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[ CAS No. 25125-21-7 ]

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Chemical Structure| 25125-21-7
Chemical Structure| 25125-21-7
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CAS No. :25125-21-7 MDL No. :MFCD04038630
Formula : C6H10O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :98.14 g/mol Pubchem ID :1514122
Synonyms :

Safety of [ 25125-21-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P273-P301+P312+P330-P501 UN#:N/A
Hazard Statements:H302-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25125-21-7 ]

  • Upstream synthesis route of [ 25125-21-7 ]
  • Downstream synthetic route of [ 25125-21-7 ]

[ 25125-21-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 7686-77-3 ]
  • [ 25125-21-7 ]
YieldReaction ConditionsOperation in experiment
85% With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 7 h; (a) cyclopent-3-enylmethanol (0164) (0165) To a suspension of lithium aluminum hydride (0.5083 g, 13.37 mmol, 3eq) in dry 100 ml THF at −78° C., cyclopent-3-enecarboxylic acid (0.5000 g, 4.45 mmol) was added drop wise over 1 h. The mixture was stirred for 6 h, and then quenched with 15 ml 1M NaOH. Mixture was stirred for an additional 2 h, then concentrated and up taken in diethyl ether and dried over MgSO4 to afford clear liquid (3.79 mmol, MW 98.14 g/mol, 85percent).1H NMR (300 MHz, CDCl3): δ 2.12-2.16; (ttt 1H), 2.49-2.53; (dd, 2H), 3.57-3.58 (d, 3H, 5.14 Hz), 5.69; (s, 2H).
Reference: [1] Tetrahedron, 2003, vol. 59, # 5, p. 671 - 676
[2] Journal of the American Chemical Society, 1982, vol. 104, p. 7105
[3] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 14, p. 2175 - 2178
[4] European Journal of Organic Chemistry, 2004, # 2, p. 289 - 303
[5] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 2, p. 451 - 452
[6] Journal of Organic Chemistry, 1989, vol. 54, # 2, p. 383 - 389
[7] Chemical Communications, 2013, vol. 49, # 100, p. 11758 - 11760
[8] Patent: US2016/206748, 2016, A1, . Location in patent: Paragraph 0164-0165
[9] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2784 - 2794
[10] Canadian Journal of Chemistry, 1968, vol. 46, p. 3758 - 3762
[11] Journal of Organic Chemistry, 1969, vol. 34, # 4, p. 860 - 864
[12] Journal of Organic Chemistry, 1970, vol. 35, # 8, p. 2803 - 2806
[13] Tetrahedron: Asymmetry, 1994, vol. 5, # 3, p. 337 - 338
[14] Journal of the American Chemical Society, 1982, vol. 104, # 3, p. 907 - 909
[15] Organic Letters, 2006, vol. 8, # 26, p. 5947 - 5950
[16] Synlett, 2006, # 10, p. 1583 - 1585
[17] Organic Letters, 2008, vol. 10, # 2, p. 169 - 171
[18] Patent: WO2003/99795, 2003, A1, . Location in patent: Page 58
[19] Patent: WO2003/99289, 2003, A2, . Location in patent: Page 63
[20] Patent: WO2010/62415, 2010, A1, . Location in patent: Page/Page column 22
[21] Patent: EP2433926, 2012, A1, . Location in patent: Paragraph 0078; 0080
[22] Patent: WO2012/31307, 2012, A1, . Location in patent: Page/Page column 21
[23] Patent: WO2016/106623, 2016, A1, . Location in patent: Page/Page column 115
[24] Patent: WO2016/106624, 2016, A1, . Location in patent: Page/Page column 78-79
  • 2
  • [ 58101-60-3 ]
  • [ 25125-21-7 ]
YieldReaction ConditionsOperation in experiment
100% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 18 h; To a solution of 2 (8.6 g, 68 mmol) in THF (40.0 mL) at 0° C. was added LAH (54 mL, 1M solution in THF) under N2 atmosphere. The mixture was stirred at ambient temperature for 18 hours. The reaction mixture was quenched with water and NaOH (10 w/t percent). The mixture was filtered through celite and solvent was removed to give compound 3 (6.6 g, 100percent).
