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[ CAS No. 89743-52-2 ]

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Chemical Structure| 89743-52-2
Chemical Structure| 89743-52-2
Structure of 89743-52-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 89743-52-2 ]

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Product Details of [ 89743-52-2 ]

CAS No. :89743-52-2 MDL No. :MFCD23140962
Formula : C11H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :229.27 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 89743-52-2 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.64
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.32
TPSA : 64.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.99
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.23
Consensus Log Po/w : 1.79

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.85
Solubility : 3.2 mg/ml ; 0.014 mol/l
Class : Very soluble
Log S (Ali) : -2.76
Solubility : 0.403 mg/ml ; 0.00176 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.17
Solubility : 1.55 mg/ml ; 0.00675 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.61

Safety of [ 89743-52-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89743-52-2 ]

* 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 [ 89743-52-2 ]

[ 89743-52-2 ] Synthesis Path-Downstream   1~55

  • 1
  • [ 79-41-4 ]
  • [ 26690-80-2 ]
  • [ 89743-52-2 ]
  • 2
  • [ 89743-52-2 ]
  • [ 74-88-4 ]
  • N-methyl-N-tert-butyloxycarbonyl-(2-aminoethyl) methacrylate [ No CAS ]
  • 3
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 10, degree of polymerization = 28; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 4
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 16, degree of polymerization = 48; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 5
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 29, degree of polymerization = 30; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 6
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 40, degree of polymerization = 29; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 7
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 48, degree of polymerization = 29; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 8
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 60, degree of polymerization = 27; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 9
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 12, degree of polymerization = 17; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 10
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 20, degree of polymerization = 17; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 11
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 29, degree of polymerization = 18; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 12
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 37, degree of polymerization = 17; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 13
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 47, degree of polymerization = 19; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 14
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 55, degree of polymerization = 22; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 15
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 10, degree of polymerization = 4.1; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 16
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 17, degree of polymerization = 4.8; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 17
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 23, degree of polymerization = 5.6; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 18
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 34, degree of polymerization = 5.4; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 19
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 37, degree of polymerization = 6.4; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 20
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 41, degree of polymerization = 5.9; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 21
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 48, degree of polymerization = 6.8; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 22
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 51, degree of polymerization = 6.2; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 23
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 58, degree of polymerization = 5.9; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 24
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • polymer, mole percentage of n-butyl methacrylate: 52, degree of polymerization = 6; monomer(s): N-(tert-butoxycarbonyl)aminoethyl methacrylate; n-butyl methacrylate; methyl 3-mercaptopropionate [ No CAS ]
  • 25
  • [ 26690-80-2 ]
  • [ 920-46-7 ]
  • [ 89743-52-2 ]
YieldReaction ConditionsOperation in experiment
31% With triethylamine; In tetrahydrofuran; at 20℃;Cooling with acetone-dry ice; Synthesis of Boc-protected methacrylate monomer (1). Methacryloyl chloride (6.5 mL, 65 mmol) was added to tert-butyl N-(2-hydroxyethyl) carbamate (10 g, 62 mmol) in THF (100 mL) and triethylamine (9.5 mL, 68 mmol) cooled in a dry ice/acetone bath. The reaction mixture was allowed to warm at room temperature overnight, and the resultant precipitate was filtered off. The filtrate was concentrated by evaporation and the residue diluted with CH2Cl2, washed with water, 1N NaOH and brine. The organic layer was dried over Na2SO4, and the solvent was evaporated under reduced pressure. The product was purified by silica gel column chromatography (CH2Cl2 (90): EtOAc (10)). The obtained solid was recrystallized from CH2Cl2/hexane to give the product, 4.74 g (31% yield).
  • 26
  • [ 24424-99-5 ]
  • 2-aminoethylmethacrylate hydrochloride [ No CAS ]
  • [ 89743-52-2 ]
  • 27
  • α-(2-bromoisobutyrate)-ω-O-methyl-poly(ethylene glycol) [ No CAS ]
