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[ CAS No. 34535-98-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 34535-98-3
Chemical Structure| 34535-98-3
Chemical Structure| 34535-98-3
Structure of 34535-98-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 34535-98-3 ]

CAS No. :34535-98-3 MDL No. :MFCD04038984
Formula : C9H11N Boiling Point : -
Linear Structure Formula :- InChI Key :AOTWIFLKURJQGE-UHFFFAOYSA-N
M.W : 133.19 Pubchem ID :7016287
Synonyms :

Calculated chemistry of [ 34535-98-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.25
TPSA : 12.03 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) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 2.01
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 2.18
Consensus Log Po/w : 2.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.53
Solubility : 0.395 mg/ml ; 0.00297 mol/l
Class : Soluble
Log S (Ali) : -2.36
Solubility : 0.586 mg/ml ; 0.0044 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.129 mg/ml ; 0.000968 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 34535-98-3 ]

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

Application In Synthesis of [ 34535-98-3 ]

* 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 [ 34535-98-3 ]

[ 34535-98-3 ] Synthesis Path-Downstream   1~100

  • 2
  • [ 27374-25-0 ]
  • [ 62-53-3 ]
  • [ 34535-98-3 ]
  • Dicyclopropyl-phenyl-amine [ No CAS ]
  • 3
  • [ 598-21-0 ]
  • [ 34535-98-3 ]
  • [ 174180-98-4 ]
  • 4
  • [ 108-86-1 ]
  • [ 765-30-0 ]
  • [ 34535-98-3 ]
YieldReaction ConditionsOperation in experiment
58% With [Pd(allyl)(BrettPhos)]OTf; sodium t-butanolate; In toluene; at 90℃;Schlenk technique; Inert atmosphere; General procedure: The N-aryl aminocyclopropanes were synthesized according to the literature.[5] An oven-dried Schlenk tube equipped with a stirring bar was charged with [Pd(allyl)(brettphos)]OTf (0.025 mmol, 0.5 mol %), and NaOt-Bu (7.5 mmol). The tube was evacuated and backfilled with nitrogen for three times. The amine (7.5mmol), aryl bromine (5.0 mmol), and anhydrous toluene (40 mL) were added sequentially via syringe. The tube was placed in a preheated oil bath and the contents were stirred for the indicated time. The tube was then removed from the oil bath and allowed to cool to room temperature. The reaction mixture was diluted with 10 mL of dichloromethane and filtered through a pad of Celite. The solution was concentrated in vacuo, and the residue was purified on silica gel using n-hexane/ethyl acetate as eluent.
  • 5
  • [ 66715-65-9 ]
  • [ 34535-98-3 ]
  • N-phenyl-N-cyclopropylpyridine-2-sulfonamide [ No CAS ]
  • 6
  • N-phenyl-N-cyclopropylpyridine-2-sulfonamide [ No CAS ]
  • [ 34535-98-3 ]
  • 7
  • [ 34535-98-3 ]
  • [ 66223-76-5 ]
  • [ 400777-76-6 ]
  • 8
  • [ 34535-98-3 ]
  • [ 400777-76-6 ]
  • 9
  • [ 400777-68-6 ]
