7-Ethylcamptothecin supplier | CasNO.78287-27-1

Name
7-Ethylcamptothecin
EINECS
CAS No. 78287-27-1
Article Data12
CAS DataBase
Density 1.436 g/cm³
Solubility
Melting Point 236-241oC
Formula C₂₂H₂₀N₂O₄
Boiling Point 752.867 °C at 760 mmHg
Molecular Weight 376.412
Flash Point 409.119 °C
Transport Information
Appearance light pink solid
Safety 3/14-6-36/37/39
Risk Codes 23/34/35
Molecular Structure
Hazard Symbols
Synonyms 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4,11-diethyl-4-hydroxy-, (S)-;7-Ethyl-20(S)-camptothecin;SN 22;
PSA 81.42000
LogP 2.64200

Synthetic route

: 123-38-6
propionaldehyde

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; acetic acid at -5 - 5℃; for 0.166667h; Temperature;	95.4%
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water for 3h; Ambient temperature;	77%
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate for 3h; Ambient temperature;	77%

: 3425-61-4
tert-amyl hydroperoxide

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; iron(II) sulfate; acetic acid In water at 0℃; for 0.5h;	83.3%

: 148550-34-9
Acetic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A: 78287-27-1
7-ethylcamptothecin

B: 152266-85-8
(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 2.5h; Heating;	A 74% B 11%

: 4433-63-0
Ethyl boronic acid

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; 1-acetoxy-1,2-benziodoxol-3-one at 30℃; for 48h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation;	60%

: 71-23-8
propan-1-ol

: 7689-03-4
camptothecin

A: 78287-27-1
7-ethylcamptothecin

B: 139080-89-0
7(3-Hydroxy-1-propyl)camptothecin

C: 96962-27-5
7-(1-Hydroxy-2-propyl)camptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water for 3h; Ambient temperature;	A 40% B 12% C 22%

...Expand

: 7689-03-4
camptothecin

: 96-22-0
pentan-3-one

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water; acetic acid for 48h; Ambient temperature;	22%

: 802294-64-0
propionic acid

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water for 48h; Ambient temperature;	13%

: 148550-35-0
Isobutyric acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A: 78287-27-1
7-ethylcamptothecin

B: 152266-85-8
(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 2.5h; Heating;	A 10 % Chromat. B 16 % Chromat.

: 120730-50-9
Benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A: 78287-27-1
7-ethylcamptothecin

B: 152266-85-8
(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 2.5h; Heating;	A 38 % Chromat. B 36 % Chromat.

: 120730-51-0
4-Methoxy-benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A: 78287-27-1
7-ethylcamptothecin

B: 152266-85-8
(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 2.5h; Heating;	A 20 % Chromat. B 46 % Chromat.

: 4-Cyano-benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A: 78287-27-1
7-ethylcamptothecin

B: 152266-85-8
(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions

Conditions	Yield
With hydrazine hydrate In methanol for 2.5h; Heating;	A 42 % Chromat. B 46 % Chromat.

: ferrous(II) sulfate heptahydrate

: 123-38-6
propionaldehyde

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; acetic acid In water

...Expand

: ferrous(II) sulfate heptahydrate

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; propionic acid In water

: 71-23-8
propan-1-ol

: ferrous(II) sulfate heptahydrate

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide In water

...Expand

: ferrous(II) sulfate heptahydrate

: 7689-03-4
camptothecin

: 96-22-0
pentan-3-one

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; acetic acid In water

...Expand

: 955939-02-3
7-ethyl-18,19-dehydrocamptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In 1,4-dioxane; ethanol at 20℃; for 1 - 7h;

: 75-07-0
acetaldehyde

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With ferrous(II) sulfate heptahydrate; sulfuric acid; dihydrogen peroxide In water at 0℃; for 8h;

: 78287-27-1
7-ethylcamptothecin

: 797762-11-9
7-ethyl-1,2,6,7-tetrahydro-20-(S)-camptothecin

Conditions

Conditions	Yield
With hydrogen; N113 In acetic acid at 110℃; under 15001.5 Torr; for 6h; Autoclave;	96%
With hydrogen; dimethyl sulfoxide; platinum on carbon In acetic acid at 25 - 65℃; under 3750.38 Torr; for 43.5h;

