.31 g, 0.48 mmol), and with a purity higher than 95percent, as judged by ''"H-NMR analysis.

Reference： [1]Patent: WO2011/77226,2011,A1 .Location in patent: Page/Page column 21
[2]Journal of Organic Chemistry,2010,vol. 75,p. 6275 - 6278
[3]Journal of Organic Chemistry,1999,vol. 64,p. 8855 - 8861

36
[ 50-00-0 ]
[ 15450-76-7 ]
[ 23978-55-4 ]
7,16-bis(2,8-quinolinediol-7-ylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 8855 - 8861

37
[ 375-80-4 ]
[ 23978-55-4 ]
1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodo-hexane; compound with 1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecane [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 5535 - 5550

38
[ 101327-87-1 ]
[ 23978-55-4 ]
7,16-bis(8-nitro-7-quinolinylmethyl)diaza-18-crown-6 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 5h;

Reference： [1]Xue, Guoping; Bradshaw, Jerald S; Dalley, N.Kent; Savage, Paul B; Krakowiak, Krzysztof E; Izatt, Reed M; Prodi, Luca; Montalti, Marco; Zaccheroni, Nelsi [Tetrahedron, 2001, vol. 57, # 36, p. 7623 - 7628]

39
[ 23978-55-4 ]
[ 158753-17-4 ]
7,16-bis(8-amino-7-quinolinylmethyl)diaza-18-crown-6 [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 7623 - 7628

40
[ 2161-40-2 ]
[ 23978-55-4 ]
N,N'-di(tropon-2-yl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]
2-(1,4,10,13-tetraoxa-7,16-diaza-cyclooctadec-7-yl)-cyclohepta-2,4,6-trienone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 43% 2: 24%	In toluene at 100℃; for 24h;

Reference： [1]Yamamoto, Emi; Kubo, Kanji; Mori, Akira [Heterocycles, 2002, vol. 56, # 1-2, p. 305 - 311]

41
[ 38768-08-0 ]
[ 23978-55-4 ]
N,N'-di(tropon-2-yl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2003,vol. 76,p. 627 - 634

42
[ 69703-25-9 ]
[ 94605-71-7 ]
[ 23978-55-4 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 15747 - 15753

43
[ 34270-90-1 ]
[ 23978-55-4 ]
[ 142030-19-1 ]
C₂₀H₄₀N₂O₆⁽²⁺⁾*2I^(1-) [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 9553 - 9556

44
[ 4377-41-7 ]
[ 23978-55-4 ]
[ 827625-18-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In acetonitrile; at 60 - 65℃; for 9h;	16-(2-methylquinoline)-1,4,10,13-tetraoxa-7,16-diaza-cyclo-octadecane. (3a). 2-methylchloride quinoline (200 mg, 1.126 mmol) dissolved in 5 mL anhydrous acetonitrile was added dropwise to a mixture of 1,4,10,13-tetraoxa-7,16-diaza-cyclo-octadecane (354.5 mg, 1.35 mmol, 1.2 equiv.), potassium carbonate (5 equiv.) in 40 mL warm anhydrous acetonitrile in an N2 atmosphere for about an hour. The mixture was stirred at 60-65 C. for about 8 h. The solution was filtered under reduced pressure, and the filtrate was evaporated to leave a crude oil, which was purified by column chromatography on aluminium oxide with ethyl acetate:hexane=120:100 as the eluent. The product was isolated as a light yellow solid (354.4 mg, 0.88 mmol, 78%). 1H NMR (400 MHz, CDCl3): δ 8.04-8.02 (1H, d, J=8.6 Hz), 7.86-7.84 (1H, d, J=8.4 Hz), 7.65-7.63 (1H, d, J=7.6 Hz), 7.62-7.59 (1H, d, J=8.5 Hz), 7.50-7.46 (1H, t, J=6.9, 8.4 Hz), 7.32-7.29 (1H, t, J=7.0, 8.2 Hz), 4.50-4.30 (1H, br), 3.81(2H, s), 3.53-3.31 (16H, m), 2.76-2.67 (8H, m); 13C NMR (100 MHz, CDCl3): δ 161.2 (C), 147.3 (C), 136.4 (CH), 129.1 (CH), 128.7 (CH), 127.6 (CH), 127.4 (C), 125.8(CH), 121.4(CH), 70.4 (2×CH2), 70.0 (2×CH2), 69.3 (2×CH2), 69.2 (2×CH2), 61.3 (CH2), 55.1 (2×CH2), 49.0 (2×CH2); ESI-MS: m/z 404.3 (M+H)+; HRFAB-MS m/z 404.2523 (M+H)+[Calcd. for C22H34N3O4 (M+H)+ 404.2549].

