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[ CAS No. 51411-04-2 ] {[proInfo.proName]}

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Chemical Structure| 51411-04-2
Chemical Structure| 51411-04-2
Structure of 51411-04-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51411-04-2 ]

CAS No. :51411-04-2 MDL No. :MFCD00181399
Formula : C14H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :GCUCIFQCGJIRNT-UHFFFAOYSA-N
M.W : 255.23 Pubchem ID :2120
Synonyms :
AY-22284;NSC 299132

Calculated chemistry of [ 51411-04-2 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 13
Fraction Csp3 : 0.07
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 71.01
TPSA : 76.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.83
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 1.04
Log Po/w (MLOGP) : 1.68
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 1.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.03
Solubility : 0.241 mg/ml ; 0.000944 mol/l
Class : Soluble
Log S (Ali) : -3.18
Solubility : 0.169 mg/ml ; 0.000663 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.0482 mg/ml ; 0.000189 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.98

Safety of [ 51411-04-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51411-04-2 ]

* 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 [ 51411-04-2 ]

[ 51411-04-2 ] Synthesis Path-Downstream   1~83

  • 1
  • [ 353262-66-5 ]
  • [ 51411-04-2 ]
  • 4
  • [ 81-84-5 ]
  • [ 56-40-6 ]
  • [ 51411-04-2 ]
YieldReaction ConditionsOperation in experiment
89.4% In N,N-dimethyl-formamide; at 90℃; for 8h; Benzo[de]isochromene-1,3-dione (3.9 6g, 0.02 mol) and glycine (1.50 g, 0.02 mol) were added into a three-neck flask with 40 mL DMF in it. The reaction mixture was stirred for 8 h in an oil-bath at 90C. After standing overnight, the mixture was filtrated to get the pale yellow powder. After washed with ethanol till the filter liquor turned colorless, the powder was recrystallized in a small portion of DMF. Yield: 89.4%; mp: 270.8-273.4C. 1H NMR (dimethyl sulfoxide-d6, ppm): delta 13.03 (s, 1H, COOH); 8.60 (d, 2H, J =7.2 Hz, Ar-H); 8.54 (d, 2H, J = 7.1 Hz, Ar-H); 7.93 (dd, 2H, J = 7.4, 7.0 Hz, Ar-H); 4.74 (s, 2H, -CH2-). 13C NMR (dimethyl sulfoxide-d6, ppm): delta 179.81 (1C, COO); 173.50 (2C, C=O); 137.56 (2C), 135.25 (2C), 130.23 (1C), 127.76 (2C), 125.66 (1C), 121.85 (2C) (carbon protons of aryl groups), 40.78 (1C, -CH2-).
68.65% With triethylamine; In ethanol; for 6h;Reflux; General procedure: Fist, a terminal luminophore of the water-soluble peptide fluorescence material is synthesized by adding acid anhydride, glycine and triethylamine in an ethanol solvent to prepare a mixture, which is refluxed for 6 hours, and the above reaction is traced by thin-layer chromatography (TLC). After the reaction, the mixture is cooled to a room temperature, and most of the ethanol solvent is removed by a rotational vacuum concentrator. Then, a hydrochloric acid having a molar concentration of 1M is slowly added to precipitate a solid. After a suction filtration process, the solid is took out and purified by recrystallization, and a solid product is obtained by filtering. Various reactants of the terminal luminophore and the products obtained from these reactants are listed in Table 1. [table-us-00001-en] TABLE 1 Synthesis of various terminal luminophores by different acid anhydrides. abbreviation of triethylamine the product acid anhydride glycine (volume, (color, weight, (weight, mol) (weight, mol) mol) yield) 1,8-Naphthalic glycine triethylamine NI anhydride (1.7 g, (3.2 ml, foumula(IV-1) (1.5 g, 7.58 mmol) 22.67 mmol) 22.8 mmol) (white, 1.3278 g, 68.65%) 4-piperidine-1,8- glycine triethylamine PPNI naphthalimide (1.710 g, (3.19 mol, foumula (IV-2) (2.142 g, 7.6 mmol) 22.8 mmol) 22.8 mmol) (yellow, 1.60 g, 66%) 4-pyrrolidino-1,8- glycine triethylamine PRNI naphthalimide (1.125 g, (2.1 ml, foumula (IV-3) (1.335 g, 5 mmol) 15 mmol) 15 mmol) (orange, 0.21 g, 13%) 4-azepanyl-1,8- glycine triethylamine AHNI naphthalimide (0.517 g, (0.97 ml, foumula (IV-4) (0.407 g, 6.9 mmol) 6.9 mmol) (yellow, 0.462 g, 1.38 mmol) 91%) 4-azocanylacetic- glycine triethylamine AONI 1,8-naphthalimide (0.517 g, (0.97 ml, (IV-5) (0.428 g, 6.9 mmol) 6.9 mmol) (yellow, 0.460 g, 1.38 mmol) 91%) (0059) NI has a structure of formula (IV-1): (0060) The product of formula (IV-1) is under structure analysis by an nuclear magnetic resonance (1H NMR), and the NMR spectroscopy is shown below: (0061) 1H NMR (300 MHz, DMSO-d6) delta=4.78 (s, 2H; CH2), 7.94 (dd, J(H,H)=7.8, 7.8 Hz, 2H; CH), 8.55 (d, J(H,H)=7.8 Hz, 2H; CH), 8.56 (d, J(H,H)=7.8 Hz, 2H; CH). The structure of formula (IV-1) is referred to NI (1,8-naphthalimide-N-acetic acid) in order to facilitate the subsequent descriptions.
With hydrogenchloride; In water; N,N-dimethyl-formamide; at 85℃; for 24h; 1-naphthalene anhydride (198 mg, 1 mmol), glycine (90 mg, 1.2 mmol) was added to DMF (5 ml)85 reaction 24h The reaction is finished cooling,1M hydrochloric acid (2 ml) was added, filtered, washed and dried to give a pale yellow solid.
In N,N-dimethyl-formamide; at 60℃; A mixture of 1,8-naphthalic anhydride (1.00 mmol) andglycine (1.10 mmol) was added in DMF (5 mL) and themixture was stirred at 60 C for several hours (TLC controlin a 2:1 n-hexane:ethyl acetate solvent mixture). Aftercooling to room temperature, 20 mL water was added andthe solid Alrestatin was separated. The product was purifiedby recrystallization from ethanol and used for the next step(Donkor et al. 1998).
With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 5h; General procedure: The synthesis was initiated by heating 1,8-naphthalic anhydride 1,with glycine 5 in dry DMF at 100 C in the presence of triethyl amine asbase. The product obtained 6 (1 mmol) was then reacted with quinolinediamine 2 (1 mmol) using coupling reagents EDC (1.1 eq), HOBt(1.2 eq) and DIEA (2 eq) in anhydrous DMF for 1 h. The reaction wasmonitored using TLC and after its completion, water was added toquench the reaction. The desired products precipitated out of the reactionmixture which was filtered, washed with water and recrystallizedin ethanol to yield the desired conjugates.

  • 5
  • [ 98-10-2 ]
  • [ 51411-04-2 ]
  • N-[2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetyl]-benzenesulfonamide [ No CAS ]
  • 6
  • [ 14949-01-0 ]
  • [ 51411-04-2 ]
  • [ 205536-87-4 ]
  • 7
  • [ 5455-59-4 ]
  • [ 51411-04-2 ]
  • N-[2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetyl]-2-nitro-benzenesulfonamide [ No CAS ]
  • 8
  • [ 121-52-8 ]
  • [ 51411-04-2 ]
  • N-[2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetyl]-3-nitro-benzenesulfonamide [ No CAS ]
  • 9
  • [ 6325-93-5 ]
  • [ 51411-04-2 ]
  • N-[2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetyl]-4-nitro-benzenesulfonamide [ No CAS ]
  • 10
  • [ 51411-04-2 ]
  • [ 205536-90-9 ]
  • 4-Amino-N-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetyl]-benzenesulfonamide [ No CAS ]
  • 11
  • [ 78052-77-4 ]
  • [ 51411-04-2 ]
  • 12
  • [ 64-19-7 ]
  • 2-<2-hydroxy-ethyl-benz<<i>de</i>>isoquinoline-1,3-dione [ No CAS ]
  • [ 51411-04-2 ]
  • 13
  • [ 771-61-9 ]
  • [ 51411-04-2 ]
  • [ 439913-28-7 ]
YieldReaction ConditionsOperation in experiment
87% With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 15h; [0064] DCC (155 mg, 0.75 mmol) was added to a DMF solution (5 mL) of NI-OH (192 mg, 0.75 mmol) and PfpOH (152 mg, 0.83 mmol) while ice cooling, and the reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (CH2Cl2) to give NI-OPfp (277 mg, 87%) as a red powder. <1>H NMR (CDCl3) delta 8.64 (d, J = 8 Hz, 2 H), 8.25 (d, J = 8 Hz, 2 H), 7.78 (t, J = 8 Hz, 2 H) , 5.29 (s, 2 H) .
