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9-Methoxycamptothecin
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Name

9-Methoxycamptothecin

 EINECS N/A
CAS No. 39026-92-1 Density 1.5 g/cm3
PSA 90.65000 LogP 2.08820
Solubility N/A Melting Point 223-225℃
Formula C21H18N2O5 Boiling Point 773.1 °C at 760 mmHg
Molecular Weight 378.384 Flash Point 421.4 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 39026-92-1 ((4S)-4-Ethyl-4-hydroxy-10-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione) Hazard Symbols N/A
Synonyms

{1H-Pyrano[3,} {4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione-,} 4-ethyl-4-hydroxy-10-methoxy-, (S)-;Camptothecin, 9-methoxy-;9-Methoxycamptothecine;CAMPTOTHECIN,9-METHOXY;4-Ethyl-4-hydroxy-10-methoxy-1H-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;1H-Pyrano(3,4:6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione-, 4-ethyl-4-hydroxy-10-methoxy-, (S)-;1H-Pyrano[3, 4:6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione-, 4-ethyl-4-hydroxy-10-methoxy-, (S)-;

Article Data 4

9-Methoxycamptothecin Synthetic route

186581-53-3, 908094-01-9

diazomethane

67656-30-8

10-hydroxycamptothecin

39026-92-1

9-methoxycamptothecin

Conditions
ConditionsYield
In 1,4-dioxane; methanol; diethyl ether for 1h; Ambient temperature;95.5%
94%
91421-43-1

9-amino-20(S)-camptothecin

39026-92-1

9-methoxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 36 percent / aq. NaNO2; H2SO4 / Heating
View Scheme
Multi-step reaction with 2 steps
1: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h
2: 95.5 percent / methanol; dioxane; diethyl ether / 1 h / Ambient temperature
View Scheme
91421-42-0

rubitecan

39026-92-1

9-methoxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / SnCl2; Sn; aq. HCl
2: 36 percent / aq. NaNO2; H2SO4 / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr
2: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h
3: 95.5 percent / methanol; dioxane; diethyl ether / 1 h / Ambient temperature
View Scheme
7689-03-4

camptothecin

39026-92-1

9-methoxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 24 percent / aq. HNO3; H2SO4
2: 81 percent / SnCl2; Sn; aq. HCl
3: 36 percent / aq. NaNO2; H2SO4 / Heating
View Scheme
20-O-acetyl-10-methoxycamptothecin

20-O-acetyl-10-methoxycamptothecin

86639-48-7

Camptothecin 1-oxide

7688-64-4

(20S)-20-O-Acetylcamptothecin

57-15-8

1,1,1-trichloro-2-methyl-2-propanol

39026-92-1

9-methoxycamptothecin

Conditions
ConditionsYield
With pyridine; sulfuric acid; acetic anhydride In 1,4-dioxane; methanol
39026-92-1

9-methoxycamptothecin

142727-51-3

7-ethyl-10-hydroxy-mappicine ketone

Conditions
ConditionsYield
for 0.116667h; Irradiation;94%
In various solvent(s) at 200℃; for 9.5h;79%
for 0.116667h; Irradiation;
108-24-7

acetic anhydride

39026-92-1

9-methoxycamptothecin

39026-93-2

9-methoxycamptothecin acetate

Conditions
ConditionsYield
With lithium bromide at 20℃; for 24h;62%
39026-92-1

9-methoxycamptothecin

142727-79-5

9-methoxymappicine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.12 h / Irradiation
2: 91 percent / NaBH4 / methanol
View Scheme
Multi-step reaction with 2 steps
1: 94 percent / 0.12 h / Irradiation
2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature
View Scheme
39026-92-1

