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Product Details of [ 295-37-4 ]

CAS No. :295-37-4 MDL No. :MFCD00005105
Formula : C10H24N4 Boiling Point : -
Linear Structure Formula :(NHCH2CH2NHCH2CH2CH2)2 InChI Key :MDAXKAUIABOHTD-UHFFFAOYSA-N
M.W : 200.32 Pubchem ID :64964
Synonyms :
Chemical Name :1,4,8,11-Tetraazacyclotetradecane

Safety of [ 295-37-4 ]

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 [ 295-37-4 ]

* 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.

  • Upstream synthesis route of [ 295-37-4 ]
  • Downstream synthetic route of [ 295-37-4 ]

[ 295-37-4 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 71089-74-2 ]
  • [ 295-37-4 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at 100℃; for 48 h;
Stage #2: With sodium hydroxide In water
1,4,8,11-Tetra-p-tosyl-1,4,8,11-tetraazacyclotetradecane (13 mmol) was dissolved in 90percent concentrated sulfuric acid, allowed to react with stir at 100°C for 48 hours, and cooled to 0°C. To the resultant was dropwise added anhydrous ethanol (120 ml) and anhydrous ethyl ether (100 ml) successively. A solid was precipitated and filtrated. The filter cake was washed with a small amount of anhydrous ethanol and anhydrous ethyl ether, dried in vacuum. The resultant off white solid was dissolved with NaOH aqueous solution (90 ml, 1 mol/L), and extracted with chloroform (3x100 ml). The chloroform layer was dried over anhydrous sodium sulfate over night, reduced pressure distilled off chloroform, dried in vacuum to give a white solid product, recrystallized with toluene to obtain 2.2 g of 1,4,8,11-tetraazacyclotetradecane, yield 85percent, MS[M]+=200.3 m/e, 1H-NMP(400 M HZ, CDCl3)δppm: 1.72(t, 4H), 2.23 (s, 4H), 2.68 (s, 8H), 2.75 (t, 8H).
Reference: [1] Patent: EP2163553, 2010, A1, . Location in patent: Page/Page column 18-19
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 2, p. 372 - 376[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 2, p. 413 - 417
[4] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 3, p. 346 - 349[5] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 3, p. 401 - 404
[6] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571[7] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742
[8] Canadian Journal of Chemistry, 1995, vol. 73, # 5, p. 685 - 695
  • 2
  • [ 596820-95-0 ]
  • [ 295-37-4 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 25, p. 4573 - 4579
  • 3
  • [ 74676-47-4 ]
  • [ 295-37-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571[2] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 3, p. 346 - 349[4] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 3, p. 401 - 404
  • 4
  • [ 4741-99-5 ]
  • [ 295-37-4 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 21, p. 3271 - 3282
[2] Synthetic Communications, 2006, vol. 36, # 21, p. 3271 - 3282
[3] Synthetic Communications, 2006, vol. 36, # 21, p. 3271 - 3282
[4] Tetrahedron, 2003, vol. 59, # 25, p. 4573 - 4579
[5] Tetrahedron, 2003, vol. 59, # 25, p. 4573 - 4579
[6] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 2, p. 372 - 376[7] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 2, p. 413 - 417
  • 5
  • [ 96455-17-3 ]
  • [ 295-37-4 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 38, p. 5505 - 5508
  • 6
  • [ 596820-91-6 ]
  • [ 295-37-4 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 25, p. 4573 - 4579
[2] Tetrahedron, 2003, vol. 59, # 25, p. 4573 - 4579
  • 7
  • [ 144534-68-9 ]
  • [ 295-37-4 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 38, p. 5505 - 5508
  • 8
  • [ 10563-26-5 ]
  • [ 295-37-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1562 - 1571[2] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 8, p. 1731 - 1742
  • 9
  • [ 111514-29-5 ]
  • [ 295-37-4 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 2, p. 372 - 376[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 2, p. 413 - 417
  • 10
  • [ 917838-66-5 ]
  • [ 295-37-4 ]
  • [ 1571-33-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 2006, vol. 71, # 3, p. 337 - 367
  • 11
  • [ 4741-99-5 ]
  • [ 109-64-8 ]
  • [ 295-37-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1937, vol. 56, p. 343,347
[2] Inorg. Chem., 1963, vol. 4, p. 1102,1107
  • 12
  • [ 131543-46-9 ]
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Reference: [1] Canadian Journal of Chemistry, 1995, vol. 73, # 5, p. 685 - 695
  • 13
  • [ 131543-46-9 ]
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  • [ 295-37-4 ]
  • [ 78303-77-2 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1981, # 6, p. 302 - 304
  • 14
  • [ 64-17-5 ]
  • [ 107-15-3 ]
  • [ 109-64-8 ]
  • [ 295-37-4 ]
  • [ 4741-99-5 ]
  • [ 62708-55-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 835[2] Recueil des Travaux Chimiques des Pays-Bas, 1937, vol. 56, p. 345