  • 14
  • [ 476359-53-2 ]
  • [ 51411-04-2 ]
  • 16
  • [ 51411-04-2 ]
  • [ 636581-04-9 ]
  • 17
  • [ 51411-04-2 ]
  • diisopropyl-phosphoramidous acid 2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[2-(1,3-dioxo-1<i>H</i>,3<i>H</i>-benzo[<i>de</i>]isoquinolin-2-yl)-acetylamino]-5-(2,4-dioxo-3,4-dihydro-2<i>H</i>-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester [ No CAS ]
  • 18
  • [ 51411-04-2 ]
  • N-(diphenylmethyl)-N-hydroxy-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetamide [ No CAS ]
  • 20
  • [ 51411-04-2 ]
  • 2-(N-(2-((tert-butoxy)carbonylamino)ethyl)-2-(1,3-dioxo-1H-benz[de]isoquinoline-2(3H))acetylamino)acetic acid [ No CAS ]
  • 21
  • [ 51411-04-2 ]
  • [ 476359-54-3 ]
  • 23
  • [ 51411-04-2 ]
  • 3-Amino-N-[2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetyl]-benzenesulfonamide [ No CAS ]
  • 24
  • [ 51411-04-2 ]
  • N-{4-[2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetylsulfamoyl]-phenyl}-2-iodo-acetamide [ No CAS ]
  • 25
  • [ 51411-04-2 ]
  • ({4-[2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-acetylsulfamoyl]-phenylcarbamoyl}-methyl)-trimethyl-ammonium; chloride [ No CAS ]
  • 26
  • [ 51411-04-2 ]
  • N-(2-Propyleneiminooxycarbonylmethyl)-1,8-naphthalenedicarboximide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphorus pentachloride; trichlorophosphate; Example 1 N-(2-Propyleneiminooxycarbonylmethyl)-1,8-naphthalenedicarboximide STR79 Stage 1.1: Preparation of the acyl chloride A stirred mixture of 12.8 g (50 mmol) of N-hydroxycarbonylmethyl-1,8-naphthalenedicarboximide, 9.9 g (47.5 mmol) of phosphorus pentachloride and 20 ml of POCl3 was slowly heated to 75 C. and stirred at this temperature for a further 3 hours. Thereafter, the reaction mixture was evaporated to dryness and the crude product was further processed in the following stage, without purification.
  • 27
  • [ 51411-04-2 ]
  • [ 78052-77-4 ]
YieldReaction ConditionsOperation in experiment
With p-toluenesulfonic acid monohydrate; In ethanol; ethyl acetate; toluene; EXAMPLE 5 1,3-Dioxo-1H-benz[de]isoquinoline-2(3H)-acetic Acid Ethyl Ester (III, Z=H and R=C2 H5) A mechanically-stirred mixture of 1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid (125.0 g, 0.49 mole), p-toluenesulfonic acid hydrate (9.3 g, 0.049 mole), anhydrous pure ethanol (226 g, 288 ml, 0.49 mole) and dry toluene (750 ml) was heated at reflux for 16 hr in a Soxhlet apparatus in which the thimble was filled with hydrated alkali-aluminium silicate (3 A Molecular Sieves). The title compound was crystallized from the reaction mixture after cooling to room temperature. The crystals were collected and a second crop of crystals were obtained from the mother liquors. Recrystallization of the two crops of crystals from ethyl acetate gave the title compound; mp 160-162 C.; UV (MeOH) 232, 332 and 341 nm, epsilon=48,613, 13,470 and 12,920, respectively; IR (CHCl3) 1745, 1705 and 1665 cm-1; Anal. Calc'd.: C, 67.84%; H, 4.63%; N, 4.94%; Found: C, 67.89%; H, 4.60 %; N, 4.87%.
  • 28
  • [ 515-93-5 ]
  • [ 51411-04-2 ]
  • N-((2S,3R)-1,3-dihydroxybutan-2-yl)-2-(2-N-(benzo[de]-1,3-diketoisoquinolinyl))acetamide [ No CAS ]
  • 29
  • [ 135980-44-8 ]
  • [ 51411-04-2 ]
  • 30
  • [ 51411-04-2 ]
  • [ 165550-61-8 ]
  • [ 937041-02-6 ]
YieldReaction ConditionsOperation in experiment
13% Example 14; A mixture of 69.9 g (0.71 mol) of sodium tert-butoxide, 68.4 ml of diethylene glycol diethyl ether and 126.5 ml (0.85 mol) of DBU was heated to 60 C. in a Schlenk tube with stirring and under nitrogen. After 20 min, 17.6 g (0.035 mol) of N-(2,6-diisopropylphenyl)perylene-3,4-dicarboximide and, after a further 5 min, 18.0 g (0.071 mol) of N-(2-carboxyethyl)naphthalene-1,8-dicarboximide were added under nitrogen. The mixture was then heated to 120 C. under nitrogen and stirred at this temperature for 6 h.After cooling to room temperature, the reaction mixture was left to stand under air for about 12 h and then added to 3 l of water. The product precipitated in this way was filtered off, washed with water and dried, then acidified with 13% by weight hydrochloric acid, washed again with water and dried, and finally boiled first in methanol and then in ethanol, filtered off, washed with hot water and dried.4.34 g of I14 were obtained in the form of a blue solid, which corresponds to a yield of 13%.Analytical Data of I14:MS (FD): m/z (rel. int.)=733.2 (100%) [M+].
  • 31
  • Fmoc-Rink resin [ No CAS ]
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 51411-04-2 ]
  • [ 71989-31-6 ]
  • [ 71989-14-5 ]
  • [ 71989-18-9 ]
  • [ 71989-23-6 ]
  • [ 1083307-90-7 ]
  • 32
  • [ 110-86-1 ]
  • tetrakis(acetato)diaquadicopper(II) [ No CAS ]
  • [ 75-09-2 ]
  • [ 51411-04-2 ]
  • Cu2((1,8-naphthalimido)ethanoate)4(pyridine)2*2CH2Cl2 [ No CAS ]
  • 33
  • [ 67-56-1 ]
  • tetrakis(acetato)diaquadicopper(II) [ No CAS ]
  • [ 75-09-2 ]
  • [ 51411-04-2 ]
  • Cu2((1,8-naphthalimido)ethanoate)4(MeOH)2 [ No CAS ]
  • 34
  • [ 51411-04-2 ]
  • [ 76-87-9 ]
  • [ 108-88-3 ]
  • [ 1428247-20-4 ]
YieldReaction ConditionsOperation in experiment
75% for 10h;Reflux; Dean-Stark; A mixture of triphenyltin hydroxide (0.367 g, 1 mmol) and L1 (0.255 g, 1 mmol) was heated under reflux in toluene (50 mL) for 10 h in a Dean-Stark apparatus for azeotropic removal of the water formed in the reaction. After cooling to room temperature, the solution was filtered. The filtrate was gradually evaporated and the X-ray quality colorless crystals were obtained. Yield: 75%; mp: 255.7-258.0C. Anal. Calcd for C32H23NO4Sn·C7H8: C, 67.26; N, 2.01; H, 4.49%. Found: C, 67.38; N, 2.08; H, 4.38%. IR (cm-1): v(O=C) 1714; vas(COO) 1598; vs(COO) 1393; v(Sn-C) 581; nu(Sn-O) 437. 1H NMR (CDCl3, ppm): delta 8.37-8.31 (m, 4H, Ar-H: H5, H7, H9, H11); 7.66 (dd, 2H, J = 7.6, 7.0 Hz, Ar-H: H6, H10); 7.25-7.28 (m, 15H, Ph-H); 4.92 (s, 2H, -CH2-). 13CNMR (CDCl3, ppm): 179.78 (1C, COO); 167.79 (2C, C=O); 135.46 (2C, C5, C11), 133.69 (2C, C7, C9), 132.58 (1C, C8), 129.04 (3C, J1S119n-C13 = 424 Hz, J2S119n-C13 = 19 Hz, J3S119n-C13 = 63 Hz, C15, C21, C27), 128.82 (6C, C16, C20, C22, C26, C28, C32), 128.23 (6C, C17, C19, C23, C25, C29, C31), 127.51 (3C, C18, C24, C30), 125.30 (2C, C6, C10), 124.98 (1C, C13), 123.20 (2C, C4, C12) (carbon protons of aryl groups), 35.92 (1C, -CH2-).
  • 35
  • [ 51411-04-2 ]
  • [ 818-08-6 ]
  • [ 108-88-3 ]
  • (n-Bu<SUB>2</SUB>Sn)((1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetate)<SUB>2</SUB> toluene solvate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.5% for 10h;Reflux; Dean-Stark; General procedure: A mixture of triphenyltin hydroxide (0.367 g, 1 mmol) and L1 (0.255 g, 1 mmol) was heated under reflux in toluene (50 mL) for 10 h in a Dean-Stark apparatus for azeotropic removal of the water formed in the reaction. After cooling to room temperature, the solution was filtered. The filtrate was gradually evaporated and the X-ray quality colorless crystals were obtained.