9-methoxycamptothecin

(R)-9-methoxymappicine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 0.12 h / Irradiation
2.1: NaBH4 / methanol
2.2: Candida cylindracea lipase; vinyl acetate / CHCl3 / 168 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 94 percent / 0.12 h / Irradiation
2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature
3: 82 percent / pyridine / Ambient temperature
4: 45 percent / lipase Amano PS (Pseudomonas cepacia), phosphate buffer / tetrahydrofuran / 72 h
View Scheme
Multi-step reaction with 5 steps
1: 94 percent / 0.12 h / Irradiation
2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature
3: 82 percent / pyridine / Ambient temperature
4: 47 percent / Baker's yeast (Saccharomyces cerevisiae), sucrose / H2O / 192 h / Ambient temperature
5: 98 percent / 10 percent aq. K2CO3 / methanol / 2 h / Heating
View Scheme
39026-92-1

9-methoxycamptothecin

243846-86-8

(S)-9-methoxymappicine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 0.12 h / Irradiation
2: 91 percent / NaBH4 / methanol
3: Candida cylindracea lioase / CHCl3 / 168 h / 20 °C
4: 10 percent aq. K2CO3 / methanol / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: 0.12 h / Irradiation
2.1: NaBH4 / methanol
2.2: Candida cylindracea lipase; vinyl acetate / CHCl3 / 168 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 94 percent / 0.12 h / Irradiation
2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature
3: 82 percent / pyridine / Ambient temperature
4: 45 percent / lipase Amano PS (Pseudomonas cepacia), phosphate buffer / tetrahydrofuran / 72 h
5: 96 percent / 10 percent aq.K2CO3 / methanol / 2 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 94 percent / 0.12 h / Irradiation
2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature
3: 82 percent / pyridine / Ambient temperature
4: 47 percent / Baker's yeast (Saccharomyces cerevisiae), sucrose / H2O / 192 h / Ambient temperature
View Scheme

9-Methoxycamptothecin Specification

The 9-Methoxycamptothecin is an organic compound with the formula C21H18N2O5. The systematic name of this chemical is (4S)-4-ethyl-4-hydroxy-10-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione. With the CAS registry number 39026-92-1, it is also named as 1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-10-methoxy-, (4S)-.

Physical properties about 9-Methoxycamptothecin are: (1)ACD/LogP: 2.00; (2)ACD/LogD (pH 5.5): 1.95; (3)ACD/LogD (pH 7.4): 2; (4)ACD/BCF (pH 5.5): 17.47; (5)ACD/BCF (pH 7.4): 19.34; (6)ACD/KOC (pH 5.5): 261.86; (7)ACD/KOC (pH 7.4): 289.95; (8)#H bond acceptors: 7; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 77.96 Å2; (12)Index of Refraction: 1.722; (13)Molar Refractivity: 99.81 cm3; (14)Molar Volume: 251.9 cm3; (15)Polarizability: 39.56×10-24cm3; (16)Surface Tension: 77.4 dyne/cm; (17)Density: 1.5 g/cm3; (18)Flash Point: 421.4 °C; (19)Enthalpy of Vaporization: 118.05 kJ/mol; (20)Boiling Point: 773.1 °C at 760 mmHg; (21)Vapour Pressure: 3.78E-25 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C\1N4\C(=C/C2=C/1COC(=O)[C@]2(O)CC)c3nc5c(cc3C4)c(OC)ccc5
(2)InChI: InChI=1/C21H18N2O5/c1-3-21(26)14-8-16-18-11(7-12-15(22-18)5-4-6-17(12)27-2)9-23(16)19(24)13(14)10-28-20(21)25/h4-8,26H,3,9-10H2,1-2H3/t21-/m0/s1
(3)InChIKey: XVMZDZFTCKLZTF-NRFANRHFBW
(4)Std. InChI: InChI=1S/C21H18N2O5/c1-3-21(26)14-8-16-18-11(7-12-15(22-18)5-4-6-17(12)27-2)9-23(16)19(24)13(14)10-28-20(21)25/h4-8,26H,3,9-10H2,1-2H3/t21-/m0/s1
(5)Std. InChIKey: XVMZDZFTCKLZTF-NRFANRHFSA-N

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