: 13734-41-3
t-Boc-L-valine

: 78287-27-1
7-ethylcamptothecin

: C32H37N3O7

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 20h;	92%

: 78287-27-1
7-ethylcamptothecin

: 56059-30-4
5-fluorouracil-1-acetic acid

: C28H23FN4O7

Conditions

Conditions	Yield
Stage #1: 5-fluorouracil-1-acetic acid With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃; Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;	88%

: 4113-97-7
uracilacetic acid

: 78287-27-1
7-ethylcamptothecin

: C28H24N4O7

Conditions

Conditions	Yield
Stage #1: uracilacetic acid With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃; Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;	86.6%

: 78287-27-1
7-ethylcamptothecin

: 57846-83-0
2-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid

: C28H23IN4O7

Conditions

Conditions	Yield
Stage #1: 2-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃; Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;	86.6%

: 78287-27-1
7-ethylcamptothecin

: 75-31-0
isopropylamine

: (S)-2-(12-Ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-N-isopropyl-butyramide

Conditions

Conditions	Yield
for 1.5h; Heating;	86%

: 95209-81-7
1-carboxymethyl-5-chlorouracil

: 78287-27-1
7-ethylcamptothecin

: C28H23ClN4O7

Conditions

Conditions	Yield
Stage #1: 1-carboxymethyl-5-chlorouracil With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃; Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;	84%

: 402-54-0
p-nitrobenzotrifluoride

: 78287-27-1
7-ethylcamptothecin

: 7-ethylcamptothecin-20(S)-O-p-triflouoromethylbenzoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 2 - 20℃; for 2.25h;	82%

: 78287-27-1
7-ethylcamptothecin

: 86639-52-3, 110714-48-2, 130144-34-2
7-ethyl-10-hydroxycamptothecin

Conditions

Conditions	Yield
With dihydrogen peroxide; acetic anhydride; acetic acid at 50℃;	80.3%
Multi-step reaction with 2 steps 1: 77.7 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C 2: 49.1 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation View Scheme
Multi-step reaction with 2 steps 1: 78 percent / 30percent H2O2 / acetic acid / 3.5 h / 70 - 80 °C 2: 49 percent / 1 N H2SO4 / dioxane / 0.5 h / Irradiation View Scheme
Stage #1: 7-ethylcamptothecin With hydrogen; acetic acid; platinum(IV) oxide In dimethyl sulfoxide at 50 - 60℃; under 3102.97 Torr; for 10h; Stage #2: With [bis(acetoxy)iodo]benzene In water at 20℃; for 3h;
Multi-step reaction with 2 steps 1: acetic acid; dihydrogen peroxide / 8 h / 80 °C 2: sulfuric acid; water / 1,4-dioxane; acetonitrile / Inert atmosphere; Irradiation View Scheme

: 31385-63-4
(5-bromouracil)acetic acid

: 78287-27-1
7-ethylcamptothecin

: C28H23BrN4O7

Conditions

Conditions	Yield
Stage #1: (5-bromouracil)acetic acid With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃; Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;	80%

: 78287-27-1
7-ethylcamptothecin

: 86639-51-2
7-Ethylcamptothecin 1-Oxide

Conditions

Conditions	Yield
With dihydrogen peroxide In acetic acid at 70 - 80℃; for 3.5h;	78%
With dihydrogen peroxide; acetic acid at 70 - 80℃; for 3.5h;	77.7%
With dihydrogen peroxide; acetic acid at 80℃; for 8h;	72%

: 78287-27-1
7-ethylcamptothecin

: 121-92-6
3-nitrobenzoic acid

: 7-ethylcamptothecin-20(S)-O-m-nitrobenzoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 2 - 20℃; for 2.25h;	77.1%

: 78287-27-1
7-ethylcamptothecin

: 108-00-9
N,N-dimethylethylenediamine

: 120730-44-1
(S)-N-(2-Dimethylamino-ethyl)-2-(12-ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-butyramide

Conditions

Conditions	Yield
at 50℃; for 1.5h;	71%

: 78287-27-1
7-ethylcamptothecin

: 106-96-7
propargyl bromide

: 2-propyn-1-yl-7-ethylcamptothecin

Conditions

Conditions	Yield
Stage #1: 7-ethylcamptothecin With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide Inert atmosphere; Reflux;	70%

: 78287-27-1
7-ethylcamptothecin

: 2-Amino-4,11-diethyl-2H,12H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions

Conditions	Yield
With hydrazine hydrate for 2h; Heating;	64%

: 78287-27-1
7-ethylcamptothecin

: 1258494-58-4
7-ethyl-14-nitro-camptothecin

Conditions

Conditions	Yield
With nitric acid; acetic anhydride at 0℃; for 1h;	63.4%

: 78287-27-1
7-ethylcamptothecin

: 58-85-5
biotin

: biotin-(20s)-7-ethylcamptothecin

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	57%

: 78287-27-1
7-ethylcamptothecin

: 72040-64-3
N-(+)-biotinyl-6-aminocaproic acid

: 6-biotinylaminocaproic acid-(20s)-7-ethylcamptothecin

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	56%

: C17H20N2O4S2

: C28H29ClNO2(1+)*I(1-)

: 78287-27-1
7-ethylcamptothecin

: C69H65ClN5O13S2(1+)*I(1-)

Conditions

Conditions	Yield
Stage #1: C17H20N2O4S2 With pyridine In tetrahydrofuran for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With trichloromethyl chloroformate In tetrahydrofuran for 1h; Stage #3: C28H29ClNO2(1+)*I(1-); 7-ethylcamptothecin With dmap; triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Cooling with ice;	31%

...Expand

: 78287-27-1
7-ethylcamptothecin

: 152266-83-6
12-Ethyl-8-methyl-7-propionyl-11H-indolizino[1,2-b]quinolin-9-one

Conditions

Conditions	Yield
With sodium azide; 18-crown-6 ether In N,N-dimethyl-formamide at 120℃; for 4h;	20%

: 78287-27-1
7-ethylcamptothecin

: 1026285-00-6
(S)-2-(12-Ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-butyric acid hydrazide

Conditions

Conditions	Yield
With hydrazine hydrate for 0.5h; Ambient temperature;

7-Ethylcamptothecin Specification

The IUPAC name of this chemical is 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4-hydroxy-, (S)-. With the CAS registry number 78287-27-1, it is also named as 7-Ethylcamptothecin. In addition, the molecular formula is C₂₂H₂₀N₂O₄ and the molecular weight is 376.41. It belongs to the classes of Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. What's more, it is a kind of light pink solid.

Physical properties about this chemical are: (1)ACD/LogP: 1.98; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.699; (4)ACD/LogD (pH 7.4): 1.973; (5)ACD/BCF (pH 5.5): 9.864; (6)ACD/BCF (pH 7.4): 18.55; (7)ACD/KOC (pH 5.5): 149.206; (8)ACD/KOC (pH 7.4): 280.597; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 79.73 Å²; (13)Index of Refraction: 1.713; (14)Molar Refractivity: 102.699 cm³; (15)Molar Volume: 262.079 cm³; (16)Polarizability: 40.713 ×10^-24cm³; (17)Surface Tension: 73.455 dyne/cm; (18)Density: 1.436 g/cm³; (19)Flash Point: 409.119 °C; (20)Enthalpy of Vaporization: 115.124 kJ/mol; (21)Boiling Point: 752.867 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation of 7-Ethylcamptothecin: it can be prepared by propionaldehyde and (S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione. This reaction will need reagents conc.H₂SO₄, 30percent H₂O₂ and FeSO₄*7H₂O and solvent H₂O. The reaction time is 3 hours at ambient temperature. The yield is about 77%.

7-Ethylcamptothecin can be prepared by propionaldehyde and (S)-4-ethyl-4-hydroxy-1,12-dihydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione

Uses of 7-Ethylcamptothecin: it can be used to get 2-amino-4,11-diethyl-2H,12H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione. This reaction will need reagent NH₂NH₂*H₂O. The reaction time is 2 hours by heating. The yield is about 64%.

7-Ethylcamptothecin can be used to get 2-amino-4,11-diethyl-2H,12H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione.

You can still convert the following datas into molecular structure:
(1)SMILES: CCc1c2ccccc2nc-3c1Cn4c3cc5c(c4=O)COC(=O)[C@]5(CC)O
(2)InChI: InChI=1/C22H20N2O4/c1-3-12-13-7-5-6-8-17(13)23-19-14(12)10-24-18(19)9-16-15(20(24)25)11-28-21(26)22(16,27)4-2/h5-9,27H,3-4,10-11H2,1-2H3/t22-/m1/s1
(3)InChIKey: MYQKIWCVEPUPIL-JOCHJYFZBZ

Product Name

7-Ethylcamptothecin

Synthetic route

7-Ethylcamptothecin Specification

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