  • 36
  • [ 280-57-9 ]
  • [ 51411-04-2 ]
  • 2C14H9NO4*C6H12N2 [ No CAS ]
  • 37
  • [ 100-76-5 ]
  • [ 51411-04-2 ]
  • C14H9NO4*C7H13N [ No CAS ]
  • 38
  • [ 51411-04-2 ]
  • [ 1619-34-7 ]
  • C14H9NO4*C7H13NO [ No CAS ]
  • 39
  • [ 110-85-0 ]
  • [ 51411-04-2 ]
  • 2C14H9NO4*C4H10N2 [ No CAS ]
  • 40
  • caesium hydroxide hydrate [ No CAS ]
  • [ 51411-04-2 ]
  • (1,8-naphthalimido)ethanoic acid [ No CAS ]
  • 41
  • [ 67-56-1 ]
  • gadolinium(III) chloride hexahydrate [ No CAS ]
  • [ 51411-04-2 ]
  • 3C14H8NO4(1-)*Gd(3+)*CH4O*H2O [ No CAS ]
  • 42
  • [ 67-56-1 ]
  • europium(III) chloride hexahydrate [ No CAS ]
  • [ 51411-04-2 ]
  • 3C14H8NO4(1-)*Eu(3+)*CH4O*H2O [ No CAS ]
  • 43
  • [ 51411-04-2 ]
  • [ 15485-31-1 ]
  • 2-(1-(4-ethoxyphenyl)-2-(4-nitrophenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio. 2-(1-(4-Ethoxyphenyl)-2-(4-nitrophenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (3a)White solid (Yield 75%); Rf = 0.86 (n-hexane: ethyl acetate= 7:3) Mp: 255-257 C; IR (KBr, cm-1): 1774 (CO beta-lactam), 1704 (CO Naph), 1666 (CO Naph); 1H-NMR (250MHz, DMSO-d6) delta 1.27 (3H, t, J = 6.7 Hz, CH3), 3.95 (2H,q, J = 6.7 Hz, CH2), 5.69 (1H, d, J = 2.7 Hz, H-4), 5.94(1H, d, J = 2.7 Hz, H-3), 6.91 (2H, d, J = 9.0 Hz, ArH),7.19 (2H, d, J = 9.0 Hz, ArH), 7.79-7.89 (4H, m, ArH),8.24 (2H, d, J = 9.0 Hz, ArH), 8.43-8.50 (4H, m, ArH);13C-NMR (62.5 MHz, DMSO-d6) delta 163.2 (CO beta-lactam),162.1 (CO Naph), 155.0, 147.4, 144.8, 134.8, 131.2, 131.1,130.5, 128.1, 127.4, 127.3, 123.9, 121.5, 118.2, 115.0,(aromatic carbons), 63.4 (C beta-lactam), 63.1 (C beta-lactam),58.0 (CH2-O), 14.5 (CH3); GC-MS m/z = 507 [M+]; Analysiscalculated for C29H21N3O6: C, 68.63; H, 4.17; N,8.28%. Found: C, 68.20; H, 4.60; N, 8.51%.
  • 44
  • [ 1749-03-7 ]
  • [ 51411-04-2 ]
  • 2-(2-(4-chlorophenyl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 45
  • [ 51411-04-2 ]
  • [ 14607-16-0 ]
  • 2-(2-(anthracen-9-yl)-1-(4-methoxyphenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 46
  • [ 51411-04-2 ]
  • [ 15485-32-2 ]
  • 2-(2-(4-chlorophenyl)-4-oxo-1-(p-tolyl)azetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 47
  • [ 51411-04-2 ]
  • [ 76712-19-1 ]
  • CCC [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 48
  • [ 51411-04-2 ]
  • [ 20459-90-9 ]
  • 2-(1-(naphthalen-1-yl)-2-(naphthalen-2-yl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 49
  • [ 51411-04-2 ]
  • [ 730-39-2 ]
  • 2-(2-(4-nitrophenyl)-4-oxo-1-(p-tolyl)azetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 50
  • [ 51411-04-2 ]
  • C14H10N2O4 [ No CAS ]
  • 2-(1-(benzo[d][1,3]dioxol-5-yl)-2-(4-nitrophenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 51
  • [ 339166-14-2 ]
  • [ 51411-04-2 ]
  • 22-(1-(3,4-dimethoxyphenyl)-2-(4-nitrophenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 52
  • [ 51411-04-2 ]
  • N-(2-Nitro-benzal)-2.4-dimethoxy-anilin [ No CAS ]
  • 2-(1-(2,4-dimethoxyphenyl)-2-(2-nitrophenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 53
  • [ 51411-04-2 ]
  • N-(3,4-dimethoxybenzylidene)benzo[d][1,3]dioxol-5-amine [ No CAS ]
  • 2-(1-(benzo[d][1,3]dioxol-5-yl)-2-(3,4-dimethoxyphenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 54
  • [ 1309683-87-1 ]
  • [ 51411-04-2 ]
  • 2-(1-(2,4-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)-4-oxoazetidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20℃; for 24h; General procedure: The appropriate aromatic imine (Schiff base) (1.00 mmol),triethylamine (5.00 mmol), 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (1.50 mmol), and tosylchloride (1.50 mmol) were added to anhydrous CH2Cl2(5 mL) stirred at 0 C, and the mixture was allowed to warmto room temperature for further stirring for 24 h (TLCcontrol in a 7:3 n-hexane:ethyl acetate solvent mixture). Themixture was then washed twice with 1N aqueous HClsolution (20 mL), and once with saturated aqueous NaHCO3solution (50 mL) and brine (20 mL). The organic layer wasdried over anhydrous Na2SO4 and the solvent removed toproduce the product as a crystal, which was then purified byrecrystallization from ethyl acetate and acetone in a 3:2volumetric ratio.
  • 55
  • [ 51411-04-2 ]
  • C14H16OSn [ No CAS ]
  • [ 71-43-2 ]
  • C84H74N2O12Sn4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% for 8h;Reflux; Dean-Stark; To a suspension of Bn2SnO (0.634 g, 2 mmol) in benzene (30 mL), HL (0.255 g, 1 mmol) was added. The mixture was stirred and heated under reflux for 8 h in a Dean-Stark apparatus for azeotropic removal of the water formed in the reaction. After filtering, clear solution was obtained. The filter liquor was evaporated in vacuum to give colorless crystals of complex 1. Yield: 70%; Mp: 266-268 C. Anal. Calcd for C96H86N2O12Sn4: C, 59.60; N, 1.45; H, 4.48%. Found: C, 59.68; N, 1.40; H, 4.38%. IR (cm-1): vas(COO) 1592; vs(COO) 1379; v(Sn-C) 586; v(Sn-O) 456. 1H NMR (DMSO-d6, ppm): delta 8.56-7.30 (m, 12H, Ar-H); 7.25-7.02 (m, 40H, Bn-H); 4.74 (s, 4H, N-CH2-); 2.72 (s, 2H, -OH); 2.63 (s, 16H, Ph-CH2-). 13C NMR (DMSO-d6, ppm): 176.43 (2C, COO); 162.09 (4C, C=O); 139.75 (8C, Bn-C); 138.21 (4C, Ar-C); 135.68 (4C, Ar-C); 130.13 (4C, Ar-C); 129.24 (16C, Bn-C); 128.66 (16C, Bn-C); 127.57 (2C, Ar-C); 126.03 (8C, Bn-C); 125.64 (4C, Ar-C); 123.96 (2C, Ar-C); 45.72 (2C, -N-CH2-); 39.61 (8C, 1J119Sn-13C = 728 Hz, 2J119Sn-13C = 29 Hz, 3J119Sn-13C = 65 Hz, Bn-C: -CH2-). 119Sn NMR (CDCl3, ppm): -97, -121.
  • 56
  • [ 51411-04-2 ]
  • [ 2273-51-0 ]
  • C40H26N2O8Sn [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In benzene; for 8h;Reflux; Dean-Stark; General procedure: To a suspension of Bn2SnO (0.634 g, 2 mmol) in benzene (30 mL), HL (0.255 g, 1 mmol) was added. The mixture was stirred and heated under reflux for 8 h in a Dean-Stark apparatus for azeotropic removal of the water formed in the reaction. After filtering, clear solution was obtained. The filter liquor was evaporated in vacuum to give colorless crystals of complex 1. Yield: 70%
  • 57
  • [ 51411-04-2 ]
  • [ 818-08-6 ]
  • C36H32N2O8Sn [ No CAS ]
  • 58
  • [ 51411-04-2 ]
  • [carbonato(at)silverI2041111-tert-butylthiolato)10(nitrato)8(N,N-dimethylacetamide)4] [ No CAS ]
  • [ 75-05-8 ]
  • [CO3(at)AgI2041111-StBu)10(C12H6O2NCH2COO)8]*4CH3CN [ No CAS ]
  • 59
  • [ 29022-11-5 ]
  • [ 51411-04-2 ]
  • [ 35661-40-6 ]
  • [ 71989-14-5 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • C35H38N8O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.29 g General procedure: Embodiments of grafting four amino acids is begun with swelling 2-chlorotrityl chloride resin (1.2 g, 1 mmol) in anhydrous dichloromethane (CH2Cl2) for 30 min, and a first amino acid having a Fmoc protective group is dissolved in anhydrous DMF and DIEA (0.83 ml, 5.0 mmol). Then, the first amino acid is reacted with the 2-chlorotrityl chloride resin for 1 hour to graft the first amino acid on the 2-chlorotrityl chloride resin. After that, piperidine (20% in DMF) is added and reacted for 20 minutes to remove the Fmoc protective group on the first amino acid, and the above step is repeated twice (2 minutes each time). (0218) Subsequently, a second amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin for 30 minutes. During the reaction, the HBTU acts as a coupling agent to make the second amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the first amino acid. Then, piperidine (20% in DMF) is again added and reacted for 20 minutes, and the above step is repeated twice (2 minutes each time) to remove the Fmoc protective group on the second amino acid. (0219) Subsequently, a third amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin for 30 minutes. During the reaction, the HBTU acts as the coupling agent to make the third amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the second amino acid. In order to remove the Fmoc protective group on the third amino acid, piperidine (20% in DMF) is added and reacted for 20 minutes, and the above step is repeated twice (2 minutes each time). (0220) Then, a fourth amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin for 30 minutes. During the reaction, the HBTU acts as the coupling agent to make the fourth amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the third amino acid. As the same step mentioned above, the Fmoc protective group on the fourth amino acid is removed by adding piperidine (20% in DMF) to react for 20 minutes, and the above step is repeated twice (2 minutes each time). (0221) After that, the terminal luminophore, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as the coupling agent to make the terminal luminophore couple to a free amino group (the Fmoc protective group thereon is removed) of the fourth amino acid. (0222) The reaction mixture is stirred overnight, and then the water-soluble peptide fluorescence material is cleaved from the 2-chlorotrityl chloride resin through treatment of trifluoroacetic acid (90% in deionized water) for 3 hours. The resulting solution is further dried under a stream of air, and diethyl ether is added to precipitate a target product. Then, the precipitate is dried under vacuum to remove residual solvent, and the remained solid product is the water-soluble peptide fluorescence material, which is under structure analysis by a nuclear magnetic resonance (1H NMR and 13C NMR). Continuing