Product Name

  • Name

    Lasofoxifene

  • EINECS
  • CAS No. 180916-16-9
  • Article Data7
  • CAS DataBase
  • Density 1.15 g/cm3
  • Solubility
  • Melting Point 110-113°C
  • Formula C28H31NO2
  • Boiling Point 572.4 °C at 760 mmHg
  • Molecular Weight 413.56
  • Flash Point 300 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 180916-16-9 (Lasofoxifene)
  • Hazard Symbols
  • Synonyms 2-Naphthalenol,5,6,7,8-tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, (5R-cis)-;Lasofoxifene;(5R,6S)-5,6,7,8-Tetrahydro-6-phenyl-5-(4-(2-(1-pyrrolidinyl)ethoxy)phenyl)-2-naphthalenol;
  • PSA 32.70000
  • LogP 5.66660

Synthetic route

1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine
5879-98-1

1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -50 - 0℃; for 3h;80%
With boron tribromide In dichloromethane74%
With boron tribromide In dichloromethane74%
7-methoxylasofoxifene

7-methoxylasofoxifene

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
Stage #1: 7-methoxylasofoxifene With boron tribromide In dichloromethane at -78 - 0℃; for 2h;
Stage #2: With water; sodium hydrogencarbonate In dichloromethane		76%
1-[2-(4-bromophenoxy)ethyl]pyrrolidine
1081-73-8

1-[2-(4-bromophenoxy)ethyl]pyrrolidine

n-BuU

n-BuU

6-methoxy-3,4-dihydro-1(2H)-naphthalenone
1078-19-9

6-methoxy-3,4-dihydro-1(2H)-naphthalenone

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
CeCl3 In tetrahydrofuran; hydrogenchloride; diethyl ether57%
CeCl3 In tetrahydrofuran; hydrogenchloride; diethyl ether57%
...Expand
lasofoxifene

lasofoxifene

lasofoxifene
180916-16-9

lasofoxifene

Butyric acid (5S,6R)-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalen-2-yl ester

Butyric acid (5S,6R)-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalen-2-yl ester

A

(5S,6R)-6-Phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalen-2-ol

(5S,6R)-6-Phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalen-2-ol

B

lasofoxifene
180916-16-9

lasofoxifene

C

Butyric acid (5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalen-2-yl ester

Butyric acid (5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalen-2-yl ester

Conditions
ConditionsYield
With Lipase (Mucor Miehei) In phosphate buffer at 20℃; pH=7; Hydrolysis; enzymatic resolution;
...Expand
lasofoxifene

lasofoxifene

AcX

AcX

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: Lipase (Mucor Miehei) / aq. phosphate buffer / 20 °C / pH 7
View Scheme
nafoxidine
1845-11-0

nafoxidine

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2 / Pd(OH)2/C
2: BBr3
View Scheme
(1RS,2SR)-1-(4-[2-pyrrolidinoethoxy]phenyl)-2-phenyl-6-methoxy-1,2,3,4-tetrahydronaphthalene

(1RS,2SR)-1-(4-[2-pyrrolidinoethoxy]phenyl)-2-phenyl-6-methoxy-1,2,3,4-tetrahydronaphthalene

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: BBr3
View Scheme
6-benzyloxy-1-[4-(2-(pyrrolidin-1-yl)ethoxy)phenyl]-3,4-dihydronaphthalen-2(1H) -one

6-benzyloxy-1-[4-(2-(pyrrolidin-1-yl)ethoxy)phenyl]-3,4-dihydronaphthalen-2(1H) -one

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: cerium(III) chloride / tetrahydrofuran / 1.5 h / -10 - 0 °C / Inert atmosphere
1.2: 2 h / -10 - -5 °C
2.1: methanol
3.1: hydrogen; 5%-palladium/activated carbon / methanol; ethanol / 10 h / 50 °C / 7600.51 Torr / Autoclave
View Scheme
6-benzyloxy-2-phenyl-1-{4-[2-(pyrrolin-1-yl)ethoxy]phenyl}-3,4-dihydronaphthalene

6-benzyloxy-2-phenyl-1-{4-[2-(pyrrolin-1-yl)ethoxy]phenyl}-3,4-dihydronaphthalene

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol
2: hydrogen; 5%-palladium/activated carbon / methanol; ethanol / 10 h / 50 °C / 7600.51 Torr / Autoclave
View Scheme
C35H35NO2*C4H6O6

