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[ CAS No. 22972-51-6 ]

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Chemical Structure| 22972-51-6
Chemical Structure| 22972-51-6
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CAS No. :22972-51-6 MDL No. :MFCD08460036
Formula : C10H16O Boiling Point : 216.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :152.23 g/mol Pubchem ID :11105550
Synonyms :

Safety of [ 22972-51-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22972-51-6 ]

  • Upstream synthesis route of [ 22972-51-6 ]
  • Downstream synthetic route of [ 22972-51-6 ]

[ 22972-51-6 ] Synthesis Path-Upstream   1~12

  • 1
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YieldReaction ConditionsOperation in experiment
74% at 180℃; Pyrolysis The 1S,2S,5R-N,N,2-trimethyl-2-hydroxy-5-isopropenylcyclohexamine oxide (1.430 g, 6.7 mmol) was heated in a Kugelrohr oven at 180 C under vacuum (1 mmHg) until all the solid residue had disappeared. The yellow distillate (1.317 g) was subjected to flash chromatography (2:3, diethyl ether: hexane) to obtain the colorless oil of 6 (0.752g, 74percent). Rf 0.32 (2:3 Et2O : hexane); [α]D26: +60 (1.0, CHCl3), lit.4 [α]D23: +53.8 (CHCl3); IR (SeZn): 3354 (m, broad, O–H), 2967 (m, C–H), 2935 (m, C-H), 2861 (m, C-H), 1644 (m, C=C), 1105 (s, C-O), 888 (s, C=C-H bend), 736 (s, C=C-H bend) cm-1; 1H NMR (500 MHz, CDCl3): δ 5.70 (1H, ddd, 3JH2-H3 10.0 Hz, 4JH2-H4 2.4 Hz, 4JH2-H6 1.4 Hz, H2), 5.65 (1H, ddd, 3JH3-H2 10.0 Hz, 3JH3-H4 2.4 Hz, 4JH3-H5 0.8 Hz, H3), 4.78 (1H, quin, 4JH9b-H10≈4JH9b-H4 1.6 Hz, H9b), 4.74 (1H, quin, 4JH9a-H10≈4JH9a-H4 0.88 Hz, H9a), 2.65 (1H, m, H4), 1.88-1.73 (2H, m, H5eq, H6eq), 1.73 (3H, s, H10), 1.66-1.51 (3H, m, H5ax, H6ax, OH), 1.29 (3H, s, H7) ppm; 13C NMR (125 MHz, CDCl3): 148.3 (C8), 134.1 (C2), 132.3 (C3), 110.7 (C9), 67.6 (C1), 43.6 (C4), 36.9 (C6), 29.6 (C7), 25.0 (C5), 21.0 (C10) ppm; LRMS (GC-MS): m/z 152 (M˙+, 2percent), 134 ([M-H2O]˙+, 11percent), 119 [M-CH3-H2O]˙+, 32percent), 91 (100percent), 79 (37percent), 77 (46percent); Anal. (C10H16O) Calc: C 78.90, H 10.59; Found: C 78.25, H 10.59, N <0.05.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 1, p. 52 - 54
  • 2
  • [ 5989-27-5 ]
  • [ 52154-82-2 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 2002, vol. 50, # 11, p. 1514 - 1516
[2] Patent: GB761686, 1954, ,
[3] Justus Liebigs Annalen der Chemie, 1964, vol. 674, p. 93 - 117
[4] Justus Liebigs Annalen der Chemie, 1964, vol. 674, p. 93 - 117
[5] Patent: US3014047, 1953, ,
  • 3
  • [ 6909-30-4 ]
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Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 13, p. 6489 - 6500
[2] Helvetica Chimica Acta, 2006, vol. 89, # 2, p. 231 - 239
[3] Tetrahedron Letters, 1995, vol. 36, # 6, p. 947 - 948
[4] Journal of Organic Chemistry, 1966, vol. 31, p. 1937 - 1945
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  • [ 78478-85-0 ]
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 6, p. 947 - 948
[2] Tetrahedron Letters, 2013, vol. 54, # 1, p. 52 - 54
  • 5
  • [ 1195-92-2 ]
  • [ 22972-51-6 ]
Reference: [1] Australian Journal of Chemistry, 1980, vol. 33, # 2, p. 451 - 454
[2] Tetrahedron Letters, 2013, vol. 54, # 1, p. 52 - 54
[3] Patent: US9155797, 2015, B2,
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  • [ 74756-11-9 ]
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Reference: [1] Australian Journal of Chemistry, 1980, vol. 33, # 2, p. 451 - 454
  • 7
  • [ 5989-27-5 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1965, vol. 687, p. 26 - 39
[2] Tetrahedron Letters, 2013, vol. 54, # 1, p. 52 - 54
  • 8
  • [ 42477-94-1 ]
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Reference: [1] Roczniki Chemii, 1963, vol. 37, p. 773 - 784
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  • [ 4942-88-5 ]
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Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 1937 - 1945
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  • [ 5989-27-5 ]
  • [ 99-48-9 ]
  • [ 18383-51-2 ]
  • [ 52154-82-2 ]
  • [ 22972-51-6 ]
  • [ 2102-62-7 ]
  • [ 10374-04-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 7, p. 1944 - 1949
[2] Archiv der Pharmazie, 1988, vol. 321, # 7, p. 385 - 389
[3] Journal of Organic Chemistry, 1994, vol. 59, # 5, p. 1135 - 1138
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  • [ 5989-27-5 ]
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Reference: [1] Journal of the American Chemical Society, 1998, vol. 120, # 29, p. 7252 - 7259
  • 12
  • [ 138-86-3 ]
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Reference: [1] Helvetica Chimica Acta, 1980, vol. 63, # 1, p. 76 - 94
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