in Table 5, which shows different water-soluble peptide fluorescence materials synthesized from four amino acids and various terminal luminophores. [table-us-00005-en] TABLE 5 Different water-soluble peptide fluorescence materials synthesized from four amino acids and various terminal luminophores. second third fourth first amino amino amino amino terminal structure of acid acid acid acid luminophore the product (weight, (weight, (weight, (weight, (weight, (color, Embodiment mol) mol) mol) mol) mol) weight) Embodiment Fmoc-O-tert- Fmoc-L- Fmoc-L- Fmoc-L- NI III-24 24 butyl-L- glycine glycine glycine (0.77 g, (white tyrosine (0.6 g, (0.6 g, (0.6 g, 3.0 mmol) solid, (0.92 g, 2.0 mmol) 2.0 mmol) 2.0 mmol) 0.42 g) 2.0 mmol) Embodiment Fmoc-O-tert- Fmoc-L- Fmoc-Pbf- Fmoc-L- NI III-25 25 butyl-L- glycine L-arginine phenylalanine (0.51 g, (white aspartic (0.6 g, (1.3 g, (0.78 g, 2.0 mmol) solid, acid 2.0 mmol) 2.0 mmol) 2.0 mmol) 0.29 g) (0.92 g, 2.0 mmol) Embodiment Fmoc-L-aspartic Fmoc-L-aspartic Fmoc-L-aspartic Fmoc-L- PPNI III-26 26 acid acid acid phenylalanine (0.677 g, (brown (0.62 g, (0.62 g, (0.62 g, (0.58 g, 2.0 mmol) solid, 1.5 mmol) 1.5 mmol) 1.5 mmol) 1.5 mmol) 0.734 g) Embodiment Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- PPNI III-27 27 glutamic glutamic glutamic phenylalanine (0.4365 g, (yellow acid acid acid (0.387 g, 1.0 mmol) solid, (0.425 g, (0.425 g, (0.425 g, 1.0 mmol) 0.350 g) 1.0 mmol) 1.0 mmol) 1.0 mmol)
  • 60
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 51411-04-2 ]
  • [ 35661-40-6 ]
  • Fmoc-Glu(*)-OH [ No CAS ]
  • Fmoc-Asp(*)-OH [ No CAS ]
  • C37H38N6O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.05 g General procedure: Refer to embodiments of grafting four amino acids mentioned in 2-4 to understand embodiments of grafting five amino acids. Before grafting the terminal luminophore, a step of grafting a fifth amino acid is performed in a way the same as grafting the fourth amino acid, and the details are not described herein. The product is also under structure analysis by a nuclear magnetic resonance (1H NMR and 13C NMR). Continuing in Table 6, which shows different water-soluble peptide fluorescence materials synthesized from five amino acids and various terminal luminophores. [table-us-00006-en] TABLE 6 Different water-soluble peptide fluorescence materials synthesized from five amino acids and various terminal luminophores. first second third fourth fifth structure amino amino amino amino amino terminal of the acid acid acid acid acid luminophore product (weight, (weight, (weight, (weight, (weight, (weight, (color, Embodiment mol) mol) mol) mol) mol) mol) weight) Embodiment Fmoc-L-alanine Fmoc-L-glutamic Fmoc-L-glycine Fmoc-L-aspartic Fmoc-L- NI III-28 28 (0.623 g, acid (0.6 g, acid phenylalanine (0.77 g, (white 2.0 mmol) (0.851 g, 2.0 mmol) (0.823 g, (0.78 g, 2.0 mmol) 3.0 mmol) solid, 2.0 mmol) 2.0 mmol) 0.05 g) Embodiment Fmoc-L-alanine Fmoc-L-glutamic Fmoc-L-glycine Fmoc-L-aspartic Fmoc-L- PPNI III-29 29 (0.623 g, acid (0.6 g, acid phenylalanine (1.02 g, (yellow 2.0 mmol) (0.851 g, 2.0 mmol) (0.823 g, (0.78 g, 2.0 mmol) 3.0 mmol) solid, 2.0 mmol) 2.0 mmol) 0.6956 g) (0246) The product of Embodiment 28 has a structure of formula including a peptide sequence Phe-Asp-Gly-Glu-Ala (SEQ ID NO: 5) (III-28): (0247) The NMR spectroscopy of the product in Embodiment 28 is shown below: (0248) 1H NMR (300 MHz, DMSO-d6): delta=1.29 (d, J(H, H)=7.2 Hz, 3H; CH3), 1.70-1.90 (m, 1H; CH2), 1.85-2.05 (m, 1H; CH2), 2.29 (t, J(H, H)=8.25 Hz, 2H; CH2), 2.70-2.90 (m, 2H; CH2), 3.00-3.15 (m, 1H; CH2), 3.65-3.85 (m, 2H; CH2), 4.15-4.30 (m, 1H; CH), 4.30-4.40 (m, 1H; CH), 4.50-4.65 (m, 2H; CH), 4.78 (s, 2H; CH2), 7.20-7.30 (m, 5H; CH), 7.93 (t, J(H, H)=7.8 Hz, 4H; CH), 8.29 (d, J(H,H)=7.2 Hz, 1H; NH), 8.40-8.65 (m, 6H; NH, CH); (0249) 13C NMR (75 MHz, DMSO-d6): delta=17.8, 28.5, 30.9, 36.9, 38.4, 43.1, 48.4, 50.6, 52.4, 54.9, 122.8, 127.2, 128.2, 128.4, 129.0, 130.2, 131.8, 132.3, 135.5, 138.5, 164.2, 167.6, 169.2, 171.6, 171.7, 172.0, 172.7, 174.8, 175.0; (0250) MS [ESI-]: m/z (%): expected value: 774.25, experimental value: 773.3 [M-H-].
  • 61
  • [ 68858-20-8 ]
  • [ 35661-39-3 ]
  • [ 51411-04-2 ]
  • [ 35661-40-6 ]
  • [ 71989-23-6 ]
  • Fmoc-Lys(*)-OH [ No CAS ]
  • C48H64N8O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.92 g General procedure: Refer to embodiments of grafting four amino acids mentioned in 2-4 to understand embodiments of grafting six amino acids. Before grafting the terminal luminophore, a step of grafting a fifth amino acid and a sixth amino acid is performed in a way the same as grafting the fourth amino acid, and the details are not described herein. The product is also under structure analysis by a nuclear magnetic resonance (1H NMR and 13C NMR). Continuing in Table 7, which shows different water-soluble peptide fluorescence materials synthesized from five amino acids and various terminal luminophores. [table-us-00007-en] TABLE 7 Different water-soluble peptide fluorescence materials synthesized from six amino acids and various terminal luminophores first second third fourth fifth sixth structure amino amino amino amino amino amino terminal of the acid acid acid acid acid acid luminophore product (weight, (weight, (weight, (weight, (weight, (weight, (weight, (color, Embodiment mol) mol) mol) mol) mol) mol) mol) weight) Embodiment Fmoc- Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- NI III-30 30 O-tert- glycine glycine glycine glycine glycine (0.51 g, (white butyl-L- (0.6 g, (0.6 g, (0.6 g, (0.6 g, (0.6 g, 2.0 mmol) solid, tyrosine 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 0.20 g) (0.92 g, 2.0 mmol) Embodiment Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- NI III-31 31 valine alanine valine lysine isolucine phenylalanine (0.79 g, (white (0.68 g, (0.622 g, (0.68 g, (0.94 g, (0.71 g, (0.78 g, 3.0 mmol) solid, 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 0.92 g)
  • 62
  • [ 51411-04-2 ]
  • [ 35661-40-6 ]
  • C23H18N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.14 g General procedure: After the synthesis of the terminal luminophore, a solid phase peptide synthesis (SPPS) is applied to prepare the water-soluble peptide fluorescence material using 2-chlorotrityl chloride resin, amino acid and the terminal luminophore. (0082) The amino acid is grafted to the terminal luminophore by following steps. The 2-chlorotrityl chloride resin (1.2 g, 1 mmol) is swelled in anhydrous dichloromethane (CH2Cl2) for 30 min, and a first amino acid having a Fmoc protective group is dissolved in anhydrous N, N-dimethylformamide (DMF) and N, N-diisopropylethylamine (DIEA, 0.83 ml, 5.0 mmol). Then, the first amino acid is reacted with the 2-chlorotrityl chloride resin for 1 hour to graft the first amino acid on the 2-chlorotrityl chloride resin. (0083) After that, piperidine (20% in DMF) is added and reacted for 35 minutes to remove the Fmoc protective group on the first amino acid, and the above step is repeated twice (2 minutes each time). Subsequently, the terminal luminophore, DIEA (0.83 ml, 5.0 mmol) and O-(benzotriazol-1-yl)-N,N,N?,N?-tetramethyluraniumhexafluorophosphate (HBTU, 0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as a coupling agent to make the terminal luminophore couple to a free amino group (the Fmoc protective group thereon is removed) of the first amino acid. (0084) The reaction mixture is stirred overnight, and then the water-soluble peptide fluorescence material is cleaved from the 2-chlorotrityl chloride resin through treatment of trifluoroacetic acid (90% in deionized water) for 3 hours. The resulting solution is further dried under a stream of air, and diethyl ether is added to precipitate a target product. Then, the precipitate is dried under vacuum to remove residual solvent, and the remained solid product is the water-soluble peptide fluorescence material. Continuing in Table 2, which shows different water-soluble peptide fluorescence materials synthesized from various amino acids and terminal luminophores. [table-us-00002-en] TABLE 2 Different water-soluble peptide fluorescence materials synthesized from various amino acids and terminal luminophores. terminal structure of the first amino acid luminophore product Embodiment (weight, mol) (weight, mol) (color, weight) Embodiment 1 Fmoc-L-phenylalanine NI III-1 (0.78 g, 2.0 mmol) (0.51 g, 2 mmol) (white solid, 0.14 g) Embodiment 2 Fmoc-O-tert-butyl-L-tyrosine NI III-2 (0.92 g, 2.0 mmol) (0.77 g, 3 mmol) (white solid, 0.14 g) Embodiment 3 Fmoc-L-glycine NI III-3 (0.59 g, 2.0 mmol) (0.77 g, 3 mmol) (white solid, 0.17 g) Embodiment 4 Fmoc-L-phenylalanine PPNI III-4 (0.78 g, 2.0 mmol) (1.02 g, 3 mmol) (white solid, 0.18 g) (0085) The product of Embodiment 1 has a structure of formula (III-1): (0086) The NMR spectroscopy of the product in Embodiment 1 is shown below: (0087) 1H NMR (300 MHz, DMSO-d6): delta=2.90-3.15 (m, 2H, CH2), 4.40-4.50 (m, 1H, CH), 4.73 (s, 2H, CH2), 7.20-7.40 (m, 5H, CH), 7.94 (t, 2H, CH), 8.50-8.60 (m, 4H, CH), 8.63 (d, 1H, NH); (0088) 13C NMR (75 MHz, DMSO-d6): delta=38.1, 43.1, 54.9, 122.9, 127.3, 128.2, 128.4, 129.1, 130.2, 131.8, 132.3, 135.5, 135.7, 138.6, 164.1, 167.4; (0089) MS [ESI-]: m/z (%): expected value: 402.12, experimental value: 401.0 [M-H-].
