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Name 17-Iodoandrosta-5,16-dien-3beta-ol
EINECS1592732-453-0
CAS No. 32138-69-5
Density1.459 g/cm³
PSA20.23000
LogP5.23890
SolubilityN/A
Melting Point175-176 °C
FormulaC₁₉H₂₇IO
Boiling Point447.471 °C at 760 mmHg
Molecular Weight398.327
Flash Point224.423 °C
Transport InformationN/A
AppearanceN/A
Safety
Risk CodesN/A
Molecular Structure
Hazard SymbolsN/A
SynonymsN/A
Article Data27

17-Iodoandrosta-5,16-dien-3beta-ol Synthetic route

: 17-iodoandrosta-5,16-dien-3β-ol 3-acetate

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; methanol at 30℃; for 1h; Inert atmosphere;	99%

: 63015-10-1
dehydroepiandrosterone-17-hydrazone

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
With iodine; guanidine nitrate In tetrahydrofuran 1) 15 min, room temp., 2) 5 hrs, 80 deg C without solvent;	95%
With iodine; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; diethyl ether at 0℃; for 2h;	92.4%
With iodine; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; diethyl ether at 0℃; for 2h;	92.4%

: 63015-10-1, 77059-27-9
androstenone hydrazone

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine 1.) THF, 15 min, 2.) 80 deg C, 5 h;	95%

: 1232-19-5, 13996-45-7, 2830-48-0
17-hydroxyiminoandrost-5-en-3β-ol

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
With iodine; triethylamine In tetrahydrofuran for 3h; Cooling with ice;	91.08%

: 53-43-0
dehydroepiandrosterone

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
Stage #1: dehydroepiandrosterone With hydrazine hydrate; hydrazinium sulfate In ethanol; water at 20℃; for 96h; Stage #2: With iodine; triethylamine In 1,4-dioxane for 1.5h;	62%
Multi-step reaction with 2 steps 1: hydrazine hydrate; aq. hydrazine sulfate / ethanol / 12 h / 20 °C 2: 92.4 percent / iodine; 1,1,3,3-tetramethylguanidine / tetrahydrofuran; diethyl ether / 2 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: hydrazine hydrate, triethylamine / ethanol 2: 95 percent / I2, BTMG / 1.) THF, 15 min, 2.) 80 deg C, 5 h View Scheme

: (3S,8R,9S,10R,13S,14S)-17-Hydrazino-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
With iodine; triethylamine

: 63015-10-1, 77059-27-9
androstenone hydrazone

A: 32138-69-5
17-iodo-5,16-androstadien-3-ol

B: 86770-60-7
17,17-diiodo-3β-hydroxy-5-androstene

Conditions

Conditions	Yield
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; iodine In tetrahydrofuran Yield given. Yields of byproduct given;
With iodine In tetrahydrofuran Product distribution; effect of base (TMG, BTMG);

: 53-43-0
dehydroepiandrosterone

3α-hydroxy-androsten-(5)-one-(17): 3α-hydroxy-androsten-(5)-one-(17)

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / NH2NH2H2O, aq, NH2NH2H2SO4 / ethanol / 120 h / Ambient temperature 2: 83 percent / I2, 1,1,3,3-tetramethylguanidine / tetrahydrofuran; diethyl ether / 1 h View Scheme

: 853-23-6
prasterone acetate

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. N2H4, Et3N / ethanol / Heating 2: I2, Et3N / tetrahydrofuran; ethanol View Scheme
Multi-step reaction with 3 steps 1: hydrazine hydrate; hydrazinium sulfate / ethanol; water / 12 h / 20 °C / Inert atmosphere 2: iodine; N,N,N',N'-tetramethylguanidine / tetrahydrofuran; diethyl ether / 2 h / 0 °C 3: potassium hydroxide / tetrahydrofuran; methanol / 1 h / 30 °C / Inert atmosphere View Scheme

: 122914-94-7
3β-acetoxyandrost-5-en-17-hydrazone

: 32138-69-5
17-iodo-5,16-androstadien-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: iodine; N,N,N',N'-tetramethylguanidine / tetrahydrofuran; diethyl ether / 2 h / 0 °C 2: potassium hydroxide / tetrahydrofuran; methanol / 1 h / 30 °C / Inert atmosphere View Scheme

17-Iodoandrosta-5,16-dien-3beta-ol Specification

The 17-Iodoandrosta-5,16-dien-3beta-ol, with the CAS registry number 32138-69-5, is also known as 3β-Hydroxy-17-iodo-androsta-5,16-diene. This chemical's molecular formula is C₁₉H₂₇IO and molecular weight is 398.32. What's more, its systematic name is (3S,10R,13S)-17-iodo-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol.

Physical properties of 17-Iodoandrosta-5,16-dien-3beta-ol are: (1)ACD/LogP: 5.215; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.22; (4)ACD/LogD (pH 7.4): 5.22; (5)ACD/BCF (pH 5.5): 5408.74; (6)ACD/BCF (pH 7.4): 5408.74; (7)ACD/KOC (pH 5.5): 16358.45; (8)ACD/KOC (pH 7.4): 16358.45; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 20.23 Å²; (13)Index of Refraction: 1.618; (14)Molar Refractivity: 95.608 cm³; (15)Molar Volume: 273.058 cm³; (16)Polarizability: 37.902×10^-24cm³; (17)Surface Tension: 47.827 dyne/cm; (18)Density: 1.459 g/cm³; (19)Flash Point: 224.423 °C; (20)Enthalpy of Vaporization: 81.443 kJ/mol; (21)Boiling Point: 447.471 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: C[C@]12CC[C@@H](CC1=CCC3C2CC[C@]4(C3CC=C4I)C)O
(2)Std. InChI: InChI=1S/C19H27IO/c1-18-9-7-13(21)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,6,13-16,21H,4-5,7-11H2,1-2H3/t13-,14?,15?,16?,18-,19-/m0/s1
(3)Std. InChIKey: DHZJEYGWSNDRGN-INNQQZFDSA-N

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Product Name

17-Iodoandrosta-5,16-dien-3beta-ol

17-Iodoandrosta-5,16-dien-3beta-ol Synthetic route

17-Iodoandrosta-5,16-dien-3beta-ol Specification

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