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Chemical Structure| 1125-99-1 Chemical Structure| 1125-99-1

Structure of 1125-99-1

Chemical Structure| 1125-99-1

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Product Details of [ 1125-99-1 ]

CAS No. :1125-99-1
Formula : C10H17N
M.W : 151.25
SMILES Code : C1(N2CCCC2)=CCCCC1
MDL No. :MFCD00003163

Safety of [ 1125-99-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 1125-99-1 ]

* 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 [ 1125-99-1 ]

[ 1125-99-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1125-99-1 ]
  • [ 107-14-2 ]
  • [ 42185-27-3 ]
YieldReaction ConditionsOperation in experiment
34% General procedure: Following the procedures of Stork,15 the cycloketone and pyrrolidine (1.1equiv) were dissolved in benzene or toluene (300mLmol-1 ketone; toluene for n>1) and refluxed for 5-10h (cyclopentanone and -hexanone) or 24-48h (cycloheptanone and -octanone). Excess pyrrolidine and solvent were removed under reduced pressure and the yellow to brown oily residue was directly used for further reactions. For medium-sized rings a small amount of p-toluenesulfonic acid was added (n>1). (0024) Next, the enamine (typically 5-20g) was dissolved in anhydrous dioxane (400mLmol-1) under an argon atmosphere. Then the electrophile (1.5equiv; chloroacetonitrile for compounds 1, 3, 5 and 7, or acrylonitrile for compounds 2, 4, 6 and 8) was added in one shot using a syringe. Occasionally, more electrophile was added in case of stagnant reactions. The mixture was refluxed for 10-48h until complete conversion of the enamine could be detected by GC-MS. Subsequently, water (200mLmol-1) was added and the biphasic mixture was heated to reflux for 30-60min. Dioxane was then removed by rotary evaporation and the residue was partitioned between EtOAc (2mLmmol-1) and 2N HCl (0.5mLmmol-1). The aqueous phase was extracted with EtOAc (4× same volume as before) and the pooled extracts were dried over sodium sulfate and concentrated under reduced pressure. Purification of the brown crude oils was performed on MPLC or via distillation.
  • 2
  • [ 1125-99-1 ]
  • [ 7731-02-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; N-Cyclohexylpyrrolidine was synthesized by hydrogenation of 1-pyrrolidino-1-cyclohexene (Sigma-Aldrich) per the teachings in Example 7 of U.S. Pat. No. 6,544,495 to Saleh Elomari.
References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 10796 - 10808.
[2]Organometallics,2018,vol. 37,p. 2665 - 2668.
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2001,vol. 170,p. 197 - 203.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2001,vol. 40,p. 152 - 156.
[5]Journal of the Chemical Society. Chemical communications,1981,p. 611 - 612.
[6]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1985,vol. 39,p. 187 - 190.
[7]Chemistry Letters,1987,p. 1275 - 1278.
[8]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 239 - 242.
[9]Chemistry - A European Journal,2017,vol. 23,p. 6056 - 6068.
[10]Journal of the Chemical Society. Perkin transactions I,1985,p. 437 - 440.
[11]Journal of Fluorine Chemistry,1989,vol. 43,p. 67 - 86.
[12]Journal of Organometallic Chemistry,1987,vol. 320,p. 163 - 170.
[13]Journal of Organic Chemistry,2000,vol. 65,p. 8326 - 8332.
[14]Tetrahedron Letters,2008,vol. 49,p. 7290 - 7293.
[15]Tetrahedron Letters,2010,vol. 51,p. 3762 - 3764.
[16]Patent: US2011/130610,2011,A1 .Location in patent: Page/Page column 8.
[17]Chemistry - A European Journal,2013,vol. 19,p. 2059 - 2066.
[18]Chemistry - A European Journal,2015,vol. 21,p. 12456 - 12464.
[19]Chemistry - A European Journal,2015,vol. 21,p. 12449 - 12455.
[20]Organometallics,2016,vol. 35,p. 847 - 850.
[21]Angewandte Chemie - International Edition,2016,vol. 55,p. 5526 - 5530.
    Angew. Chem.,2016,vol. 128,p. 5616 - 5620,5.
  • 3
  • [ 1125-99-1 ]
  • [ 590-17-0 ]
  • [ 42185-27-3 ]
  • 4
  • [ 1125-99-1 ]
  • [ 114078-88-5 ]
  • [ 82132-68-1 ]
  • 5
  • [ 1125-99-1 ]
  • [ 5424-47-5 ]
  • [ 78659-38-8 ]
  • 6
  • [ 1125-99-1 ]
  • [ 5424-47-5 ]
  • [ 1570-16-7 ]
 

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