Reference： [1]Organic Letters,2004,vol. 6,p. 4841 - 4844
[2]Patent: US2006/57071,2006,A1 .Location in patent: Page/Page column sheet 3/18; 11

45
[ 35231-44-8 ]
[ 23978-55-4 ]
N,N-di(7-methoxycoumarin-4-methyl)-1,10-diaza-18-crown-6 [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2005,vol. 15,p. 3084 - 3088

46
[ 23978-55-4 ]
[ 15625-89-5 ]
[ 863497-98-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	In methanol at 50℃; for 30h;

Reference： [1]Zhi, Bin Huang; Seung, Hyun Chang [Tetrahedron Letters, 2005, vol. 46, # 32, p. 5351 - 5355]

47
[ 16644-30-7 ]
[ 23978-55-4 ]
[ 883867-73-0 ]
[ 190781-92-1 ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 1050 - 1056

48
[ 23978-55-4 ]
[ 112918-82-8 ]
[ 913734-89-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 3-(9H-fluoren-9-ylmethoxycarbonylamino)pentanedioic acid With thionyl chloride for 0.5h; Heating; Stage #2: 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane With N-ethyl-N,N-diisopropylamine In dichloromethane for 7h; Further stages.;

Reference： [1]Wanichecheva, Nantanit; Benco, John S.; Lambert, Christopher R.; McGimpsey, W. Grant [Photochemistry and Photobiology, 2006, vol. 82, # 1, p. 268 - 273]

49
[ 31255-10-4 ]
[ 23978-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 79 percent / tetrabutylammonium iodide, sodium hydroxide (50 percent) / toluene; H₂O / 9 h / Heating 2: 94 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 3 steps 1: 96 percent / sodium carbonate / H₂O / 4 h / Heating 2: 79 percent / tetrabutylammonium iodide, sodium hydroxide (50 percent) / toluene; H₂O / 9 h / Heating 3: 94 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 3 steps 1: 96 percent / sodium carbonate / H₂O / 4 h / Heating 2: 94 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating

	Multi-step reaction with 3 steps 1: 96 percent / sodium carbonate / H₂O / 4 h / Heating 2: 94 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 3 steps 1: 96 percent / sodium carbonate / H₂O / 4 h / Heating 2: tetrabutylammonium iodide, sodium hydroxide (50 percent) / toluene; H₂O / 9 h / Heating 3: 94 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 2 steps 1: 79 percent / Bu₄NI, 50 percent aq. NaOH / toluene / 10 h / Heating 2: 94 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 3 steps 1: 1.) sat. aq. Na₂CO₃ / 1.) 2 h, heated, 2.) 4 h, reflux 2: 79 percent / Bu₄NI, 50 percent aq. NaOH / toluene / 10 h / Heating 3: 94 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 3 steps 1: 1.) sat. aq. Na₂CO₃ / 1.) 2 h, heated, 2.) 4 h, reflux 2: Bu₄NI, 50 percent aq. NaOH / toluene / Heating 3: 94 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 3 steps 1: 1.) sat. aq. Na₂CO₃ / 1.) 2 h, heated, 2.) 4 h, reflux 2: 50 percent aq. NaOH / toluene / reactions with var. alkylating agents in concentrated and diluted alkaline solutions 3: 94 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 3 steps 1: 1.) sat. aq. Na₂CO₃ / 1.) 2 h, heated, 2.) 4 h, reflux 2: Bu₄NI, 50 percent aq. NaOH / toluene / Heating 3: 94 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 2 steps 1: 80 percent / aq. NaOH / tetra-n-butylammonium iodide / toluene / 10 h / Heating 2: 63 percent / 45percent HBr/glacial CH₃COOH, phenol / 6 h / 40 °C

Reference： [1]Luk'yanenko, N.G.; Basok, S.S.; Filonova, L.K. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742]
[2]Luk'yanenko, N.G.; Basok, S.S.; Filonova, L.K. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742]
[3]Luk'yanenko, N.G.; Basok, S.S.; Filonova, L.K. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742]
[4]Luk'yanenko, N.G.; Basok, S.S.; Filonova, L.K. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742]
[5]Luk'yanenko, N.G.; Basok, S.S.; Filonova, L.K. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742]
[6]Lukyanenko, Nikolai G.; Basok, Stepan S.; Filonova, Lyubov K. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 3141 - 3148]
[7]Lukyanenko, Nikolai G.; Basok, Stepan S.; Filonova, Lyubov K. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 3141 - 3148]
[8]Lukyanenko, Nikolai G.; Basok, Stepan S.; Filonova, Lyubov K. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 3141 - 3148]
[9]Lukyanenko, Nikolai G.; Basok, Stepan S.; Filonova, Lyubov K. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 3141 - 3148]
[10]Lukyanenko, Nikolai G.; Basok, Stepan S.; Filonova, Lyubov K. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 3141 - 3148]
[11]Bogatsky, A. V.; Lukyanenko, N. G.; Basok, S. S.; Ostrovskaya, L. K. [Synthesis, 1984, # 2, p. 138]

50
[ 36839-55-1 ]
[ 23978-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / lithium aluminum hydride / tetrahydrofuran / 20 h / Heating
	Multi-step reaction with 2 steps 1: 29 percent / Na₂CO₃ / acetonitrile / 30 h / Heating 2: 92 percent / H₂ / 10percent Pd/C / ethanol / 24 h / 25 °C / 3102.9 Torr
	Multi-step reaction with 2 steps 1: Bu₄NI, 50 percent aq. NaOH / toluene / Heating 2: 94 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating

	Multi-step reaction with 2 steps 1: 68 percent / Na₂CO₃, NaI / acetonitrile / Heating 2: H₂
	Multi-step reaction with 2 steps 1: 29 percent / Na₂CO₃ / acetonitrile / 24 h / Heating 2: H₂

Reference： [1]Luk'yanenko, N.G.; Basok, S.S.; Filonova, L.K. [Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571][Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742]
[2]Gatto, Vincent J.; Gokel, George W. [Journal of the American Chemical Society, 1984, vol. 106, # 26, p. 8240 - 8244]
[3]Lukyanenko, Nikolai G.; Basok, Stepan S.; Filonova, Lyubov K. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 3141 - 3148]
[4]Gatto, Vincent J.; Arnold, Kristin A.; Viscariello, Anthony M.; Miller, Steven R.; Gokel, George W. [Tetrahedron Letters, 1986, vol. 27, # 3, p. 327 - 330]
[5]Gatto, Vincent J.; Arnold, Kristin A.; Viscariello, Anthony M.; Miller, Steven R.; Gokel, George W. [Tetrahedron Letters, 1986, vol. 27, # 3, p. 327 - 330]

51
[ 23978-55-4 ]
[ 31255-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76 percent / Et₃N / CHCl₃; diethyl ether / Ambient temperature 2: 91 percent / LiAlH₄ / diethyl ether / Heating

Reference： [1]Jong, F. de; Zon, A. van; Reinhoudt, D. N.; Torny, G. J.; Tomassen, H. P. M. [Recueil des Travaux Chimiques des Pays-Bas, 1983, vol. 102, # 3, p. 164 - 173]

52
[ 23978-55-4 ]
[ 69703-25-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 78 percent / pyridine / CH₂Cl₂ / 2 h / 25 °C 2: 91 percent / BH₃ / tetrahydrofuran / 2 h / Heating

Reference： [1]Keana, John F. W.; Cuomo, John; Lex, Laszlo; Seyedrezai, Seyed E. [Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2647 - 2654]

53
[ 23978-55-4 ]
[ 54761-04-5 ]
Yb⁽³⁺⁾*C₁₂H₂₆O₄N₂*3CF₃SO₃^(1-)={Yb(C₁₂H₂₆O₄N₂)}(CF₃SO₃)3 [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1989,p. 367 - 370

54
[ 16265-04-6 ]
[ 23978-55-4 ]
[ 1214885-21-8 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1160 - 1163

55
[ 50-00-0 ]
[ 7545-59-7 ]
[ 23978-55-4 ]
[ 1245934-90-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	In 1,4-dioxane for 3h; Inert atmosphere; Microwave irradiation;

Reference： [1]Location in patent: experimental part Farruggia, Giovanna; Iotti, Stefano; Lombardo, Marco; Marraccini, Chiara; Petruzziello, Diego; Prodi, Luca; Sgarzi, Massimo; Trombini, Claudio; Zaccheroni, Nelsi [Journal of Organic Chemistry, 2010, vol. 75, # 18, p. 6275 - 6278]