  • [ 34535-98-3 ]
  • 11
  • [ 725242-37-5 ]
  • [ 62-53-3 ]
  • [ 34535-98-3 ]
  • 12
  • [ 34535-98-3 ]
  • [ 168155-50-8 ]
  • 3-{(4-allyl-2,5-dimethyl-piperazin-1-yl)-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-phenyl]-methyl}-<i>N</i>-cyclopropyl-<i>N</i>-phenyl-benzamide [ No CAS ]
  • 13
  • [ 603-33-8 ]
  • [ 765-30-0 ]
  • [ 34535-98-3 ]
  • 14
  • [ 27374-25-0 ]
  • [ 62-53-3 ]
  • [ 34535-98-3 ]
  • 15
  • [ 34535-98-3 ]
  • [ 298-12-4 ]
  • [ 725242-37-5 ]
  • 16
  • [ 34535-98-3 ]
  • 3-((αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-cyclopropyl-N-phenylbenzamide [ No CAS ]
  • 17
  • [ 34535-98-3 ]
  • N-cyclopropyl-N-phenylglycine methyl ester [ No CAS ]
  • 18
  • [ 16350-99-5 ]
  • [ 34535-98-3 ]
  • 19
  • [ 34535-98-3 ]
  • [ 31121-11-6 ]
  • 20
  • [ 103-70-8 ]
  • [ 34535-98-3 ]
  • 21
  • [ 34535-98-3 ]
  • [ 174180-99-5 ]
  • 22
  • [ 34535-98-3 ]
  • N-Cyclopropyl-2-[3-(1H-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5,tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl-acetamide [ No CAS ]
  • 23
  • [ 34535-98-3 ]
  • [ 174180-97-3 ]
  • 24
  • [ 62-53-3 ]
  • p-toluenesulfonic acid-<p-amino-phenyl>-ester [ No CAS ]
  • [ 34535-98-3 ]
YieldReaction ConditionsOperation in experiment
Cyclopropylamine (1.0 g, 17.5 mmol.) was added to triphenylbismuth (9.25 g, 21.0 mmol.) and cupric acetate (1.6 g, 8.75 mmol) in dichloromethane (30 mL) at room temperature under nitrogen. The mixture was stirred for 18 hours, filtered over a short plug of celite to remove any insoluble material, and purified by chromatography on a silica gel column (4 cm*10 cm) using hexane/ethyl acetate (95/5) for elution. The fraction containing the desired product was stripped of all volatiles under vacuum to yield N-cyclopropylaniline (0.8 g). NMR (200 MHz, DMSO-d6): delta0.37 (m, 2H); 0.68 (m, 2H); 2.30 (m, 1H); 6.03 (br s, 1H); 6.56 (t, J=7.4 Hz, 1H); 6.70 (d, J=8.2 Hz, 2H); 7.09 (t, J=7.8 Hz, 2H) N-Cyclopropylaniline was then be coupled with 3-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)-benzyl)benzoyl chloride, deprotected and purified by the methods described in Example 10 to give 3-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-cyclopropyl-N-phenylbenzamide as a yellow powder. NMR (200 MHz, DMSO-d6): delta0.44 (m, 2H); 0.70 (m, 2H); 0.93 (d, J=6.1 Hz, 3H); 1.01 (d, J=5.7 Hz, 3H); 1.74 (dd, J1 =7.7 Hz, J2 =11.8 Hz, 1H); 2.05 (dd, J1 =6.8 Hz, J2 =11.1 Hz, 1H); 2.39 (br d, J=10.5 Hz, 1H); 2.41-2.54 (m, 2H); 2.69 (br d, J=11.8 Hz, 1H); 2.83 (dd, J1 =6.6 Hz, J2 =13.6 Hz, 1H); 3.05-3.36 (m, 2H); 4.83 (s, 1H); 5.10 (d, J=9.8 Hz, 1H); 5.17 (d, J=17.4 Hz, 1H); 5.70-5.86 (m, 1H); 6.57 (d, J=7.1 Hz, 1H); 6.63 (s, 1H); 6.65 (d, J=8.2 Hz, 1H); 7.03-7.38 (m, 10H); 9.34 (s, 1H). Mass spectrum (CI--CH4) m/e: 496 (M+1, 100%), 342 (45%), 153 (90%). [alpha]D20 =+7.1 (abs. ethanol, c=1.1).