  • 63
  • [ 51411-04-2 ]
  • [ 35661-40-6 ]
  • Fmoc-Tyr(*)-OH [ No CAS ]
  • C32H27N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.06 g General procedure: Embodiments of grafting two amino acids is begun with swelling 2-chlorotrityl chloride resin (1.2 g, 1 mmol) in anhydrous dichloromethane (CH2Cl2) for 30 min, and a first amino acid having a Fmoc protective group is dissolved in anhydrous DMF and DIEA (0.83 ml, 5.0 mmol). Then, the first amino acid is reacted with the 2-chlorotrityl chloride resin for 1 hour to graft the first amino acid on the 2-chlorotrityl chloride resin. After that, piperidine (20% in DMF) is added and reacted for 35 minutes to remove the Fmoc protective group on the first amino acid, and the above step is repeated twice (2 minutes each time). Subsequently, a second amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as a coupling agent to make the second amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the first amino acid. (0108) Then, piperidine (20% in DMF) is again added and reacted for 20 minutes, and the above step is repeated twice (2 minutes each time) to remove Fmoc protective group on the second amino acid. Subsequently, the terminal luminophore, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as the coupling agent to make the terminal luminophore couple to a free amino group (the Fmoc protective group thereon is removed) of the second amino acid. (0109) The reaction mixture is stirred overnight, and then the water-soluble peptide fluorescence material is cleaved from the 2-chlorotrityl chloride resin through treatment of trifluoroacetic acid (90% in deionized water) for 3 hours. The resulting solution is further dried under a stream of air, and diethyl ether is added to precipitate a target product. Then, the precipitate is dried under vacuum to remove residual solvent, and the remained solid product is the water-soluble peptide fluorescence material, which is under structure analysis by a nuclear magnetic resonance (1H NMR and 13C NMR). Continuing in Table 3, which shows different water-soluble peptide fluorescence materials synthesized from two amino acids and various terminal luminophores. [table-us-00003-en] TABLE 3 Different water-soluble peptide fluorescence materials synthesized from two amino acids and various terminal luminophores. structure terminal of the luminophore product first amino acid second amino acid (weight, (color, Embodiment (weight, mol) (weight, mol) mol) weight) Embodiment 5 Fmoc-L- Fmoc-L- NI III-5 glycine glycine (0.51 g, (white (0.59 g, (0.59 g, 2.0 mmol) 2.0 mmol) solid, 2.0 mmol) 0.35 g) Embodiment 6 Fmoc-L- Fmoc-L- NI III-6 phenylalanine phenylalanine (1.53 g, (white (1.16 g, (1.55 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.35 g) Embodiment 7 Fmoc-L- Fmoc-L- NI III-7 phenylalanine tyrosine (1.53 g, (white (1.16 g, 3.0 mmol)) (1.84 g, 4.0 mmol) 6.0 mmol) solid, 1.06 g) Embodiment 8 Fmoc-L- Fmoc-L- NI III-8 tyrosine phenylalanine (1.53 g, (white (1.38 g, 3.0 mmol)) (1.55 g, 4.0 mmol) 6.0 mmol) solid, 1.15 g) Embodiment 9 Fmoc-L- Fmoc-L- NI III-9 tyrosine tyrosine (0.51 g, (pale (0.919 g, 2.0 mmol)) (0.919 g, 2.0 mmol) 2.0 mmol) yellow solid, 0.32 g) Embodiment Fmoc-L- Fmoc-L- NI III-10 10 phenylalanine glycine (1.53 g, (white (1.16 g, (1.19 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.48 g) Embodiment Fmoc-L- Fmoc-L- NI III-11 11 glycine phenylalanine (1.53 g, (white (0.89 g, (1.55 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.38 g) Embodiment Fmoc-L- Fmoc-O-tert- NI III-12 12 glycine butyl-L-tyrosine (0.35 g, (white (0.4 g, (0.61 g, 1.3 mmol) 1.3 mmol) solid, 1.3 mmol) 0.22 g) Embodiment Fmoc-O-tert- Fmoc-L- NI III-13 13 butyl-L-tyrosine glycine (0.77 g, (white (0.92 g, (0.6 g, 2.0 mmol) 3.0 mmol) solid, 2.0 mmol) 0.18 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-14 14 phenylalanine phenylalanine (0.51 g, (yellow (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.515 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-15 15 phenylalanine tyrosine (0.51 g, (yellow (0.58 g, (0.69 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.534 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-16 16 aspartic acid aspartic acid (0.677 g, (dark (0.62 g, (0.62 g, 1.5 mmol) 2.0 mmol) brown 1.5 mmol) solid, 0.376 g) Embodiment Fmoc-L- Fmoc-L-phenylalanine PPNI III-17 17 aspartic acid (0.58 g, 1.5 mmol) (0.677 g, (yellow (0.62 g, 2.0 mmol) solid, 1.5 mmol) 0.554 g) Embodiment Fmoc-L- Fmoc-L- PRNI III-18 18 phenylalanine phenylalanine (0.486 g, (orange (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.434 g) Embodiment Fmoc-L- Fmoc-L- AHNI III-19 19 phenylalanine phenylalanine (0.528 g, (yellow (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.611 g) Embodiment Fmoc-L- Fmoc-L- AONI III-20 20 phenylalanine phenylalanine (0.366 g, (yellow (0.29 g, (0.29 g, 0.75 mmol) 1 mmol) solid, 0.75 mmol) 0.248 g) Em...
