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Chemical Structure| 1395786-21-6 Chemical Structure| 1395786-21-6

Structure of 1395786-21-6

Chemical Structure| 1395786-21-6

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Product Details of [ 1395786-21-6 ]

CAS No. :1395786-21-6
Formula : C15H23NO4
M.W : 281.35
SMILES Code : O=C(OCC1[C@@]2([H])CCC#CCC[C@@]12[H])NCCOCCO
MDL No. :MFCD32641821

Safety of [ 1395786-21-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 1395786-21-6 ]

* 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 [ 1395786-21-6 ]

[ 1395786-21-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1426827-79-3 ]
  • [ 929-06-6 ]
  • [ 1395786-21-6 ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine; In dichloromethane; at 20℃; for 1.5h; <strong>[1426827-79-3](1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate</strong> (29-1 , 16.35 g, 56.13 mmol, 1 eq.) was dissolved in DCM (400 ml). 2-(2-aminoethoxy)ethanol (6.76 ml, 67.35 mmol, 1.2 eq.) was then added followed by triethylamine (23.47 ml, 168.39 mmol, 3 eq.). The resulting pale yellow solution was stirred at rt for 90 min. The reaction mixture was concentrated in vacuo and the residue was co-evaporated once with acetonitrile (400 ml_). The resulting oil was dissolved in EtOAc (400mL) and washed three times with water (200 ml_). The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography over silica (50% 88% EtOAc in heptane) to give the product as a pale yellow oil (1 1.2 g, 39.81 mmol, 71 %). 1 H-NMR (400 MHz, CDCIs) d 5.14-4.89 (bs, 1 H). 4.17 (d, J = 8.0 Hz, 2H,), 3.79-3.68 (m, 2H), 3.64-3.50 (m, 4H), 3.47-3.30 (m, 2H), 2.36-2.14 (m, 6H), 2.03-1.84 (bs, 1 H), 1.68-1.49 (m, 2H), 1.37 (quintet, J = 8.0 Hz, 1 H), 1.01-0.89 (m, 2H).
71% With triethylamine; In dichloromethane; at 20℃; for 1.5h; To a solution of (1R,8S,9S)-bicyclo[6.1 0]non-4-yn-9-ylmethyl /V-succinimidyl carbonate (108) (16.35 g, 56.13 mmol) in DCM (400 ml) were added 2-(2-aminoethoxy)ethanol (140) (6.76 ml, 67.35 mmol) and triethylamine (23.47 ml, 168.39 mmol). The resulting pale yellow solution was stirred at rt for 90 min. The mixture was concentrated in vacuo and the residue was co-evaporated once with acetonitrile (400 ml_). The resulting oil was dissolved in EtOAc (400 ml_) and washed with H2O (3 c 200 ml_). The organic layer was concentrated in vacuo. The residue was purified by silica gel column chromatography (50% 88% EtOAc in heptane) and gave 141 (11.2 g, 39.81 mmol, 71% yield) as a pale yellow oil. -NMR (400 MHz, CDCI3): d (ppm) 5.01 (br s, 1 H), 4.17 (d, 2H, J = 12.0 Hz), 3.79-3.68 (m, 2H), 3.64-3.50 (m, 4H), 3.47-3.30 (m, 2H), 2.36-2.14 (m, 6H), 1.93 (br s, 1 H), 1.68- 1.49 (m, 2H), 1.37 (quintet, 1 H, J = 8.0 Hz), 1.01-0.89 (m, 2H).
71% With triethylamine; In dichloromethane; at 20℃; for 1.5h; To a solution of (1R,8S,9S)-bicyclo[6.1 0]non-4-yn-9-ylmethyl /V-succinimidyl carbonate (108) (16.35 g, 56.13 mmol) in DCM (400 ml) were added 2-(2-aminoethoxy)ethanol (140) (6.76 ml, 67.35 mmol) and triethylamine (23.47 ml, 168.39 mmol). The resulting pale yellow solution was stirred at rt for 90 min. The mixture was concentrated in vacuo and the residue was co-evaporated once with acetonitrile (400 mL). The resulting oil was dissolved in EtOAc (400 mL) and washed with H2O (3c200 mL). The organic layer was concentrated in vacuo. The residue was purified by silica gel column chromatography (50% 88% EtOAc in heptane) and gave 141 (11.2 g, 39.81 mmol, 71% yield) as a pale yellow oil.1H-NMR (400 MHz, CDCI3): d (ppm) 5.01 (br s, 1 H), 4.17 (d, 2H, J = 12.0 Hz), 3.79-3.68 (m, 2H), 3.64-3.50 (m, 4H), 3.47-3.30 (m, 2H), 2.36-2.14 (m, 6H), 1.93 (br s, 1 H), 1 .68- 1 .49 (m, 2H), 1 .37 (quintet, 1 H, J = 8.0 Hz), 1 .01-0.89 (m, 2H).
71% With triethylamine; In dichloromethane; at 20℃; for 1.5h; To a solution of (1R,8S,9S)-bicyclo[6.1 0]non-4-yn-9-ylmethyl /V-succinimidyl carbonate (108) (16.35 g, 56.13 mmol) in DCM (400 ml) were added 2-(2-aminoethoxy)ethanol (140) (6.76 ml, 67.35 mmol) and triethylamine (23.47 ml, 168.39 mmol). The resulting pale yellow solution was stirred at rt for 90 min. The mixture was concentrated in vacuo and the residue was co-evaporated once with acetonitrile (400 ml_). The resulting oil was dissolved in EtOAc (400 ml_) and washed with H2O (3 c 200 ml_). The organic layer was concentrated in vacuo. The residue was purified by silica gel column chromatography (50% 88% EtOAc in heptane) and gave 141 (11.2 g, 39.81 mmol, 71% yield) as a pale yellow oil. -NMR (400 MHz, CDCI3): d (ppm) 5.01 (br s, 1 H), 4.17 (d, 2H, J = 12.0 Hz), 3.79-3.68 (m, 2H), 3.64-3.50 (m, 4H), 3.47-3.30 (m, 2H), 2.36-2.14 (m, 6H), 1.93 (br s, 1 H), 1.68-1.49 (m, 2H), 1.37 (quintet, 1 H, J = 8.0 Hz), 1.01-0.89 (m, 2H).

 

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