Cyclopropylamine (1.0 g, 17.5 mmol.) was added to triphenylbismuth (9.25 g, 21.0 mmol.) and cupric acetate (1.6 g, 8.75 mmol) in dichloromethane (30 mL) at room temperature under nitrogen. The mixture was stirred for 18 hours, filtered over a short plug of celite to remove any insoluble material, and purified by chromatography on a silica gel column (4 cm*10 cm) using hexane/ethyl acetate (95/5) for elution. The fraction containing the desired product was stripped of all volatiles under vacuum to yield N-cyclopropylaniline (0.8 g). NMR (200 MHz, DMSO-d6): delta 0.37 (m, 2H); 0.68 (m, 2H); 2.30 (m, 1H); 6.03 (br s, 1H); 6.56 (t, J=7.4 Hz, 1H); 6.70 (d, J=8.2 Hz, 2H); 7.09 (t, J=7.8 Hz, 2H) N-Cyclopropylaniline was then be coupled with 3-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)-benzyl)benzoyl chloride, deprotected and purified by the methods described in Example 10 to give 3-((alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-cyclopropyl-N-phenylbenzamide as a yellow powder. NMR (200 MHz, DMSO-d6): delta 0.44 (m, 2H); 0.70 (m, 2H); 0.93 (d, J=6.1 Hz, 3H); 1.01 (d, J=5.7 Hz, 3H); 1.74 (dd, J1 =7.7 Hz, J2 =11.8 Hz, 1H); 2.05 (dd, J1 =6.8 Hz, J2 =11.1 Hz, 1H); 2.39 (br d, J=10.5 Hz, 1H); 2.41-2.54 (m, 2H); 2.69 (br d, J=11.8 Hz, 1H); 2.83 (dd, J1 =6.6 Hz, J2 =13.6 Hz, 1H); 3.05-3.36 (m, 2H); 4.83 (s, 1H); 5.10 (d, J=9.8 Hz, 1H); 5.17 (d, J=17.4 Hz, 1H); 5.70-5.86 (m, 1H); 6.57 (d, J=7.1 Hz, 1H); 6.63 (s, 1H); 6.65 (d, J=8.2 Hz, 1H); 7.03-7.38 (m, 10H); 9.34 (s, 1H). Mass spectrum (CI--CH4) m/e: 496 (M+1, 100%), 342 (45%), 153 (90%). [alpha]D20 =+7.1 (abs. ethanol, c=1.1).
  • 26
  • [ 121-44-8 ]
  • [ 598-21-0 ]
  • [ 34535-98-3 ]
  • [ 174180-98-4 ]
YieldReaction ConditionsOperation in experiment
In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; A. 2-Bromo-N-cyclopropyl-N-phenyl-acetamide To a stirred solution of 908 mg (6.83 mmol) <strong>[34535-98-3]Cyclopropyl-phenyl-amine</strong> (Kang, Sung, Kim, J. Chem. Soc., Chem. Commun., 1987, 897-898) and 690 mg (6.83 mmol, 1 equiv) Et3 N in 10 mL DCM is added 1.38 g (6.83 mmol, 1 equiv) Bromoacetyl bromide in 4 mL DCM dropwise over 15 minutes at 0 C. The reaction mixture is stirred 3 h at 0 C., diluted with 30 mL DCM, washed with 1N HCl (30 mL), dried (MgSO4), and concentrated in vacuo. The crude product is purified by flash chromatography on 30 g silica gel eluted successively with EtOAc/Hexanes (1:9, 100 mL), (3:17, 300 mL). Appropriate fractions were combined and concentrated in vacuo to give 948 mg (3.73 mmol) of 2-Bromo-N-cyclopropyl-N-phenyl-acetamide as an amber oil: 1 H NMR (CDCl3, 300 MHz) delta7.39 (m, 3H), 7.15 (m, 2H), 3.62 (s, br, 2H), 3.24 (m, 1H), 0.83 (m, 2H), 0.52 (m, 2H); TLC Rf =0.18 (EtOAc/Hexanes, 3:17).