  • 15
  • [ 64-17-5 ]
  • [ 107-15-3 ]
  • [ 109-64-8 ]
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  • [ 4741-99-5 ]
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 835[2] Recueil des Travaux Chimiques des Pays-Bas, 1937, vol. 56, p. 345
  • 16
  • [ 295-37-4 ]
  • [ 110078-46-1 ]
Reference: [1] New Journal of Chemistry, 2001, vol. 25, # 9, p. 1168 - 1174
[2] Tetrahedron Letters, 2003, vol. 44, # 12, p. 2481 - 2483
[3] Patent: WO2017/37639, 2017, A1,
  • 17
  • [ 623-24-5 ]
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  • [ 110078-46-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1991, # 4, p. 206 - 207
  • 18
  • [ 295-37-4 ]
  • [ 24424-99-5 ]
  • [ 170161-27-0 ]
YieldReaction ConditionsOperation in experiment
30% at 0℃; ,4,8-Tris(ter-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecane (1) was synthesized. Synthesis of 1 was performed by reported methods by Dessolin et al. (J. Dessolin, P. Galea, P. Vlieghe, J. Chermann, J. Kraus, J. Med. Chem. 1999,42, 229-241) with slight modifications. Typically, to a 1gm of cyclam (5.00 mmol, 1 equiv. ) in ice cold CH2C12 (lOOmL) was added to 2.0g of di-tert-butyl dicarbonate (9.00 mmol, 1.8 equiv. ). The solution was stirred overnight. After solvent evaporation, the crude pale yellow oil was {JND0255. DOC;1} - 34 - purified by flash column chromatography (MeOH/CH2Cl2 5: 95). The first fraction collected was the desired tri-boc protected cyclam (1) as the thick colorless oil (0.75g, 30percent yield). MS (electrospray) 523 (M+Na)+
Reference: [1] Molecular Pharmaceutics, 2017, vol. 14, # 5, p. 1395 - 1404
[2] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 21, p. 4965 - 4972
[3] Journal of the American Chemical Society, 2006, vol. 128, # 45, p. 14448 - 14449
[4] Chemical Communications, 2018, vol. 54, # 33, p. 4116 - 4119
[5] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 1, p. 65 - 73
[6] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 7, p. 1075 - 1086
[7] Chemical Communications, 2018, vol. 54, # 69, p. 9619 - 9622
[8] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 9, p. 3007 - 3010
[9] European Journal of Inorganic Chemistry, 2006, # 12, p. 2357 - 2363
[10] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 1, p. 71 - 74
[11] Patent: WO2005/117997, 2005, A1, . Location in patent: Page/Page column 34-35
[12] Nucleosides and Nucleotides, 1998, vol. 17, # 5, p. 957 - 968
[13] Tetrahedron Letters, 2002, vol. 43, # 13, p. 2463 - 2466
[14] Synlett, 2004, # 3, p. 453 - 456
[15] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 23, p. 5988 - 5992
[16] Chemical Communications, 2003, # 15, p. 1812 - 1813
[17] ChemMedChem, 2010, vol. 5, # 8, p. 1272 - 1281
[18] Patent: WO2014/153624, 2014, A1, . Location in patent: Page/Page column 42; 43; 44
[19] Biomacromolecules, 2018, vol. 19, # 2, p. 392 - 401
[20] Patent: WO2010/126888, 2010, A1, . Location in patent: Page/Page column 12; 33
  • 19
  • [ 295-37-4 ]
  • [ 24424-99-5 ]
  • [ 1007858-12-9 ]
  • [ 170161-27-0 ]
YieldReaction ConditionsOperation in experiment
35% at 0 - 20℃; Boc Cyclam. [0180] A solution of t-butyl dicarbonate (Boc2O) (2.96 g, 13.1 mmol) in 80 mL of methylene chloride (CH2Cl2) was added dropwise over a period of 2 hours to a solution of cyclam (0.88 g, 4.4 mmol) in CH2Cl2 at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated and purified by chromatography (ethyl acetate (AcOEt)→10:1 AcOEt:methanol (CH3OH)) to give cyclam-Boc4 (0.91 g, 35percent) as a white set foam and cyclam-Boc3 (1.22 g, 56percent) as a light yellow set foam. Tri Boc cyclam: 1H NMR (CDCl3) δ 1.46 (s, 27H), 1.65-1.76 (m, 2H), 2.00-1.80 (m, 2H), 2.62 (bt, J=5.6 Hz, 2H), 2.79 (t, J=4.8 Hz, 2H), 3.31 (t, J=6.4 Hz, 8H), 3.47-3.34 (m, 4H). (see Schickaneder, C.; Heinemann, F. W.; Alsfasser, R. “Copper II Complexes of the Tetraazamacrocyclic Tertiary Amide Ligand Alanyl-Cyclam,” Eur. J. Chem. 2006, 2357-2363)
Reference: [1] Patent: US2014/243397, 2014, A1, . Location in patent: Paragraph 0178-0180
  • 20
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  • [ 170161-28-1 ]
  • [ 170161-27-0 ]
Reference: [1] Patent: CN105237526, 2016, A, . Location in patent: Paragraph 0021
  • 21
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  • [ 24424-99-5 ]
  • [ 170161-28-1 ]
  • [ 170161-29-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 2, p. 229 - 241
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 2, p. 229 - 241
  • 22
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 28, p. 4995 - 4998
[2] Tetrahedron Letters, 1998, vol. 39, # 8, p. 853 - 856
[3] Tetrahedron Letters, 1998, vol. 39, # 8, p. 853 - 856
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