  • 64
  • [ 29022-11-5 ]
  • [ 51411-04-2 ]
  • [ 71989-38-3 ]
  • C25H21N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.22 g General procedure: Embodiments of grafting two amino acids is begun with swelling 2-chlorotrityl chloride resin (1.2 g, 1 mmol) in anhydrous dichloromethane (CH2Cl2) for 30 min, and a first amino acid having a Fmoc protective group is dissolved in anhydrous DMF and DIEA (0.83 ml, 5.0 mmol). Then, the first amino acid is reacted with the 2-chlorotrityl chloride resin for 1 hour to graft the first amino acid on the 2-chlorotrityl chloride resin. After that, piperidine (20% in DMF) is added and reacted for 35 minutes to remove the Fmoc protective group on the first amino acid, and the above step is repeated twice (2 minutes each time). Subsequently, a second amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as a coupling agent to make the second amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the first amino acid. (0108) Then, piperidine (20% in DMF) is again added and reacted for 20 minutes, and the above step is repeated twice (2 minutes each time) to remove Fmoc protective group on the second amino acid. Subsequently, the terminal luminophore, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as the coupling agent to make the terminal luminophore couple to a free amino group (the Fmoc protective group thereon is removed) of the second amino acid. (0109) The reaction mixture is stirred overnight, and then the water-soluble peptide fluorescence material is cleaved from the 2-chlorotrityl chloride resin through treatment of trifluoroacetic acid (90% in deionized water) for 3 hours. The resulting solution is further dried under a stream of air, and diethyl ether is added to precipitate a target product. Then, the precipitate is dried under vacuum to remove residual solvent, and the remained solid product is the water-soluble peptide fluorescence material, which is under structure analysis by a nuclear magnetic resonance (1H NMR and 13C NMR). Continuing in Table 3, which shows different water-soluble peptide fluorescence materials synthesized from two amino acids and various terminal luminophores. [table-us-00003-en] TABLE 3 Different water-soluble peptide fluorescence materials synthesized from two amino acids and various terminal luminophores. structure terminal of the luminophore product first amino acid second amino acid (weight, (color, Embodiment (weight, mol) (weight, mol) mol) weight) Embodiment 5 Fmoc-L- Fmoc-L- NI III-5 glycine glycine (0.51 g, (white (0.59 g, (0.59 g, 2.0 mmol) 2.0 mmol) solid, 2.0 mmol) 0.35 g) Embodiment 6 Fmoc-L- Fmoc-L- NI III-6 phenylalanine phenylalanine (1.53 g, (white (1.16 g, (1.55 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.35 g) Embodiment 7 Fmoc-L- Fmoc-L- NI III-7 phenylalanine tyrosine (1.53 g, (white (1.16 g, 3.0 mmol)) (1.84 g, 4.0 mmol) 6.0 mmol) solid, 1.06 g) Embodiment 8 Fmoc-L- Fmoc-L- NI III-8 tyrosine phenylalanine (1.53 g, (white (1.38 g, 3.0 mmol)) (1.55 g, 4.0 mmol) 6.0 mmol) solid, 1.15 g) Embodiment 9 Fmoc-L- Fmoc-L- NI III-9 tyrosine tyrosine (0.51 g, (pale (0.919 g, 2.0 mmol)) (0.919 g, 2.0 mmol) 2.0 mmol) yellow solid, 0.32 g) Embodiment Fmoc-L- Fmoc-L- NI III-10 10 phenylalanine glycine (1.53 g, (white (1.16 g, (1.19 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.48 g) Embodiment Fmoc-L- Fmoc-L- NI III-11 11 glycine phenylalanine (1.53 g, (white (0.89 g, (1.55 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.38 g) Embodiment Fmoc-L- Fmoc-O-tert- NI III-12 12 glycine butyl-L-tyrosine (0.35 g, (white (0.4 g, (0.61 g, 1.3 mmol) 1.3 mmol) solid, 1.3 mmol) 0.22 g) Embodiment Fmoc-O-tert- Fmoc-L- NI III-13 13 butyl-L-tyrosine glycine (0.77 g, (white (0.92 g, (0.6 g, 2.0 mmol) 3.0 mmol) solid, 2.0 mmol) 0.18 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-14 14 phenylalanine phenylalanine (0.51 g, (yellow (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.515 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-15 15 phenylalanine tyrosine (0.51 g, (yellow (0.58 g, (0.69 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.534 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-16 16 aspartic acid aspartic acid (0.677 g, (dark (0.62 g, (0.62 g, 1.5 mmol) 2.0 mmol) brown 1.5 mmol) solid, 0.376 g) Embodiment Fmoc-L- Fmoc-L-phenylalanine PPNI III-17 17 aspartic acid (0.58 g, 1.5 mmol) (0.677 g, (yellow (0.62 g, 2.0 mmol) solid, 1.5 mmol) 0.554 g) Embodiment Fmoc-L- Fmoc-L- PRNI III-18 18 phenylalanine phenylalanine (0.486 g, (orange (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.434 g) Embodiment Fmoc-L- Fmoc-L- AHNI III-19 19 phenylalanine phenylalanine (0.528 g, (yellow (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.611 g) Embodiment Fmoc-L- Fmoc-L- AONI III-20 20 phenylalanine phenylalanine (0.366 g, (yellow (0.29 g, (0.29 g, 0.75 mmol) 1 mmol) solid, 0.75 mmol) 0.248 g) Em...
  • 65
  • [ 29022-11-5 ]
  • [ 51411-04-2 ]
  • [ 71989-38-3 ]
  • C29H27N5O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.42 g General procedure: Embodiments of grafting four amino acids is begun with swelling 2-chlorotrityl chloride resin (1.2 g, 1 mmol) in anhydrous dichloromethane (CH2Cl2) for 30 min, and a first amino acid having a Fmoc protective group is dissolved in anhydrous DMF and DIEA (0.83 ml, 5.0 mmol). Then, the first amino acid is reacted with the 2-chlorotrityl chloride resin for 1 hour to graft the first amino acid on the 2-chlorotrityl chloride resin. After that, piperidine (20% in DMF) is added and reacted for 20 minutes to remove the Fmoc protective group on the first amino acid, and the above step is repeated twice (2 minutes each time). (0218) Subsequently, a second amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin for 30 minutes. During the reaction, the HBTU acts as a coupling agent to make the second amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the first amino acid. Then, piperidine (20% in DMF) is again added and reacted for 20 minutes, and the above step is repeated twice (2 minutes each time) to remove the Fmoc protective group on the second amino acid. (0219) Subsequently, a third amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin for 30 minutes. During the reaction, the HBTU acts as the coupling agent to make the third amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the second amino acid. In order to remove the Fmoc protective group on the third amino acid, piperidine (20% in DMF) is added and reacted for 20 minutes, and the above step is repeated twice (2 minutes each time). (0220) Then, a fourth amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin for 30 minutes. During the reaction, the HBTU acts as the coupling agent to make the fourth amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the third amino acid. As the same step mentioned above, the Fmoc protective group on the fourth amino acid is removed by adding piperidine (20% in DMF) to react for 20 minutes, and the above step is repeated twice (2 minutes each time). (0221) After that, the terminal luminophore, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as the coupling agent to make the terminal luminophore couple to a free amino group (the Fmoc protective group thereon is removed) of the fourth amino acid. (0222) The reaction mixture is stirred overnight, and then the water-soluble peptide fluorescence material is cleaved from the 2-chlorotrityl chloride resin through treatment of trifluoroacetic acid (90% in deionized water) for 3 hours. The resulting solution is further dried under a stream of air, and diethyl ether is added to precipitate a target product. Then, the precipitate is dried under vacuum to remove residual solvent, and the remained solid product is the water-soluble peptide fluorescence material, which is under structure analysis by a nuclear magnetic resonance (1H NMR and 13C NMR). Continuing in Table 5, which shows different water-soluble peptide fluorescence materials synthesized from four amino acids and various terminal luminophores. [table-us-00005-en] TABLE 5 Different water-soluble peptide fluorescence materials synthesized from four amino acids and various terminal luminophores. second third fourth first amino amino amino amino terminal structure of acid acid acid acid luminophore the product (weight, (weight, (weight, (weight, (weight, (color, Embodiment mol) mol) mol) mol) mol) weight) Embodiment Fmoc-O-tert- Fmoc-L- Fmoc-L- Fmoc-L- NI III-24 24 butyl-L- glycine glycine glycine (0.77 g, (white tyrosine (0.6 g, (0.6 g, (0.6 g, 3.0 mmol) solid, (0.92 g, 2.0 mmol) 2.0 mmol) 2.0 mmol) 0.42 g) 2.0 mmol) Embodiment Fmoc-O-tert- Fmoc-L- Fmoc-Pbf- Fmoc-L- NI III-25 25 butyl-L- glycine L-arginine phenylalanine (0.51 g, (white aspartic (0.6 g, (1.3 g, (0.78 g, 2.0 mmol) solid, acid 2.0 mmol) 2.0 mmol) 2.0 mmol) 0.29 g) (0.92 g, 2.0 mmol) Embodiment Fmoc-L-aspartic Fmoc-L-aspartic Fmoc-L-aspartic Fmoc-L- PPNI III-26 26 acid acid acid phenylalanine (0.677 g, (brown (0.62 g, (0.62 g, (0.62 g, (0.58 g, 2.0 mmol) solid, 1.5 mmol) 1.5 mmol) 1.5 mmol) 1.5 mmol) 0.734 g) Embodiment Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- PPNI III-27 27 glutamic glutamic glutamic phenylalanine (0.4365 g, (yellow acid acid acid (0.387 g, 1.0 mmol) solid, (0.425 g, (0.425 g, (0.425 g, 1.0 mmol) 0.350 g) 1.0 mmol) 1.0 mmol) 1.0 mmol) (0223) The product of Embodiment 24 has a structure of formula including a peptide sequence Gly-Gly-Gly-Tyr (SEQ ...
  • 66
  • [ 29022-11-5 ]
  • [ 51411-04-2 ]
  • [ 71989-38-3 ]
  • C33H33N7O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.20 g General procedure: Refer to embodiments of grafting four amino acids mentioned in 2-4 to understand embodiments of grafting six amino acids. Before grafting the terminal luminophore, a step of grafting a fifth amino acid and a sixth amino acid is performed in a way the same as grafting the fourth amino acid, and the details are not described herein. The product is also under structure analysis by a nuclear magnetic resonance (1H NMR and 13C NMR). Continuing in Table 7, which shows different water-soluble peptide fluorescence materials synthesized from five amino acids and various terminal luminophores. [table-us-00007-en] TABLE 7 Different water-soluble peptide fluorescence materials synthesized from six amino acids and various terminal luminophores first second third fourth fifth sixth structure amino amino amino amino amino amino terminal of the acid acid acid acid acid acid luminophore product (weight, (weight, (weight, (weight, (weight, (weight, (weight, (color, Embodiment mol) mol) mol) mol) mol) mol) mol) weight) Embodiment Fmoc- Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- NI III-30 30 O-tert- glycine glycine glycine glycine glycine (0.51 g, (white butyl-L- (0.6 g, (0.6 g, (0.6 g, (0.6 g, (0.6 g, 2.0 mmol) solid, tyrosine 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 0.20 g) (0.92 g, 2.0 mmol) Embodiment Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- Fmoc-L- NI III-31 31 valine alanine valine lysine isolucine phenylalanine (0.79 g, (white (0.68 g, (0.622 g, (0.68 g, (0.94 g, (0.71 g, (0.78 g, 3.0 mmol) solid, 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 2.0 mmol) 0.92 g) (0260) The product of Embodiment 30 has a structure of formula including a peptide sequence Gly-Gly-Gly-Gly-Gly-Tyr (SEQ ID NO: 7) (III-30): (0261) The NMR spectroscopy of the product in Embodiment 30 is shown below: (0262) 1H NMR (300 MHz, DMSO-d6): delta=2.70-3.05 (m, 2H; CH2), 3.60-3.90 (m, 10H; CH2), 4.30-4.40 (m, 1H; CH), 4.70-4.80 (m, 2H; CH2), 6.68 (d, J=8.4 Hz, 2H; CH), 7.03 (d, J=8.4 Hz, 2H; CH), 7.94 (t, J=7.8 Hz, 2H; CH), 8.00-8.10 (m, 2H; NH), 8.10-8.25 (m, 3H; NH), 8.50-8.65 (m, 4H; CH); (0263) 13C NMR (75 MHz, DMSO-d6): delta=37.0, 42.2, 42.5, 43.0, 43.3, 54.8, 116.0, 122.9, 128.2, 128.3, 128.4, 128.5, 131.0, 131.8, 135.5, 156.9, 164.3, 168.2, 169.5, 169.9, 170.07, 170.13, 170.3, 173.9; (0264) MS [ESI-]: m/z (%): expected value: 703.22, experimental value: 702.0[M-H]-.