56
[ 19835-38-2 ]
[ 23978-55-4 ]
[ 1258781-64-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	With triethylamine; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere;	General procedure: Method b: In a reaction vessel under a stream of N2, one equivalent of diaza-18-crown-6 was dissolved in THF, and 2.5 equivalents of triethylamine were added. The resulting mixture was stirred at ambient temperature for 10 min, and a solution of corresponding acyl chloride (two equivalents) was added. The reaction mixture was stirred at ambient temperature for additional 24 h, filtered and the filtrate was evaporated under reduced pressure. The solid residue was suspended in CH2Cl2, washed with saturated solution of NaCl and dried over anhydrous MgSO4. After removal of the solvent, under reduced pressure, the oily product was obtained. The product is additionally purified by column chromatography.
56%	With triethylamine; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere;	Method b) In a reaction vessel under a stream of inert gas, N2 or Ar, one equivalent of corresponding aza-18-crown-6 was dissolved or suspended in the appropriate anhydrous solvent comprising the following: THF, glyme, diglyme, or DMF, DMSO and particularly THF, and minimally 2.5 equivalents of base (triethylamine or pyridine) was added. The resulting mixture was stirred at room temperature for 10 min and a solution or suspension of corresponding acyl chloride (one or two equivalents) was added. The reaction mixture was stirred at room temperature for additional 24 hours, filtered and the filtrate was evaporated under reduced pressure. The solid residue was suspended in appropriate solvent (CH2Cl2, glyme or diglyme, preferably CH2Cl2), washed with saturated solution of NaCl and dried over anhydrous MgSO4 or Na2SO4. After removal of the solvent under reduced pressure, oily product was obtained. When needed, the product was additionally purified by column chromatography. By following the general procedure, (Method b) the compound was obtained via reaction of diaza-18-crown-6 (0.68g, 0.0026 mol) with l-(chloroethanoyl)adamantane(1.10 g, 0.0052 mol). The crude product was purified via column chromatography onAl2O3 (act. II-III) using 0→2 % MeOH in CH2Cl2 as an eluent, thereby yielding 0.861 g (56 %) of colourless oily product. Analytically a pure sample was obtained by chromatography on a small column of Al2O3 (act. II-III) using 0- »2 % MeOH inCH2Cl2 as an eluent.IR (KBr) v/cnT1 : 2905 (s), 2845 (s), 1449 (m), 1351 (m), 1126 (s).1H NMR (CDCl3) δ/ppm: 1.62 - 1.72 (m, 24 H), 1.97 (br. s, 6H), 2.12 (s, 4H), 3.50 -3.70 (m, 24 H).13C NMR (CDCl3) δ/ppm: 28.38 (d, 6C), 33.37 (s, 2C), 36.54 (t, 6C), 42.42 (t, 6C),45.48 (t, 1C), 45.56 (t, 1C), 46.33 (t, 1C), 46.57 (t, 1C), 48.97 (t, 1C), 49.18 (t,1C),68.97 (t, 1C), 69.63 (t, 1C), 69.81 (t, 1C), 70.08 (t, 1C), 70.22 (t, 1C), 70.39 (t,1C), 70.44 (t, 1C), 70.59 (t, 1C), 171.17 (s, 1C), 171.24 (s, 1C).Anal, calcd for C36H58N2O6 ( Mr=614.856): C 70.32; H 9.51; N 4.65. Found C 69.99;H 9.26; N 4.64.HRMS calculated for [C36H58N2O6 + H] 615.4368. Found 615. 4379.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3444 - 3454
[2]Patent: WO2010/146404,2010,A1 .Location in patent: Page/Page column 19
[3]Croatica Chemica Acta,2012,vol. 85,p. 559 - 568
[4]Molecules,2021,vol. 26

57
[ 26831-48-1 ]
[ 23978-55-4 ]
[ 1258781-62-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium carbonate; In acetonitrile; at 80℃; for 120h;Inert atmosphere;	General procedure: Method a: In a reaction vessel under a stream of N2, two equivalents of corresponding tosylate and one equivalent of diaza-18-crown-6 were dissolved in acetonitrile. To the stirred solution, four equivalents of Na2CO3 were added. The reaction mixture was heated at 80 C, for five days, after which the reaction mixture was cooled to the ambient temperature and concentrated in vacuo. The solid residue was suspended in CH2Cl2, and filtered through a plug of celite. The combined filtrates were concentrated under reduced pressure to afford oily product. If needed, product was additionally purified by column chromatography.
54%	With sodium carbonate; In acetonitrile;Inert atmosphere; Heating;	Method a) In a reaction vessel under a stream of inert gas, N2 or Ar, one or two equivalents of corresponding tosylate and one equivalent of corresponding aza-18- crown-6 were dissolved or suspended in the appropriate anhydrous solvent: acetonitrile, THF, DME, glyme, diglyme, or DMF, DMSO and particularly acetonitrile. To the stirred reaction mixture minimally four equivalents of base were added. The bases used herein comprise Na2CO3, K2CO3, CsCO3 and preferably Na2CO3. The reaction mixture was heated at elevated temperature, preferably at 80 C, for two to five days, after which the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The solid residue was suspended in appropriate solvent CH2Cl2, glyme or diglyme, preferably CH2Cl2, and filtered through a plug of celite. The combined filtrates were concentrated under reduced pressure to yield oily product. If needed, the product was additionally purified by column chromatography. By following the general procedure (Method a) the product was obtained via reaction of l-(2-tosyloxyethyl)adamantane (0.668 g, 0.002 mol) and diaza-18-crown-6 (0.262 g, 0.001 mol). The crude product was purified via column chromatography on Al2O3 (act. II-III) using 0→2 % MeOH in CH2Cl2 as an eluent thereby yielding 0.317 g (54%) of colourless oily product. Analytically pure sample was obtained by chromatography on a small column of Al2O3 (act. II-III) using 0-»2% MeOH inCH2Cl2 as an eluent.IR (KBr) v/crn 1 : 2903 (s), 2852 (s), 1628 (s), 1462 (m), 1133 (m), 1110 (m), 1096(m).1H NMR (CDCl3) δ/ppm : 1.20 - 1.30 (m, 4H), 1.47 (br. s, 12H), 1.55 - 1.75 (m,12H), 1.92 (br. s, 6H), 2.45 - 2.60 (m, 4H), 2.70 - 2.85 (m, 8H), 3.55 - 3.70 (m,16H).13C NMR (CDCl3) δ/ppm : 28.55 (d, 6C), 31.65 (s, 2C), 37.07 (t, 6C), 40.69 (t, 2C),42.43 (t, 6C), 49.66 (t, 2C), 53.75 (t, 4C), 69.80 (t, 4C), 70.60 (t, 4C).HRMS calculated for [C36H62N2O4 + H]587.4782. Found 587.4758.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3444 - 3454
[2]Patent: WO2010/146404,2010,A1 .Location in patent: Page/Page column 17-18
[3]Croatica Chemica Acta,2012,vol. 85,p. 559 - 568