  • [ 89743-52-2 ]
  • ω-methylpoly(ethylene glycol)-b-poly[2-[N-(tert-butoxycarbonyl)amino]ethyl methacrylate] [ No CAS ]
  • 28
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=2000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=3100, Mw=3800, polydispersity index=1.23 (gel permeation chromatography) [ No CAS ]
  • 29
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=2000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=4500, Mw=5900, polydispersity index=1.31 (gel permeation chromatography) [ No CAS ]
  • 30
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=2000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=5300, Mw=7000, polydispersity index=1.33 (gel permeation chromatography) [ No CAS ]
  • 31
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=2000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=6000, Mw=8100, polydispersity index=1.35 (gel permeation chromatography) [ No CAS ]
  • 32
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=2000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=6600, Mw=8800, polydispersity index=1.33 (gel permeation chromatography) [ No CAS ]
  • 33
  • [ 20769-85-1 ]
  • [ 2867-47-2 ]
  • polyethylene glycol monomethyl ether, Mn=3000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate-co-dimethylaminoethyl methacrylate), atom transfer radical polymerization, Mn=5100, Mw=5800, polydispersity index=1.13 (gel permeation chromatography) [ No CAS ]
  • 34
  • [ 20769-85-1 ]
  • [ 2867-47-2 ]
  • polyethylene glycol monomethyl ether, Mn=3000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate-co-dimethylaminoethyl methacrylate), atom transfer radical polymerization, Mn=5500, Mw=6700, polydispersity index=1.20 (gel permeation chromatography) [ No CAS ]
  • 35
  • [ 20769-85-1 ]
  • [ 2867-47-2 ]
  • polyethylene glycol monomethyl ether, Mn=3000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate-co-dimethylaminoethyl methacrylate), atom transfer radical polymerization, Mn=5700, Mw=6700, polydispersity index=1.17 (gel permeation chromatography) [ No CAS ]
  • 36
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=3000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=4400, Mw=5200, polydispersity index=1.18 (gel permeation chromatography) [ No CAS ]
  • 37
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=3000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=5200, Mw=6100, polydispersity index=1.18 (gel permeation chromatography) [ No CAS ]
  • 38
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=3000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=6200, Mw=7000, polydispersity index=1.14 (gel permeation chromatography) [ No CAS ]
  • 39
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=3000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=6400, Mw=7400, polydispersity index=1.17 (gel permeation chromatography) [ No CAS ]
  • 40
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=3000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=7100, Mw=8500, polydispersity index=1.20 (gel permeation chromatography) [ No CAS ]
  • 41
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=5000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=6200, Mw=7300, polydispersity index=1.17 (gel permeation chromatography) [ No CAS ]
  • 42
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=5000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=6900, Mw=8100, polydispersity index=1.17 (gel permeation chromatography) [ No CAS ]
  • 43
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=5000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=7500, Mw=9000, polydispersity index=1.20 (gel permeation chromatography) [ No CAS ]
  • 44
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=5000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=8000, Mw=9700, polydispersity index=1.21 (gel permeation chromatography) [ No CAS ]
  • 45
  • [ 20769-85-1 ]
  • polyethylene glycol monomethyl ether, Mn=5000 [ No CAS ]
  • [ 89743-52-2 ]
  • poly(ethylene glycol)-block-poly(aminoethyl methacrylate), atom transfer radical polymerization, Mn=8800, Mw=10500, polydispersity index=1.19 (gel permeation chromatography) [ No CAS ]
  • 46
  • [ 2935-90-2 ]
  • [ 97-88-1 ]
  • [ 89743-52-2 ]
  • poly(n-butyl methacrylate-co-N-(tert-butoxycarbonyl)aminoethyl methacrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With 2,2'-azobis(isobutyronitrile); In acetonitrile; at 60℃; Boc-protected polymers: <strong>[89743-52-2]N-(tert-butoxycarbonyl)aminoethyl methacrylate</strong> and n-butyl methacrylate (0.435 mmol total) were dissolved in acetonitrile (0.5 mL) containing AIBN (0.716 mg, 4.35 μmol) and methyl 3-mercaptopropionate as a chain transfer agent and purged with Ar for 2 minutes. The reaction mixture was stirred at 60 C. overnight, and the solvent was evaporated off. The oily residue was diluted with CH2Cl2 and dropped into hexane. The obtained precipitate was collected by centrifugation and dried under vacuum. The mole percentage of butyl groups (MPBu) for the polymers was calculated via integration ratio of the signals from methylene protons of the monomer side chains in 1H NMR spectra (CDCl3). The DP was determined by integration of the signals from methylene protons of the side chains relative to those from methyl protons of MMP at the polymer terminal. 1H NMR (500 MHz, CDCl3) for the representative polymer (MPBu=29 and DP=30): δ 4.2-3.8 (bm, 59.49H), 3.691 (s, 3H), 3.390 (bs, 42.44H), 2.8-2.5 (m, 5.28H), 2.2-0.8 (m, 427.92H). Characterization results are summarized in Tables 5-1 and 5-2.
  • 47
  • [ 2935-90-2 ]
  • [ 97-63-2 ]
  • [ 89743-52-2 ]