C35H35NO2*C4H6O6

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol; ethanol at 50℃; under 7600.51 Torr; for 10h; Autoclave;
1-[2-(4-bromophenoxy)ethyl]pyrrolidine
1081-73-8

1-[2-(4-bromophenoxy)ethyl]pyrrolidine

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: magnesium / tetrahydrofuran / 20 - 30 °C / Inert atmosphere
1.2: 1 h / Reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
3.1: cerium(III) chloride / tetrahydrofuran / 1.5 h / -10 - 0 °C / Inert atmosphere
3.2: 2 h / -10 - -5 °C
4.1: methanol
5.1: hydrogen; 5%-palladium/activated carbon / methanol; ethanol / 10 h / 50 °C / 7600.51 Torr / Autoclave
View Scheme
6-benzyloxy-1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-3,4-dihydronaphthalene

6-benzyloxy-1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-3,4-dihydronaphthalene

lasofoxifene
180916-16-9

lasofoxifene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
2.1: cerium(III) chloride / tetrahydrofuran / 1.5 h / -10 - 0 °C / Inert atmosphere
2.2: 2 h / -10 - -5 °C
3.1: methanol
4.1: hydrogen; 5%-palladium/activated carbon / methanol; ethanol / 10 h / 50 °C / 7600.51 Torr / Autoclave
View Scheme
D-tartaric acid
147-71-7

D-tartaric acid

lasofoxifene
180916-16-9

lasofoxifene

Lasofoxifene tartrate
190791-29-8

Lasofoxifene tartrate

Conditions
ConditionsYield
In ethanol for 0.0833333h; Reflux;50%
1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine hydrochloride
1847-63-8

1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine hydrochloride

lasofoxifene
180916-16-9

lasofoxifene

1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine
5879-98-1

1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine

Conditions
ConditionsYield
palladium dihydroxide In ethanol863 mg (93%)
palladium dihydroxide In ethanol863 mg (93%)
lasofoxifene
180916-16-9

lasofoxifene

C34H42BNO3

C34H42BNO3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / dichloromethane / 1 h / 0 - 20 °C
2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 120 °C / Microwave irradiation
View Scheme
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

lasofoxifene
180916-16-9

lasofoxifene

C29H30F3NO4S

C29H30F3NO4S

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 1h;0.15 g

Lasofoxifene Specification

The CAS register number of Lasofoxifene is 180916-16-9. It also can be called as (5R,6S)-5,6,7,8-Tetrahydro-6-phenyl-5-(4-(2-(1-pyrrolidinyl)ethoxy)phenyl)-2-naphthalenol and the IUPAC name about this chemical is (5R,6S)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol. The molecular formula about this chemical is C28H31NO2 and the molecular weight is 413.55. It belongs to the following product categories, such as Aromatics; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals and so on. This chemical can be used as a next-generation selective estrogen receptor modulator for treating disorders associated with increased bone turnover and osteopenia.

Physical properties about Lasofoxifene are: (1)ACD/LogP: 6.51; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 3; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 7; (6)Polar Surface Area: 21.7Å2; (7)Index of Refraction: 1.613; (8)Molar Refractivity: 125.14 cm3; (9)Molar Volume: 359.3 cm3; (10)Polarizability: 49.61x10-24cm3; (11)Surface Tension: 48.2 dyne/cm; (12)Enthalpy of Vaporization: 89 kJ/mol; (13)Boiling Point: 572.4 °C at 760 mmHg; (14)Vapour Pressure: 1.05E-13 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O(c1ccc(cc1)[C@@H]4c2ccc(O)cc2CC[C@@H]4c3ccccc3)CCN5CCCC5
(2)InChI: InChI=1/C28H31NO2/c30-24-11-15-27-23(20-24)10-14-26(21-6-2-1-3-7-21)28(27)22-8-12-25(13-9-22)31-19-18-29-16-4-5-17-29/h1-3,6-9,11-13,15,20,26,28,30H,4-5,10,14,16-19H2/t26-,28+/m1/s1
(3)InChIKey: GXESHMAMLJKROZ-IAPPQJPRBB
(4)Std. InChI: InChI=1S/C28H31NO2/c30-24-11-15-27-23(20-24)10-14-26(21-6-2-1-3-7-21)28(27)22-8-12-25(13-9-22)31-19-18-29-16-4-5-17-29/h1-3,6-9,11-13,15,20,26,28,30H,4-5,10,14,16-19H2/t26-,28+/m1/s1
(5)Std. InChIKey: GXESHMAMLJKROZ-IAPPQJPRSA-N

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