  • 67
  • [ 29022-11-5 ]
  • [ 51411-04-2 ]
  • C18H15N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.35 g General procedure: Embodiments of grafting two amino acids is begun with swelling 2-chlorotrityl chloride resin (1.2 g, 1 mmol) in anhydrous dichloromethane (CH2Cl2) for 30 min, and a first amino acid having a Fmoc protective group is dissolved in anhydrous DMF and DIEA (0.83 ml, 5.0 mmol). Then, the first amino acid is reacted with the 2-chlorotrityl chloride resin for 1 hour to graft the first amino acid on the 2-chlorotrityl chloride resin. After that, piperidine (20% in DMF) is added and reacted for 35 minutes to remove the Fmoc protective group on the first amino acid, and the above step is repeated twice (2 minutes each time). Subsequently, a second amino acid having a Fmoc protective group, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as a coupling agent to make the second amino acid couple to a free amino group (the Fmoc protective group thereon is removed) of the first amino acid. (0108) Then, piperidine (20% in DMF) is again added and reacted for 20 minutes, and the above step is repeated twice (2 minutes each time) to remove Fmoc protective group on the second amino acid. Subsequently, the terminal luminophore, DIEA (0.83 ml, 5.0 mmol) and HBTU (0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as the coupling agent to make the terminal luminophore couple to a free amino group (the Fmoc protective group thereon is removed) of the second amino acid. (0109) The reaction mixture is stirred overnight, and then the water-soluble peptide fluorescence material is cleaved from the 2-chlorotrityl chloride resin through treatment of trifluoroacetic acid (90% in deionized water) for 3 hours. The resulting solution is further dried under a stream of air, and diethyl ether is added to precipitate a target product. Then, the precipitate is dried under vacuum to remove residual solvent, and the remained solid product is the water-soluble peptide fluorescence material, which is under structure analysis by a nuclear magnetic resonance (1H NMR and 13C NMR). Continuing in Table 3, which shows different water-soluble peptide fluorescence materials synthesized from two amino acids and various terminal luminophores. [table-us-00003-en] TABLE 3 Different water-soluble peptide fluorescence materials synthesized from two amino acids and various terminal luminophores. structure terminal of the luminophore product first amino acid second amino acid (weight, (color, Embodiment (weight, mol) (weight, mol) mol) weight) Embodiment 5 Fmoc-L- Fmoc-L- NI III-5 glycine glycine (0.51 g, (white (0.59 g, (0.59 g, 2.0 mmol) 2.0 mmol) solid, 2.0 mmol) 0.35 g) Embodiment 6 Fmoc-L- Fmoc-L- NI III-6 phenylalanine phenylalanine (1.53 g, (white (1.16 g, (1.55 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.35 g) Embodiment 7 Fmoc-L- Fmoc-L- NI III-7 phenylalanine tyrosine (1.53 g, (white (1.16 g, 3.0 mmol)) (1.84 g, 4.0 mmol) 6.0 mmol) solid, 1.06 g) Embodiment 8 Fmoc-L- Fmoc-L- NI III-8 tyrosine phenylalanine (1.53 g, (white (1.38 g, 3.0 mmol)) (1.55 g, 4.0 mmol) 6.0 mmol) solid, 1.15 g) Embodiment 9 Fmoc-L- Fmoc-L- NI III-9 tyrosine tyrosine (0.51 g, (pale (0.919 g, 2.0 mmol)) (0.919 g, 2.0 mmol) 2.0 mmol) yellow solid, 0.32 g) Embodiment Fmoc-L- Fmoc-L- NI III-10 10 phenylalanine glycine (1.53 g, (white (1.16 g, (1.19 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.48 g) Embodiment Fmoc-L- Fmoc-L- NI III-11 11 glycine phenylalanine (1.53 g, (white (0.89 g, (1.55 g, 4.0 mmol) 6.0 mmol) solid, 3.0 mmol) 0.38 g) Embodiment Fmoc-L- Fmoc-O-tert- NI III-12 12 glycine butyl-L-tyrosine (0.35 g, (white (0.4 g, (0.61 g, 1.3 mmol) 1.3 mmol) solid, 1.3 mmol) 0.22 g) Embodiment Fmoc-O-tert- Fmoc-L- NI III-13 13 butyl-L-tyrosine glycine (0.77 g, (white (0.92 g, (0.6 g, 2.0 mmol) 3.0 mmol) solid, 2.0 mmol) 0.18 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-14 14 phenylalanine phenylalanine (0.51 g, (yellow (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.515 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-15 15 phenylalanine tyrosine (0.51 g, (yellow (0.58 g, (0.69 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.534 g) Embodiment Fmoc-L- Fmoc-L- PPNI III-16 16 aspartic acid aspartic acid (0.677 g, (dark (0.62 g, (0.62 g, 1.5 mmol) 2.0 mmol) brown 1.5 mmol) solid, 0.376 g) Embodiment Fmoc-L- Fmoc-L-phenylalanine PPNI III-17 17 aspartic acid (0.58 g, 1.5 mmol) (0.677 g, (yellow (0.62 g, 2.0 mmol) solid, 1.5 mmol) 0.554 g) Embodiment Fmoc-L- Fmoc-L- PRNI III-18 18 phenylalanine phenylalanine (0.486 g, (orange (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.434 g) Embodiment Fmoc-L- Fmoc-L- AHNI III-19 19 phenylalanine phenylalanine (0.528 g, (yellow (0.58 g, (0.58 g, 1.5 mmol) 1.5 mmol) solid, 1.5 mmol) 0.611 g) Embodiment Fmoc-L- Fmoc-L- AONI III-20 20 phenylalanine phenylalanine (0.366 g, (yellow (0.29 g, (0.29 g, 0.75 mmol) 1 mmol) solid, 0.75 mmol) 0.248 g) Em...
  • 68
  • [ 51411-04-2 ]
  • [ 71989-38-3 ]
  • C23H18N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.14 g General procedure: After the synthesis of the terminal luminophore, a solid phase peptide synthesis (SPPS) is applied to prepare the water-soluble peptide fluorescence material using 2-chlorotrityl chloride resin, amino acid and the terminal luminophore. (0082) The amino acid is grafted to the terminal luminophore by following steps. The 2-chlorotrityl chloride resin (1.2 g, 1 mmol) is swelled in anhydrous dichloromethane (CH2Cl2) for 30 min, and a first amino acid having a Fmoc protective group is dissolved in anhydrous N, N-dimethylformamide (DMF) and N, N-diisopropylethylamine (DIEA, 0.83 ml, 5.0 mmol). Then, the first amino acid is reacted with the 2-chlorotrityl chloride resin for 1 hour to graft the first amino acid on the 2-chlorotrityl chloride resin. (0083) After that, piperidine (20% in DMF) is added and reacted for 35 minutes to remove the Fmoc protective group on the first amino acid, and the above step is repeated twice (2 minutes each time). Subsequently, the terminal luminophore, DIEA (0.83 ml, 5.0 mmol) and O-(benzotriazol-1-yl)-N,N,N?,N?-tetramethyluraniumhexafluorophosphate (HBTU, 0.76 g, 2.0 mmol) are dissolved in anhydrous DMF and reacted with the 2-chlorotrityl chloride resin. During the reaction, the HBTU acts as a coupling agent to make the terminal luminophore couple to a free amino group (the Fmoc protective group thereon is removed) of the first amino acid. (0084) The reaction mixture is stirred overnight, and then the water-soluble peptide fluorescence material is cleaved from the 2-chlorotrityl chloride resin through treatment of trifluoroacetic acid (90% in deionized water) for 3 hours. The resulting solution is further dried under a stream of air, and diethyl ether is added to precipitate a target product. Then, the precipitate is dried under vacuum to remove residual solvent, and the remained solid product is the water-soluble peptide fluorescence material. Continuing in Table 2, which shows different water-soluble peptide fluorescence materials synthesized from various amino acids and terminal luminophores. [table-us-00002-en] TABLE 2 Different water-soluble peptide fluorescence materials synthesized from various amino acids and terminal luminophores. terminal structure of the first amino acid luminophore product Embodiment (weight, mol) (weight, mol) (color, weight) Embodiment 1 Fmoc-L-phenylalanine NI III-1 (0.78 g, 2.0 mmol) (0.51 g, 2 mmol) (white solid, 0.14 g) Embodiment 2 Fmoc-O-tert-butyl-L-tyrosine NI III-2 (0.92 g, 2.0 mmol) (0.77 g, 3 mmol) (white solid, 0.14 g) Embodiment 3 Fmoc-L-glycine NI III-3 (0.59 g, 2.0 mmol) (0.77 g, 3 mmol) (white solid, 0.17 g) Embodiment 4 Fmoc-L-phenylalanine PPNI III-4 (0.78 g, 2.0 mmol) (1.02 g, 3 mmol) (white solid, 0.18 g)
  • 69
  • [ 51411-04-2 ]
  • C22H27N2O4Pol [ No CAS ]
  • C36H34N3O7Pol [ No CAS ]
  • 70
  • C22H27N2O4Pol [ No CAS ]
  • [ 51411-04-2 ]
  • C36H34N3O7Pol [ No CAS ]
  • 71
  • C26H35N2O5Pol [ No CAS ]
  • [ 51411-04-2 ]
  • C40H42N3O8Pol [ No CAS ]
  • 72
  • [ 51411-04-2 ]
  • C18H19N2O3Pol [ No CAS ]
  • C32H26N3O6Pol [ No CAS ]
  • 73
  • [ 1350284-65-9 ]
  • [ 51411-04-2 ]
  • C83H84N2O18 [ No CAS ]
  • 74
  • [ 51411-04-2 ]
  • [ 10424-65-4 ]
  • 1,8-naphthalimide-N-acetate tetramethylammonium salt [ No CAS ]
  • 75
  • [ 5407-57-8 ]
  • [ 51411-04-2 ]
  • N-(2-((7-chloroquinolin-4-yl)amino)ethyl)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; General procedure: The synthesis was initiated by heating 1,8-naphthalic anhydride 1,with glycine 5 in dry DMF at 100 C in the presence of triethyl amine asbase. The product obtained 6 (1 mmol) was then reacted with quinolinediamine 2 (1 mmol) using coupling reagents EDC (1.1 eq), HOBt(1.2 eq) and DIEA (2 eq) in anhydrous DMF for 1 h. The reaction wasmonitored using TLC and after its completion, water was added toquench the reaction. The desired products precipitated out of the reactionmixture which was filtered, washed with water and recrystallizedin ethanol to yield the desired conjugates.