58
[ 3405-88-7 ]
[ 23978-55-4 ]
2C₈H₇ClO₂S*C₁₂H₂₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In methanol at 20℃; for 12h;

Reference： [1]Location in patent: experimental part Adamovich; Mirskova; Mirskov; Perminova; Chipanina; Aksamentova; Voronkov [Russian Journal of General Chemistry, 2010, vol. 80, # 5, p. 1007 - 1010]

59
[ 23978-55-4 ]
[ 118-97-8 ]
[ 111622-73-2 ]

Reference： [1]Revue Roumaine de Chimie,2009,vol. 54,p. 889 - 894

60
[ 2094-72-6 ]
[ 23978-55-4 ]
[ 148515-35-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere;	General procedure: Method b: In a reaction vessel under a stream of N2, one equivalent of diaza-18-crown-6 was dissolved in THF, and 2.5 equivalents of triethylamine were added. The resulting mixture was stirred at ambient temperature for 10 min, and a solution of corresponding acyl chloride (two equivalents) was added. The reaction mixture was stirred at ambient temperature for additional 24 h, filtered and the filtrate was evaporated under reduced pressure. The solid residue was suspended in CH2Cl2, washed with saturated solution of NaCl and dried over anhydrous MgSO4. After removal of the solvent, under reduced pressure, the oily product was obtained. The product is additionally purified by column chromatography.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3444 - 3454
[2]Croatica Chemica Acta,2012,vol. 85,p. 559 - 568
[3]Molecules,2021,vol. 26

61
[ 24424-99-5 ]
[ 23978-55-4 ]
N,N'-di-tert-butoxycarbonyl-4,13-diaza-18-crown-6 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		For the N-boc protection of amines, to solution of diboc (1 mmol) in ethanol (5 ml) was added {K18-crown-6]Br3}n (0.001 mmol). The solution was stirred at room temperature for 1 min. The amine (1 mmol) was then added and solution as stirred at room temperature for an appropriate time (table 1). After completion of the reaction, the solvent was removed by water bath distillation. To the residue was added ethyl acetate (5 ml) and the mixture was filtered (the catalyst is insoluble in n-hexane and ethyl acetate). The solid was washed with ethyl acetate ()10 ml2) amd combined filtrates were reduced to dryness to yield the pure products.

Reference： [1]Cuihua Xuebao/Chinese Journal of Catalysis,2013,vol. 34,p. 1730 - 1733
[2]Journal of the Chinese Chemical Society,2011,vol. 58,p. 538 - 543

62
[ 1493-27-2 ]
[ 23978-55-4 ]
C₂₄H₃₂N₄O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 6h;Inert atmosphere;	(1,4,10,13)-Tetraoxa-7,16-diazacyclooctadecane (206 mg, 0.785 mmol), o-fluoronitrobenzene (175 lL, 1.65 mmol) and triethylamine (241 lL, 1.73 mmol) were dissolved in 2.5 mL of anhydrous DMF. The yellow solution was stirred for 6 h at 100 oC. The rsulting orange solution is concentrated under vacuum and diluted with dichloromethane and washed with aquous solution of NaHCO3, water, then saturated solution of NaCl. The organic phasewas dried on anhydrous Na2SO4, filtered then evaporated to dryness to give 1 yellow crystalline solid (696 mg, 90%). 1H NMR (250 MHz, CDCl3): d 7.65 (dd, 3JHH = 8.1 Hz, 4JHH = 1.2 Hz,2H), 7.31-7.51 (m, 4H), 6.93-7.04 (m, 2H), 3.61 (t, 3JHH = 5.3 Hz,8H, OCH2CH2N), 3.55 (s, 8H, OCH2CH2O), 3.47 (t, 3JHH = 5.3 Hz,8H, OCH2CH2N). 13C NMR (62.5 MHz, CDCl3): d 145.1 (CAr-NO2),136.6 (CAr-Nethercrown), 125.4, 123.4, 117.7 and 115.2 (CAr-H),70.5, 54.7 and 69.0 (CH2O and CH2N). Elemental Anal. Calc. for C24H32N4O8: C, 57.13; H, 6.39; N, 11.10. Found: C, 56.77; H, 6.54;N, 11.48%.

Reference： [1]Polyhedron,2014,vol. 68,p. 191 - 198

63
[ 83004-10-8 ]
[ 23978-55-4 ]
7,16-bis[(6-bromopyridin-2-yl)methyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; potassium iodide; In acetonitrile;Reflux;	General procedure: A one-neck flask equipped with a magnetic stirrer and reflux condenser was charged with diazacrown ether (0.86-2.3 mmol), aryl halide halogenomethyl derivative (1.7-4.6 mmol), dry acetonitrile (3-8 mL) and sodium or potassium carbonate (3.4-11.2 mmol). The reaction mixture was stirred under reflux for several hours, the residue was filtered off, washed with CH2Cl2, and the combined organic fractions were evaporated in vacuo, dissolved in CH2Cl2 (5-20 mL), washed three times with equal volumes of distilled water, dried over 4 A molecular sieves, and the CH2Cl2 was evaporated in vacuo to give the pure target product. We have previously reported the synthesis and spectral data of compounds 6-9 [15].

