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7-Ethylcamptothecin
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  • Name 7-Ethylcamptothecin
  • EINECSN/A
  • CAS No. 78287-27-1
  • Density1.436 g/cm3
  • PSA81.42000
  • LogP2.64200
  • SolubilityN/A
  • Melting Point236-241oC
  • FormulaC22H20N2O4
  • Boiling Point752.867 °C at 760 mmHg
  • Molecular Weight376.412
  • Flash Point409.119 °C
  • Transport InformationN/A
  • Appearancelight pink solid
  • Safety3/14-6-36/37/39
  • Risk Codes23/34/35
  • Molecular Structure
    Molecular Structure of 78287-27-1 (7-Ethylcamptothecin)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data12

7-Ethylcamptothecin Synthetic route

123-38-6

propionaldehyde

7689-03-4

camptothecin

78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water for 3h; Ambient temperature;A 40%
B 12%
C 22%
7689-03-4

camptothecin

96-22-0

pentan-3-one

78287-27-1

7-ethylcamptothecin

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

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

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