  • 76
  • [ 7597-14-0 ]
  • [ 51411-04-2 ]
  • N-(3-((7-chloroquinolin-4-yl)amino)propyl)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; General procedure: The synthesis was initiated by heating 1,8-naphthalic anhydride 1,with glycine 5 in dry DMF at 100 C in the presence of triethyl amine asbase. The product obtained 6 (1 mmol) was then reacted with quinolinediamine 2 (1 mmol) using coupling reagents EDC (1.1 eq), HOBt(1.2 eq) and DIEA (2 eq) in anhydrous DMF for 1 h. The reaction wasmonitored using TLC and after its completion, water was added toquench the reaction. The desired products precipitated out of the reactionmixture which was filtered, washed with water and recrystallizedin ethanol to yield the desired conjugates.
  • 77
  • [ 51411-04-2 ]
  • [ 53186-45-1 ]
  • N-(4-((7-chloroquinolin-4-yl)amino)butyl)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; General procedure: The synthesis was initiated by heating 1,8-naphthalic anhydride 1,with glycine 5 in dry DMF at 100 C in the presence of triethyl amine asbase. The product obtained 6 (1 mmol) was then reacted with quinolinediamine 2 (1 mmol) using coupling reagents EDC (1.1 eq), HOBt(1.2 eq) and DIEA (2 eq) in anhydrous DMF for 1 h. The reaction wasmonitored using TLC and after its completion, water was added toquench the reaction. The desired products precipitated out of the reactionmixture which was filtered, washed with water and recrystallizedin ethanol to yield the desired conjugates.
  • 78
  • [ 104897-36-1 ]
  • [ 51411-04-2 ]
  • N-(6-((7-chloroquinolin-4-yl)amino)hexyl)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; General procedure: The synthesis was initiated by heating 1,8-naphthalic anhydride 1,with glycine 5 in dry DMF at 100 C in the presence of triethyl amine asbase. The product obtained 6 (1 mmol) was then reacted with quinolinediamine 2 (1 mmol) using coupling reagents EDC (1.1 eq), HOBt(1.2 eq) and DIEA (2 eq) in anhydrous DMF for 1 h. The reaction wasmonitored using TLC and after its completion, water was added toquench the reaction. The desired products precipitated out of the reactionmixture which was filtered, washed with water and recrystallizedin ethanol to yield the desired conjugates.
  • 79
  • [ 51411-04-2 ]
  • [ 1025956-25-5 ]
  • N-(8-((7-chloroquinolin-4-yl)amino)octyl)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; General procedure: The synthesis was initiated by heating 1,8-naphthalic anhydride 1,with glycine 5 in dry DMF at 100 C in the presence of triethyl amine asbase. The product obtained 6 (1 mmol) was then reacted with quinolinediamine 2 (1 mmol) using coupling reagents EDC (1.1 eq), HOBt(1.2 eq) and DIEA (2 eq) in anhydrous DMF for 1 h. The reaction wasmonitored using TLC and after its completion, water was added toquench the reaction. The desired products precipitated out of the reactionmixture which was filtered, washed with water and recrystallizedin ethanol to yield the desired conjugates.
  • 80
  • [ 51411-04-2 ]
  • [ 76-87-9 ]
  • C192H138N6O24Sn6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In toluene; for 8h;Reflux; Dean-Stark; The synthesis of complex 1 is shown in Scheme 3 . Triphenyltin hydroxide (0.367g, 1mmol) and HL (0.255g, 1mmol) were mixed together in 50mL of toluene. The mixture was heated under reflux for 8h with a Dean Stark apparatus for azeotropic removal of the water that was formed in the reaction. After reflux, the solution was filtered when the mixture had cooled to room temperature. The filtrate was retained and gradually evaporated. After four days, X-ray-quality colorless crystals were obtained. For complex 1, yield: 68%; Mp: 262.1-264.3C. Anal. Calcd. for C192H138N6O24Sn6: C, 63.61; N, 2.32; H, 3.81%. Found: C, 63.59; N, 2.38; H, 3.79%. IR (cm-1): v(O=C) 1721; vas(COO) 1600; vs(COO) 1411; v(Sn-C) 586; nu(Sn-O) 443. 1H NMR (CDCl3, ppm): delta 8.36 (d, 12H, J=7.3Hz, Ar-H); 8.29 (d, J=7.2Hz, 12H, Ar-H); 7.64 (dd, 12H, J=7.3Hz, Ar-H); 7.29 (t, 36H, J=7.1Hz, Ph-H); 7.20-7.24 (m, 54H, Ph-H); 4.56 (s, 12H, -CH2-). 1H NMR (DMSO-d6, ppm): delta 8.50 (d, 24H, J=7.2Hz, Ar-H); 7.89 (t, J=7.3Hz, 36H, Ph-H); 7.45 (dd, 12H, J=7.2Hz, Ar-H); 7.22-7.30 (m, 54H, Ph-H); 4.54 (s, 12H, -CH2-). 13C NMR (CDCl3, ppm): 175.49 (6C, COO); 163.64 (12C, C=O); 137.21 (12C, Ar-C: C10, C12); 136.67 (12C, Ar-C: C8, C14); 134.47 (18C, 1J119Sn-13C=718Hz, 2J119Sn-13C=20Hz, 3J119Sn-13C=64Hz, Ph-C: C15, C21, C27); 133.18 (36C, Ph-C: C17, C19, C23, C25, C29, C31); 132.67 (54C, Ph-C: C16, C18, C20, C22, C24, C26, C27, C29, C31); 130.84 (12C, Ar-C: C9, C13); 129.76 (6C, Ar-C: C11); 128.21 (12C, Ar-C: C4, C6); 124.85 (6C, Ar-C: C5); 37.24 (6C, -CH2-). 13C NMR (DMSO-d6, ppm): 170.42 (6C, COO); 163.60 (12C, C=O); 142.92 (12C, Ar-C: C10, C12); 137.81 (12C, Ar-C: C8, C14); 137.26 (18C, 1J119Sn-13C=726Hz, 2J119Sn-13C=23Hz, 3J119Sn-13C=67Hz, Ph-C: C15, C21, C27); 136.61 (54C, Ph-C: C16, C18, C20, C22, C24, C26, C27, C29, C31); 131.33 (12C, Ar-C: C9, C13); 129.79 (6C, Ar-C: C11); 128.51 (36C, Ph-C: C17, C19, C23, C25, C29, C31); 127.75 (12C, Ar-C: C4, C6); 122.37 (6C, Ar-C: C5); 43.26 (6C, -CH2-). 119Sn NMR (DMSO-d6, ppm): -107.54.
  • 81
  • [ 51411-04-2 ]
  • [ 147762-53-6 ]
  • C23H19N2O9P [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(fluorenylmethyloxycarbonyl)tyrosine-O-phosphate With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 1h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: alrestatin Further stages;
  • 82
  • [ 51411-04-2 ]
  • [ 35661-40-6 ]
  • [ 147762-53-6 ]
  • C32H28N3O10P [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(fluorenylmethyloxycarbonyl)tyrosine-O-phosphate With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 1h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: alrestatin; N-Fmoc L-Phe Further stages;
  • 83
  • [ 51411-04-2 ]
  • [ 140-88-5 ]
  • [ 150705-10-5 ]
YieldReaction ConditionsOperation in experiment
4% With Ir(dF(CF3)ppy)2(bpy)PF6; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Sealed tube; Inert atmosphere; Irradiation;
Same Skeleton Products
Historical Records

Similar Product of
[ 51411-04-2 ]

Chemical Structure| 51876-97-2

A890593[ 51876-97-2 ]

Sodium 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)acetate

Reason: Free-salt