Reference： [1]Molecules,2014,vol. 19,p. 940 - 965

64
[ 83004-10-8 ]
[ 23978-55-4 ]
11,14,27,30,35,38-hexaoxa-1,8,17,24,41,42-hexaazatetracyclo[22.8.8.1^3,7.1^18,22]dotetraconta-3⁽⁴²⁾,4,6,18⁽⁴¹⁾,19,21-hexaene [ No CAS ]

Reference： [1]Molecules,2014,vol. 19,p. 940 - 965

65
[ 598-21-0 ]
[ 23978-55-4 ]
1,1'-(1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-7,16-diyl)bis(2-bromoethanone) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		Under Ar gas protection, compound 9 (0.2 g, 0.76 mmol) was dissolved in 10 mL dry CH2Cl2. Sodium hydride(73 mg, 3.05 mmol) was added slowly and stirred for 15 min at room temperature, then bromoacetyl bromide (0.17 mL in 7 mL dry CH2Cl2) was added dropwise to the flask and stirred for another 6 h at room temperature (Scheme 2). The reaction solution was concentrated in vacuum and chromatographed on a column of silica (silica gel, 20% methanol/CH2Cl2) to obtain 0.28 g (73%) compound 8 as a colorless liquid. 1H NMR (400 MHz, CDCl3): δ 3.96 (d, 4H, J = 3.1 Hz), 3.75 (d, 4H, J = 5.3 Hz), 3.71-3.56 (m, 20H). 13C NMR (100 MHz, CDCl3): δ 170.44, 168.71, 70.95, 70.81, 70.70, 70.45, 69.82, 69.54, 69.17, 69.10, 50.53, 50.50, 48.54. MS (EI): m/z Calcd. for C16H28Br2N2O6 [M]+: 504.2. Found:504.2.

Reference： [1]Chinese Chemical Letters,2015,vol. 26,p. 851 - 856
[2]Organic and Biomolecular Chemistry,2021,vol. 19,p. 146 - 150

66
[ 67852-88-4 ]
[ 23978-55-4 ]
PhCH₂OCO(CH₂)8CON₁₈NCO(CH₂)8CO₂CH₂Ph [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		General procedure: A mixture of octanedioic acid monobenzyl ester (1.87 g, 7.09mmol), HBTU (2.70 g, 7.12 mmol), and DIPEA (7.31 mL, 42.0mmol) in CH2Cl2 (50 mL) was stirred at r.t. for 10 min. Diaza-18-crown-6 (2; 0.837 g, 3.19 mmol) was added in one portion and the mixture was allowed to stir at r.t. for 18 h. The reaction mixture was washed with H2O (3 × 50 mL) and dried (MgSO4); chromatography (silica gel; MeOH-CHCl3, 0:100 to 10:90) afforded a yellow oil; yield: 2.22 g (92%).
90%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine;	[0107] PhCH2OCO(CH2)8C0 CO(CH2)8CO2CH2Ph. This compound was prepared similarly to PhCH2OCO(CH2)6C0CO(CH2)6CO2CH2Ph. Decanedioic acid monobenzyl ester (2.23 g, 7.62 mmol), HBTU (2.89 g, 7.62 mmol), Et(i-Pr)2N (7.85 mL, 45.1 mmol), and diaza-18-crown-6 (0.900 g, 3.43 mmol) afforded a colorless oil (2.50 g, 90%). 1H-NMR: 0.99 (16H, bs), 1.31 (8H, bs), 2.03 (8H, m), 3.18-3.36 (24H, m), 6.89-7.07 (1OH, m). 13C-NMR: 24.11, 24.49, 28.22, 28.32, 28.50, 28.53, 32.19, 33.33, 37.73, 46.21, 46.29, 48.03, 48.11, 65.02,68.94, 69.07, 69.32, 69.63, 69.77, 69.91, 70.04, 127.27, 127.69, 135.49, 172.25, 172.27, 172.39.

Reference： [1]Synthesis,2014,vol. 46,p. 2771 - 2779
[2]Patent: WO2016/22991,2016,A1 .Location in patent: Paragraph 0107

67
[ 88353-04-2 ]
[ 23978-55-4 ]
[ 1007834-20-9 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: A mixture of octanedioic acid monobenzyl ester (1.87 g, 7.09mmol), HBTU (2.70 g, 7.12 mmol), and DIPEA (7.31 mL, 42.0mmol) in CH2Cl2 (50 mL) was stirred at r.t. for 10 min. Diaza-18-crown-6 (2; 0.837 g, 3.19 mmol) was added in one portion and the mixture was allowed to stir at r.t. for 18 h. The reaction mixture was washed with H2O (3 × 50 mL) and dried (MgSO4); chromatography (silica gel; MeOH-CHCl3, 0:100 to 10:90) afforded a yellow oil; yield: 2.22 g (92%).