  • 27
  • [ 34535-98-3 ]
  • [ 49617-83-6 ]
  • [ 950577-09-0 ]
YieldReaction ConditionsOperation in experiment
21% With potassium carbonate; In tetrahydrofuran; at 20℃; for 15h; N-cyclopropyl-N-(3-iodobenzyl)aniline N-cyclopropylaniline (type W, commercially available) (1.1 g) and 1-(bromomethyl)-3-iodobenzole (type X, commercially available) (2.5 g, 8.3 mmol) were dissolved in tetrahydrofuran (20 mL) and potassium carbonate (2.2 g, 16.6 mmol) added. The mixture was stirred approx. 15 h at RT and then placed on water (200 mL) and extracted with chloroform (100 mL). The organic phase was dried (MgSO4) and evaporated to low bulk. (Yield: 600 mg, 21%)
  • 28
  • [ 292638-84-7 ]
  • [ 34535-98-3 ]
  • N-(2-phenylcyclopentyl)aniline [ No CAS ]
  • N-(2-phenylcyclopentyl)aniline [ No CAS ]
  • 29
  • [ 1515-78-2 ]
  • [ 34535-98-3 ]
  • C19H21N [ No CAS ]
  • C19H21N [ No CAS ]
  • 30
  • [ 2039-88-5 ]
  • [ 34535-98-3 ]
  • N-(2-(2-bromophenyl)cyclopentyl)aniline [ No CAS ]
  • N-(2-(2-bromophenyl)cyclopentyl)aniline [ No CAS ]
  • 31
  • [ 75-36-5 ]
  • [ 34535-98-3 ]
  • 3-acetoxy-propionic acid anilide [ No CAS ]
  • 32
  • [ 107-13-1 ]
  • [ 34535-98-3 ]
  • C12H14N2 [ No CAS ]
  • C12H14N2 [ No CAS ]
  • 33
  • [ 34535-98-3 ]
  • (+/-)-cis-1,2,3,3a,4,8b-hexahydro-4-phenylcyclopent[b]indole [ No CAS ]
  • 34
  • [ 34535-98-3 ]
  • C22H25N [ No CAS ]
  • 35
  • [ 34535-98-3 ]
  • C14H17N [ No CAS ]
  • 36
  • [ 34535-98-3 ]
  • 1-phenyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[b]pyridine [ No CAS ]
  • 37
  • [ 34535-98-3 ]
  • C22H25N [ No CAS ]
  • 38
  • [ 34535-98-3 ]
  • (4aS,7aR)-1-Phenyl-octahydro-[1]pyrindine [ No CAS ]
  • 39
  • [ 62-53-3 ]
  • [ 34535-98-3 ]
  • 40
  • [ 34535-98-3 ]
  • [ 66223-76-5 ]
  • [ 103-84-4 ]
  • 41
  • [ 321532-64-3 ]
  • [ 34535-98-3 ]
  • 42
  • [ 536-74-3 ]
  • [ 34535-98-3 ]
  • N-(2-phenylcyclopent-2-en-1-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 43
  • [ 34535-98-3 ]
  • N-cyclopropyl-2-diazo-N-phenyl-2-(4-(trifluoromethyl)phenyl)acetamide [ No CAS ]
  • 44
  • [ 34535-98-3 ]
  • (S)-3-allyl-1-cyclopropyl-3-(4-(trifluoromethyl)phenyl)indolin-2-one [ No CAS ]
  • (R)-3-allyl-1-cyclopropyl-3-(4-(trifluoromethyl)phenyl)indolin-2-one [ No CAS ]
  • 45
  • [ 32857-62-8 ]
  • [ 34535-98-3 ]
  • N-cyclopropyl-N-phenyl-2-(4-(trifluoromethyl)phenyl)acetamide [ No CAS ]
  • 46
  • [ 292638-84-7 ]
  • [ 34535-98-3 ]
  • C17H19N [ No CAS ]
  • 47
  • [ 3814-93-5 ]
  • [ 34535-98-3 ]
  • C17H16(2)H3N [ No CAS ]
  • 48
  • [ 28920-43-6 ]
  • [ 34535-98-3 ]
  • (9H-fluoren-9-yl)methyl cyclopropyl(phenyl)carbamate [ No CAS ]
  • 49
  • [ 34535-98-3 ]
  • C17H15(2)H2NO2 [ No CAS ]
  • 50
  • [ 501-53-1 ]
  • [ 34535-98-3 ]
  • benzyl cyclopropyl(phenyl)carbamate [ No CAS ]
  • 51
  • [ 2680-03-7 ]
  • [ 34535-98-3 ]
  • N,N-dimethyl-2-(phenylamino)cyclopentanecarboxamide [ No CAS ]
  • N,N-dimethyl-2-(phenylamino)cyclopentanecarboxamide [ No CAS ]
  • 52
  • [ 624-48-6 ]
  • [ 34535-98-3 ]
  • dimethyl 3-(phenylamino)cyclopentane-1,2-dicarboxylate [ No CAS ]
  • 53
  • [ 34535-98-3 ]
  • [ 624-49-7 ]
  • dimethyl 3-(phenylamino)cyclopentane-1,2-dicarboxylate [ No CAS ]
  • 54
  • [ 405-99-2 ]
  • [ 34535-98-3 ]
  • N-(2-(4-fluorophenyl)cyclopentyl)aniline [ No CAS ]
  • N-(2-(4-fluorophenyl)cyclopentyl)aniline [ No CAS ]
  • 55
  • [ 1073-67-2 ]
  • [ 34535-98-3 ]
  • N-(2-(4-chlorophenyl)cyclopentyl)aniline [ No CAS ]
  • N-(2-(4-chlorophenyl)cyclopentyl)aniline [ No CAS ]
  • 56
  • [ 2039-82-9 ]
  • [ 34535-98-3 ]
  • N-(2-(4-bromophenyl)cyclopentyl)aniline [ No CAS ]
  • N-(2-(4-bromophenyl)cyclopentyl)aniline [ No CAS ]
  • 57
  • [ 622-97-9 ]
  • [ 34535-98-3 ]
  • N-(2-(p-tolyl)cyclopentyl)aniline [ No CAS ]
  • N-(2-(p-tolyl)cyclopentyl)aniline [ No CAS ]
  • 58
  • [ 1746-23-2 ]
  • [ 34535-98-3 ]
  • N-(2-(4-(tert-butyl)phenyl)cyclopentyl)aniline [ No CAS ]
  • N-(2-(4-(tert-butyl)phenyl)cyclopentyl)aniline [ No CAS ]
  • 59
  • [ 34535-98-3 ]
  • [ 98-83-9 ]