95% With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; Inert atmosphere To a suspension of lithium aluminum hydride (15.2g, 0.40 mol) in anhydrous ether (1 L) at 0°C under nitrogen, was added the solution of methyl cyclopent-3-enecarboxylate (50 g, 0.40 mol) in ether (300 mL) dropwise over 5 hrs. The suspension was stirred at room temperature overnight. TLC indicated the completion of the reaction. The reaction was re-cooled to 0°C. Saturated solution of Na2S04 (32 mL) was added dropwise to quench the reaction. After the addition was complete, the mixture was stirred for another 3 hrs and was filtered through a pad of celite. Evaporation of solvent afforded cyclopent-3-enylmethanol 146-2 (37.3 g, 95 percent) as a colorless liquid.
Reference: [1] Patent: US2007/254952, 2007, A1, . Location in patent: Page/Page column 35
[2] Tetrahedron Asymmetry, 1994, vol. 5, # 9, p. 1649 - 1652
[3] Patent: WO2017/177326, 2017, A1, . Location in patent: Page/Page column 93; 94
[4] Synlett, 2005, # 5, p. 765 - 768
[5] Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 449 - 456
  • 3
  • [ 21622-01-5 ]
  • [ 25125-21-7 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With lithium aluminium tetrahydride; sodium hydroxide In tetrahydrofuran at -78℃; for 4 h; Inert atmosphere
Stage #2: With sodium hydroxide In water at 0 - 20℃;
To a cold (—78° C.) solution of 703 (7 g, 50 mmol) in dry THF (150 mE) was added EiA1H4 (1 M soln in THF, 25 mE, 25 mmol), and the reaction solution was stirred at —78° C.under argon for 4 h. Then the reaction solution was allowed towarm to 0° C., and 2.5 mE of water, 2.5 mE of 15percent NaOH,and 7.5 mE of water were added sequentially. Afier warming to tt., the precipitates were filtered through a celite, and the celite was washed with hot EtOAc. The combined filtrateswere washed with 0.1 N NaOH, and brine, dried (MgSO4),filtered, concentrated and dried in vacuo to give 4.294 g(84percent) of 704 as a pale yellow liquid. ‘H NMR (400 MHz, CDC13) ö 5.68 (s, 2H, 2CH=CH), 3.57 (d, J=6.0 Hz, 2H, CH2OH), 2.54-2.48 (m, 3H, CH+CH2), 2.15-2.10 (m, 2H, CH2).
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 5, p. 859 - 867
[2] Patent: US9180138, 2015, B2, . Location in patent: Page/Page column 58
[3] Patent: EP468119, 1992, A1,
  • 4
  • [ 88326-51-6 ]
  • [ 25125-21-7 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 26, p. 5947 - 5950
[2] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2784 - 2794
[3] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 2, p. 451 - 452
  • 5
  • [ 35357-77-8 ]
  • [ 25125-21-7 ]
Reference: [1] Synlett, 2005, # 5, p. 765 - 768
  • 6
  • [ 7686-78-4 ]
  • [ 25125-21-7 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2784 - 2794
[2] Journal of the American Chemical Society, 1982, vol. 104, # 3, p. 907 - 909
  • 7
  • [ 84646-68-4 ]
  • [ 25125-21-7 ]
Reference: [1] Synlett, 2005, # 5, p. 765 - 768
[2] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 2, p. 451 - 452
  • 8
  • [ 1781-66-4 ]
  • [ 25125-21-7 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 2, p. 383 - 389
  • 9
  • [ 21622-00-4 ]
  • [ 25125-21-7 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2784 - 2794
  • 10
  • [ 18325-74-1 ]
  • [ 25125-21-7 ]
Reference: [1] Patent: US9180138, 2015, B2,
  • 11
  • [ 3195-24-2 ]
  • [ 25125-21-7 ]
Reference: [1] Patent: US9180138, 2015, B2,
  • 12
  • [ 14320-38-8 ]
  • [ 25125-21-7 ]
Reference: [1] Journal of Organic Chemistry, 1969, vol. 34, # 4, p. 860 - 864
  • 13
  • [ 4492-41-5 ]
  • [ 25125-21-7 ]
Reference: [1] Journal of Organic Chemistry, 1969, vol. 34, # 4, p. 860 - 864
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