Reference： [1]Synthesis,2014,vol. 46,p. 2771 - 2779

68
[ 88353-04-2 ]
[ 23978-55-4 ]
[ 1007834-21-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 18 h / 20 °C / Inert atmosphere

Reference： [1]Curvey, Nichole S.; Luderer, Sarah E.; Walker, John K.; Gokel, George W. [Synthesis, 2014, vol. 46, # 20, p. 2771 - 2779]

69
14-(benzyloxy)-14-oxotetradecanoic acid [ No CAS ]
[ 23978-55-4 ]
C₅₄H₈₆N₂O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: A mixture of octanedioic acid monobenzyl ester (1.87 g, 7.09mmol), HBTU (2.70 g, 7.12 mmol), and DIPEA (7.31 mL, 42.0mmol) in CH2Cl2 (50 mL) was stirred at r.t. for 10 min. Diaza-18-crown-6 (2; 0.837 g, 3.19 mmol) was added in one portion and the mixture was allowed to stir at r.t. for 18 h. The reaction mixture was washed with H2O (3 × 50 mL) and dried (MgSO4); chromatography (silica gel; MeOH-CHCl3, 0:100 to 10:90) afforded a yellow oil; yield: 2.22 g (92%).

Reference： [1]Synthesis,2014,vol. 46,p. 2771 - 2779

70
[ 146004-98-0 ]
[ 23978-55-4 ]
C₅₈H₉₄N₂O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: A mixture of octanedioic acid monobenzyl ester (1.87 g, 7.09mmol), HBTU (2.70 g, 7.12 mmol), and DIPEA (7.31 mL, 42.0mmol) in CH2Cl2 (50 mL) was stirred at r.t. for 10 min. Diaza-18-crown-6 (2; 0.837 g, 3.19 mmol) was added in one portion and the mixture was allowed to stir at r.t. for 18 h. The reaction mixture was washed with H2O (3 × 50 mL) and dried (MgSO4); chromatography (silica gel; MeOH-CHCl3, 0:100 to 10:90) afforded a yellow oil; yield: 2.22 g (92%).

Reference： [1]Synthesis,2014,vol. 46,p. 2771 - 2779

71
[ 146004-98-0 ]
[ 23978-55-4 ]
C₄₄H₈₂N₂O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 18 h / 20 °C / Inert atmosphere

Reference： [1]Curvey, Nichole S.; Luderer, Sarah E.; Walker, John K.; Gokel, George W. [Synthesis, 2014, vol. 46, # 20, p. 2771 - 2779]

72
[ 100-52-7 ]
[ 23978-55-4 ]
[ 69703-25-9 ]
[ 94605-71-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 65%	With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; Inert atmosphere;	N-Benzyl-4,13-diaza-18-crown-6 (3) A mixture of 4,13-diaza-18-crown-6 (2; 2.76 g, 10.51 mmol), NaBH(OAc)3 (1.67 g, 7.88 mmol), benzaldehyde (0.54 mL, 5.3mmol), and CH2Cl2 (135 mL) was stirred overnight at r.t. and then quenched with MeOH (3 mL) and dried (MgSO4). The off-white residue was mixed with Et2O (100 mL) and filtered, after which it was chromatographed (dry loaded, silica gel, NH4OH-MeOH-CH2Cl2, 0.5:2:97.5 to 0.5:5:94.5). Dibenzyl crown 4 eluted first and was obtained as an off-white solid; yield: 0.70 g (30%). Monobenzyl diazacrown 3 eluted next and was obtained as a yellow oil; yield:1.21 g (65%).

Reference： [1]Curvey, Nichole S.; Luderer, Sarah E.; Walker, John K.; Gokel, George W. [Synthesis, 2014, vol. 46, # 20, p. 2771 - 2779]

73
[ 15570-39-5 ]
[ 23978-55-4 ]
C₄₂H₆₂N₂O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		A mixture of octanedioic acid monobenzyl ester (1.87 g, 7.09mmol), HBTU (2.70 g, 7.12 mmol), and DIPEA (7.31 mL, 42.0mmol) in CH2Cl2 (50 mL) was stirred at r.t. for 10 min. Diaza-18-crown-6 (2; 0.837 g, 3.19 mmol) was added in one portion and the mixture was allowed to stir at r.t. for 18 h. The reaction mixture was washed with H2O (3 × 50 mL) and dried (MgSO4); chromatography (silica gel; MeOH-CHCl3, 0:100 to 10:90) afforded a yellow oil; yield: 2.22 g (92%).