  • N-(2-methyl-2-phenylcyclopentyl)aniline [ No CAS ]
  • N-(2-methyl-2-phenylcyclopentyl)aniline [ No CAS ]
  • 60
  • [ 40307-11-7 ]
  • [ 34535-98-3 ]
  • N-(2-(4-ethyl phenyl)cyclopent-2-en-1-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 61
  • [ 34535-98-3 ]
  • [ 623-47-2 ]
  • ethyl 5-(phenylamino)cyclopent-1-enecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique;Catalytic behavior; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 62
  • [ 91-64-5 ]
  • [ 34535-98-3 ]
  • 1-(phenylamino)-1,3,3a,9b-tetrahydrocyclopenta[c]chromen-4(2H)-one [ No CAS ]
  • (1SR,4RS,7SR)-7-(2-hydroxyphenyl)-2-phenyl-2-azabicyclo[2.2.1]heptan-3-one [ No CAS ]
  • 63
  • [ 34535-98-3 ]
  • [ 140-88-5 ]
  • ethyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • ethyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 64
  • [ 292638-85-8 ]
  • [ 34535-98-3 ]
  • methyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • methyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 65
  • [ 141-32-2 ]
  • [ 34535-98-3 ]
  • butyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • butyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 66
  • [ 2499-95-8 ]
  • [ 34535-98-3 ]
  • hexyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • hexyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 67
  • [ 106-63-8 ]
  • [ 34535-98-3 ]
  • isobutyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • isobutyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 68
  • [ 1663-39-4 ]
  • [ 34535-98-3 ]
  • tert-butyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • tert-butyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 69
  • [ 103-11-7 ]
  • [ 34535-98-3 ]
  • 2-ethyl hexyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 2-ethyl hexyl 2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 70
  • [ 2455-24-5 ]
  • [ 34535-98-3 ]
  • (tetrahydrofuran-2-yl)methyl-1-methyl-2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • (tetrahydrofuran-2-yl)methyl-1-methyl-2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 71
  • [ 868-77-9 ]
  • [ 34535-98-3 ]
  • 2-hydroxyethyl 1-methyl-2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 2-hydroxyethyl 1-methyl-2-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 72
  • [ 623-43-8 ]
  • [ 34535-98-3 ]
  • methyl 2-methyl-5-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 73
  • [ 103-36-6 ]
  • [ 34535-98-3 ]
  • ethyl 2-phenyl-3-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • ethyl 2-phenyl-3-(phenylamino)cyclopentanecarboxylate [ No CAS ]
  • 74
  • [ 76782-82-6 ]
  • [ 34535-98-3 ]
  • N-(2-(((tert-butyldimethylsilyl)oxy)methyl)cyclopent-2-en-1-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 75
  • [ 34535-98-3 ]
  • [ 768-60-5 ]
  • N-(2-(4-methoxyphenyl)cyclopent-2-en-1-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 76
  • [ 766-98-3 ]
  • [ 34535-98-3 ]
  • N-(2-(4-fluorophenyl)cyclopent-2-en-1-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 77
  • [ 2809-69-0 ]
  • [ 34535-98-3 ]
  • N-(3-methyl-2-(prop-1-yn-1-yl)cyclopent-2-en-1-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 78
  • [ 13633-26-6 ]
  • [ 34535-98-3 ]
  • C19H19N [ No CAS ]
  • C19H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
13%; 28% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 79
  • [ 5622-76-4 ]
  • [ 34535-98-3 ]
  • C19H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With C60H96N4O12Rh2; In 1,2-dichloro-ethane; at 20℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube equipped with a stirring bar was charged with Rh2(5S,R-MenPY)4 (0.1 mol %), alkyne (5.0 mmol), and dry DCE (5 mL). The tube was degassed through three freeze-pump-thaw cycles. After evacuating and backfilling the tube with argon three times, cyclopropylamine (1 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours. After the reaction was complete, the mixture was concentrated and the residue was purified by flash chromatography to obtain the desired allylic amine.