  • poly(ethyl methacrylate-co-N-(tert-butoxycarbonyl)aminoethyl methacrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With 2,2'-azobis(isobutyronitrile); In 1,4-dioxane; at 60℃; Synthesis of amphiphilic polymethacrylate copolymers (6). Monomers 1 and 4 (0.435 mmol total) were dissolved in dioxane or acetonitrile (0.5 mL) containing AIBN (0.716 mg, 4.35 pmol) and methyl 3-mercaptopropionate as a chain transfer agent and purged with Ar for 2 minutes. The reaction mixture was stirred at 60 C. overnight, and the solvent was evaporated off. The oily residue was diluted with CH2Cl2 and dropped into hexane. The obtained precipitate was collected by filtration and dried under vacuum. Monomer compositions for the resultant copolymer (polymer 5) were calculated via integration of the signals from methylene protons of the side chains in 1H NMR spectra in CDCl3.; Synthesis of Polymethacrylate Random Copolymers. Monomer 1 was polymerized with comonomers 4 bearing different hydrophobic groups in the presence of a thiol as a CTA (Scheme 3). R=ethyl, butyl, hexyl, isobutyl, or benzyl. In order to make a diverse library of polymers, feed ratios of monomer 1 to comonomers and CTA concentrations were varied. Table 2 shows the characterization results for copolymers 5 with ethyl methacrylate or benzyl methacrylate polymerized in the presence of 10 mol % of CTA relative to the total amount of monomers. 1H NMR analysis for the copolymers detemined the average monomer compositions of the polymers and their DPs. The monomer compostions in the resultant polymers were close to the feed compositions, and the DPs for both polymers were quite similar. The copolymers 5 were deprotected by TFA to give cationic polymers 6. The polymers were readily soluble to water.
  • 48
  • [ 2935-90-2 ]
  • [ 89743-52-2 ]
  • poly(N-(tert-butoxycarbonyl)aminoethyl methacrylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With 2,2'-azobis(isobutyronitrile); In 1,4-dioxane; at 60℃; The molecular weights of the polymers were controlled using a chain transfer agent (CTA) during the radical polymerizations. To determine the degree of polymerization at various concentrations of CTA, Boc-protected amine monomer 1 was polymerized with n-butyl methacrylate using an azobisbutyronitrile (AIBN) radical initiator in the presence of methyl 3-mercaptpropionate as a chain transfer agent (CTA), to give Boc-protected polymer 2 (Scheme 2).
  • 50
  • [ 24424-99-5 ]
  • [ 141-43-5 ]
  • [ 920-46-7 ]
  • [ 89743-52-2 ]
YieldReaction ConditionsOperation in experiment
Under 2-8 Pa argon Ar conditions, 2.18 g of di-tert-butyl dicarbonate BOC was dissolved in 15 mL of acetonitrile MeCN. Then, a solution of 611 mg of ethanolamine dissolved in 15 mL of MeCN was added, stirred at room temperature for 0.5 h, and concentrated to 10 g after separation, and then under ice bath and 2-10 Pa of Ar gas. Re-dissolved in 100 mL of dichloromethane and added 16.2 mL of N,N-diisopropylethylamine EDIA. After stirring for 0.5 h, 6.7 mL of methacryloyl chloride MA was added dropwise. Stir in an ice bath for 0.5 h and return to room temperature for 12 h. Washing with a small amount of dichloromethane and a large amount of n-hexane, vacuum drying to obtain MA-NHBOC;
  • 51
  • [ 26690-80-2 ]
  • [ 18358-13-9 ]
  • [ 89743-52-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 8h; General procedure: The monomer 2-(hexamethyleneimino) ethyl methacrylate (C7A-MA) was synthesized according to previous reports (K. J. Zhou, Y. G. Wang. X. N. Huang, K. Luby-Phelps, B. D. Sumer, J. M. Gao, Angew Chem Int Edit 2011, 50, 6109). Briefly, 7 1H-azepine-1-ethanol, hexahydro- (5.0 g, 34.5 mmol) and 8 triethylamine (TEA, 7.0 g, 69 mmol) was dissolved in 100 mL dried THF and cooled to 0 C. in an ice bath. 9 Methacryloyl chloride (4.0 g, 38.5 mmol) was dissolved in 15 mL dried THF and slowly dropped into the previous solution. The reaction was moved to room temperature and stirred for 8 h, then filtered to remove TEA salt. The filtrate was condensed by rotary evaporation and further purified by flash chromatography (Hex:EtOAc=2:1). C7A-MA: 1H NMR (TMS, CDCl3, ppm): 6.1 (s, 111), 5.6 (s, 1H), 4.2 (t, 2H), 2.8 (s, 2H), 2.7 (s, 4H), 2.0 (s, 3H), 1.8 (s, 4H), and 1.6 (s, 4H).
  • 53
  • [ 760-93-0 ]
  • [ 26690-80-2 ]
  • [ 89743-52-2 ]
YieldReaction ConditionsOperation in experiment
With dmap; In dichloromethane; at 20℃; for 3h;Cooling with ice; Dissolve Boc-2-ethanolamine (5 g) and DMAP (4.2 g) in 100 mL of anhydrous dichloromethane, add methacrylic anhydride (5.2 g) dropwise in an ice bath, remove the ice bath, react at room temperature for 3 h, spin off tetrahydrofuran, add 200 mL of ethyl acetate, and washed three times each with 3% HCl, saturated sodium bicarbonate, and saturated brine, dried over anhydrous sodium sulfate, and spin-dried to obtain a white solid 6.
  • 54
  • [ 89743-52-2 ]
  • C24H41N3O8 [ No CAS ]
  • 55
  • [ 103290-07-9 ]
  • [ 89743-52-2 ]
  • C15H26N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Dissolve Boc-L-2-aminobutyric acid (10 g), N-hydroxysuccinimide (NHS, 8.5 g) and DMAP (9.1 g) in 100 mL of dry dichloromethane, add dicyclohexylcarbodiimide (DCC, 15.2 g) in dichloromethane (40 mL) dropwise in an ice bath, remove the ice bath, react at room temperature overnight, filter to remove dicyclohexylurea (DCU), concentrate the filtrate, and to recrystallize Boc-L-2-aminobutyric acid-NHS ester as white crystals under ethyl acetate/n-hexane. Compound 6 (3.88 g) was dissolved in 10 mL of dichloromethane, and an equal volume of trifluoroacetic acid was added to deprotect it. The raw materials disappeared by TLC monitoring and concentrated. 20 mL of dichloromethane and 8 mL of triethylamine were added, and a solution of Boc-L-2-aminobutyric acid-NHS ester (4.4 g) in dichloromethane was added dropwise at room temperature, and the reaction was carried out for 3 hours, spin dry to remove dichloromethane. Add 100 mL of ethyl acetate, washed three times each with 3% HCl, saturated sodium bicarbonate, and saturated brine, dried over anhydrous sodium sulfate, and spin-dried to obtain a colorless viscous liquid 7.
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tert-Butyl 3-(2-((tert-butoxycarbonyl)amino)ethoxy)propanoate