Reference： [1]Synthesis,2014,vol. 46,p. 2771 - 2779

74
[ 56908-88-4 ]
[ 23978-55-4 ]
7,16-bis(3,5-dibromobenzyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium carbonate; In acetonitrile; for 8h;Reflux;	A oneneckedflask equipped with a magnetic stirrer and reflux condenser was charge with diaza-18-crown-6 ether (12) (1.5 mmol, 393 mg), <strong>[56908-88-4]3,5-dibromobenzyl bromide</strong> (13) (3 mmol, 987 mg), 7.5ml dry MeCN was added followed by finely powdered sodium carbonate (7.5 mmol, 795 mg).The reaction was refluxed for 8 h, after cooling down to room temperature the residue wasfiltered off, washed with 5 ml dichloromethane, combined organic fractions were evaporated invacuo, the residue was dissolved in 5 ml dichloromethane, washed by water (3x5 ml), dried over molecular sieves 4A, the solvent was evaporated in vacuo to produce target compound as ayellow-greenish oil. Yield 1117 mg (99%).

Reference： [1]Letters in Organic Chemistry,2018,vol. 15,p. 425 - 430

75
[ 23978-55-4 ]
[ 117330-41-3 ]
[ 117441-50-6 ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium carbonate In acetonitrile for 34h; Inert atmosphere; Reflux;	2 2.2. Synthesis of iron cryptate 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane (90 mg) was dissolvedin CH3CN (200 mL) under a nitrogen atmosphere. Next, Na2CO3(363 mg) was added. The resulting suspension was heated to reflux, and in CH3CN (250 mL) was added under high dilution conditions over16 h. The mixture was then heated under reflux for an additional 18 h. After cooling to ambient temperature, the product was concentrated under reduced pressure and was subjected to column chromatography(SiO2, gradient: CH2Cl2/MeOH, 100:1→25:1) to yield compound 3(see Scheme 1), a colorless solid (29%). 200 mg of compound 3 and40 mg of potassium carbonate were dissolved in 40 mL of CH3OH and20 mL of H2O. The solution was heated to 70 °C under reflux for 3 h.After cooling, HCl was added to neutralise the solution. After further treatment with diethyl ether, compound 4 was precipitated. 50 mg of compound 4 and 40 mg of Fe(ClO4)3 were then dissolved in a mixture of CH3CN and 20 mL of H2O, and left to react for 2 days. The solvent was then filtered and treated with diethyl ether. The final product was precipitated and vacuum dried.

Reference： [1]Lan, Lintao; Liu, Yuanzhong; Chen, Xifeng; Zhang, Tian; Dong, Ningning; Miao, Peng [Electrochemistry Communications, 2019, vol. 98, p. 92 - 95]

76
[ 14649-03-7 ]
[ 23978-55-4 ]
threo-N₇,N₁₆-bis((S)-1-phenylethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-7,16-dicarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In diethyl ether; chloroform at 0℃; for 24h;	Compound 1 To a solution of 2.54 g (9.68 mmol) 1,10-diaza-18-crown-6 (Pilot Plant, Physicochemical Institute, Academy of Sciences of Ukraine) in 30 ml of anhydrous chlorophorm at 0 °C a solution of 2.85 g (19.4 mmol) of S-α-phenylethylisocyanate in 20 ml of dry diethyl ether (DEE) cooled to 0 °C was added. In 24 h the solvent was distilled to dryness. The residue was washed with DEE (15 ml×3) and crystallized from a 1:5 ethanol-DEE mixture. Yield 4.79 g (89%); mp 126-127 °C. After the second crystallization from isopropanol m. p. was 133 °C (at a point). 1H NMR. CDCl3. 1.42-1.43, d, J = 6.59, 6H (Me); 3.41-3.64, m, 24H (CE); 4.88, q, J = 6.59, 2H (CH); 6.23-6.24, d, J = 5.76, 2H (NH); 7.19, t, J = 6.86, 2H (-Ph) 7.30, m, 8H (o-, m-Ph). 13C NMR. CDCl3 23.24, 2C; 50.21, 2C; 50.38, 4C; 70.71, 4C; 71.48, 4C; 126.07, 4C; 126.76, 2C; 128.39, 4C; 145.17, 2C; 158.74, 2C. Mass: m/z (%): 556 ([M]+, 2); 437([M-MePhCHN]+, 3); 409 ([M-MePhCHNHCO]+, 12); 263 ([HN(C2H4OC2H4OC2H4)2NH2]+, 19); 132 ([(C2H4O)3]+, 100); 120 ([MePhCHNH]+, 18); 105 ([MePhCH]+26), 77 ([Ph]+, 8). Calculated for C30H44N4O6 (%): C 64.73, H 7.97, N 10.06. Found C 64.69, H 8.01, N 10.04; [α]20D= +18.952 (with 2.1 CHCl3).

Reference： [1]Fonari; Pluzhnik-Gladyr; Kamalov; Kravtsov, V. Kh. [Journal of Structural Chemistry, 2019, vol. 60, # 1, p. 143 - 150][Zh. Strukt. Kim., 2019, vol. 60, # 1, p. 150 - 157,8]

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CAS No. :	23978-55-4	MDL No. :	MFCD00005112
Formula :	C₁₂H₂₆N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NLMDJJTUQPXZFG-UHFFFAOYSA-N
M.W :	262.35	Pubchem ID :	72805
Synonyms :

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:

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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 23978-55-4 ] Synthesis Path-Downstream 1~76

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