  • 80
  • [ 98-95-3 ]
  • [ 411235-57-9 ]
  • [ 34535-98-3 ]
YieldReaction ConditionsOperation in experiment
55% With triethylphosphine; In m-xylene; at 120℃; for 9h;Inert atmosphere; Schlenk technique; Sealed tube; General procedure: A glass culture tube containing a magnetic stir bar was charged with a nitroarene substrate and boronic acid, then fitted with a PTFE-lined silicone septum within a phenolic screw-thread open-top cap after wrapping the reaction tube thread once with Teflon tape. The vessel was evacuated and backfilled with nitrogen on a Schlenk line. Dry m-xylene (2 mL, 0.5 M) was added via syringe, followed by triethylphosphine (0.44 mL, 3 equivalents) and the reaction mixturewas heated 120 C with stirring. Upon completion, the reaction mixture was cooled to ambient temperature then diluted with 10 mL of distilled water. With the aid of ethyl acetate (ca. 3 x 10 mL), the reaction mixture was transferred to a separatory funnel. After mixing and separating the phases, the organic layer was washed with 10 mL of a 1M NaOH aqueous solution, and 10 mL of brine. Each aqueous phase was back-extracted with one 10 mL portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The crude residues were purified via column chromatography to yield pure coupling products. Columns were primarily slurry packed with hexanes and mobile phase polarity was increased gradually to the mixture indicated. Note: hexanes = Hex, dichloromethane = DCM, ethyl acetate = EA.
  • 81
  • (2R,3R)-3-bromo-1,2-epoxy-hexane [ No CAS ]
  • [ 34535-98-3 ]
  • N-cyclopropyl-N-(((2R,3S)-3-propyloxirane-2-yl)methyl)aniline [ No CAS ]
  • 82
  • [ 7677-24-9 ]
  • [ 34535-98-3 ]
  • C10H11IN2 [ No CAS ]
  • 83
  • [ 1551163-94-0 ]
  • [ 34535-98-3 ]
  • C20H17N3 [ No CAS ]
  • C20H17N3 [ No CAS ]
  • 84
  • [ 1275621-08-3 ]
  • [ 34535-98-3 ]
  • C19H19F2N [ No CAS ]
  • C19H19F2N [ No CAS ]
  • 85
  • C15H18O2 [ No CAS ]
  • [ 34535-98-3 ]
  • C24H29NO2 [ No CAS ]
  • 86
  • [ 34535-98-3 ]
  • C21H19NO3 [ No CAS ]
  • 87
  • dimethyl 2-(4-tert-butylphenyl)cycloprop-2-ene-1,1-dicarboxylate [ No CAS ]
  • [ 34535-98-3 ]
  • C26H31NO4 [ No CAS ]
  • C26H31NO4 [ No CAS ]
  • 88
  • C13H11FO4 [ No CAS ]
  • [ 34535-98-3 ]
  • C22H22FNO4 [ No CAS ]
  • C22H22FNO4 [ No CAS ]
  • 89
  • C9H5BrF2 [ No CAS ]
  • [ 34535-98-3 ]
  • C18H16BrF2N [ No CAS ]
  • C18H16BrF2N [ No CAS ]
  • 90
  • 1-(3,3-difluorocycloprop-1-en-1-yl)-4-methoxybenzene [ No CAS ]
  • [ 34535-98-3 ]
  • C19H19F2NO [ No CAS ]
  • C19H19F2NO [ No CAS ]
  • 91
  • C9H5ClF2 [ No CAS ]
  • [ 34535-98-3 ]
  • C18H16ClF2N [ No CAS ]
  • C18H16ClF2N [ No CAS ]
  • 92
  • [ 34535-98-3 ]
  • [ 570431-68-4 ]
  • C19H27NO4Si [ No CAS ]
  • C19H27NO4Si [ No CAS ]
  • 93
  • [ 102127-47-9 ]
  • [ 34535-98-3 ]
  • C16H19NO4 [ No CAS ]