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Chemical Structure| 441752-75-6

[ 441752-75-6 ]

tert-Butyl (2-(allyloxy)ethyl)carbamate

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Chemical Structure| 89760-46-3

[ 89760-46-3 ]

2-((tert-Butoxycarbonyl)amino)ethyl dec-9-enoate

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Chemical Structure| 145119-18-2

[ 145119-18-2 ]

tert-Butyl 3-(2-((tert-butoxycarbonyl)amino)ethoxy)propanoate

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Amides

Chemical Structure| 89760-46-3

[ 89760-46-3 ]

2-((tert-Butoxycarbonyl)amino)ethyl dec-9-enoate

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Chemical Structure| 145119-18-2

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tert-Butyl 3-(2-((tert-butoxycarbonyl)amino)ethoxy)propanoate

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Chemical Structure| 441752-75-6

[ 441752-75-6 ]

tert-Butyl (2-(allyloxy)ethyl)carbamate

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Chemical Structure| 89760-46-3

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2-((tert-Butoxycarbonyl)amino)ethyl dec-9-enoate

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Chemical Structure| 145119-18-2

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tert-Butyl 3-(2-((tert-butoxycarbonyl)amino)ethoxy)propanoate

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Amines

Chemical Structure| 89760-46-3

[ 89760-46-3 ]

2-((tert-Butoxycarbonyl)amino)ethyl dec-9-enoate

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Chemical Structure| 145119-18-2

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tert-Butyl 3-(2-((tert-butoxycarbonyl)amino)ethoxy)propanoate

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Chemical Structure| 441752-75-6

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tert-Butyl (2-(allyloxy)ethyl)carbamate

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Chemical Structure| 89760-46-3

[ 89760-46-3 ]

2-((tert-Butoxycarbonyl)amino)ethyl dec-9-enoate

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Chemical Structure| 145119-18-2

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tert-Butyl 3-(2-((tert-butoxycarbonyl)amino)ethoxy)propanoate

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