  • 94
  • [ 34535-98-3 ]
  • [ 170751-24-3 ]
  • C22H23NO4 [ No CAS ]
  • C22H23NO4 [ No CAS ]
  • 95
  • [ 1083094-27-2 ]
  • [ 34535-98-3 ]
  • C34H31NO4 [ No CAS ]
  • C34H31NO4 [ No CAS ]
  • 96
  • C15H10F6O4 [ No CAS ]
  • [ 34535-98-3 ]
  • C24H21F6NO4 [ No CAS ]
  • C24H21F6NO4 [ No CAS ]
  • 97
  • [ 1493-27-2 ]
  • [ 34535-98-3 ]
  • C15H14N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; sodium hydride; at 17℃; for 30h; The temperature is 17 C at room temperature,Humidity is 52%, magnetically stirred. In a 500 ml two-necked round bottom flask, compound 1-b (13.0 g, 97.6 mmol, 1 eq) and o-fluoronitrobenzene (48.2 g, 341.6 mmol, 3.5 eq) were sequentially added, and 250 ml of pyridine was used as a solvent , Stirred at room temperature, and finally added sodium hydride (23.6 g, 590 mmol, 6.0 eq) in portions. After 30 h, TLC monitored that the raw materials were basically complete. In an ice-ethanol bath, slowly add water to quench NaH. After quenching is complete, EA (ethyl acetate) is extracted once. The aqueous phase is filtered through diatomaceous earth to remove suspended matter, and then extracted again with EA. The organic phase After the combination, it was washed with dilute HCl until the aqueous phase became weakly acidic, dried over anhydrous magnesium sulfate, filtered with suction, concentrated, packed with 200 g * 2 silica gel, and wet-loaded to obtain 48 g of colorless oily product (Compound 1-c) , With a purity of 50%
  • 98
  • [ 98720-98-0 ]
  • [ 62-53-3 ]
  • [ 34535-98-3 ]
YieldReaction ConditionsOperation in experiment
With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol; at 60℃; for 7.5h; The temperature was 20 C at room temperature and 60% air humidity. Under magnetic stirring, compound 1-a (15g, 161.1mmol, 1eq) was added to a 500ml three-neck round bottom flask, and 120ml (MeOH: THF = 1: 1) was used as a solvent. Then add glacial acetic acid (12.6g, 209.8mmol, 1.5eq) and 1-ethoxy-1-trimethylsilylcyclopropane (28g, 161.6mmol, 1eq), and finally slowly add sodium cyanoborohydride (20.2g, 321.4 mmol, 2 eq), exothermic during the addition, the reaction solution was colorless and transparent, and the reaction was maintained at a temperature of 60 C. After 7.5 h, the basic reaction of the raw materials was monitored by TLC.After the temperature was lowered to room temperature, 200 ml of n-hexane was added to the reaction, and the solid was removed by suction filtration. After the filtrate was concentrated, 200 g of silica gel was packed in a column and wet-loaded to obtain 13.0 g of a pale yellow oil, namely compound 1-b. Yield: 60.7%, purity: 60%
  • 99
  • [ 34535-98-3 ]
  • C15H16N2 [ No CAS ]
  • 100
  • [ 34535-98-3 ]
  • [ 1024010-56-7 ]
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