148043-73-6

Basic information

• Product Name: 4,4,5,5,5-Pentafluoro-1-pentanol
• Synonyms: 4,4,5,5,5-PENTAFLUOROPENTAN-1-OL;4,4,5,5,5-PENTAFLUOROPENTANOL;4,4,5,5,5-PENTAFLUORO-1-PENTANOL;Pentafluoropentanol;4,4,5,5,5-Pentafluoropentan-1-ol 96%;4,4,5,5,5-Pentafluoropentan-1-ol96%;4,4,5,5,5-Pentafluoro-1-pentanol ,97%;4,4,5,5,5-Pentafluoro-1-pentanol,95%
• CAS NO: 148043-73-6
• Molecular Formula: C₅H₇F₅O
• Molecular Weight: 178.1
• EINECS: 421-360-9
• Product Categories: Industrial/Fine Chemicals;Organic Fluorides;Alcohols;C2 to C6;Oxygen Compounds;Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 148043-73-6.mol

Chemical Properties

• Boiling Point: 62-64 °C35 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: Clear colorless/Liquid
• Density: 1.35 g/mL at 25 °C(lit.)
• Vapor Pressure: 78mmHg at 25°C
• Refractive Index: n20/D 1.33(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• PKA: 14.77±0.10(Predicted)
• CAS DataBase Reference: 4,4,5,5,5-Pentafluoro-1-pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5,5-Pentafluoro-1-pentanol(148043-73-6)
• EPA Substance Registry System: 4,4,5,5,5-Pentafluoro-1-pentanol(148043-73-6)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36-36/37/38
• Safety Statements: 26-36
• RIDADR: 1993
• WGK Germany: 2
• HazardClass: FLAMMABLE
• Hazardous Substances Data: 148043-73-6(Hazardous Substances Data)

Usage

Uses

Used in the Chemical Industry:
4,4,5,5,5-Pentafluoro-1-pentanol is used as a precursor in the preparation of chlorine-capped telechelic poly(methyl methacrylate)s. These polymers have a wide range of applications, including the production of high-performance materials for various industries such as automotive, aerospace, and electronics.
Used in the Pharmaceutical Industry:
4,4,5,5,5-Pentafluoro-1-pentanol serves as an intermediate in the synthesis of pentafluoropentane-1-thiol, which is an important chain in the development of anti-breast cancer agents. Its role in the pharmaceutical industry highlights its potential as a key component in the fight against breast cancer.

InChI:InChI=1/C5H7F5O/c6-4(7,2-1-3-11)5(8,9)10/h11H,1-3H2

Synthetic route

4,4,5,5,5-pentafluoro-2-iodopent-2-en-1-ol (172032-07-4) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With hydrogen; triethylamine; platinum(IV) oxide In ethyl acetate at 25℃; for 3h;	95%

4,4,5,5,5-pentafluoropentyl acetate (148043-72-5) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With sodium hydroxide for 1h; Heating;	92%

1,1,1,2,2-pentafluoropentane → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With Cumene hydroperoxide In isopropyl alcohol at 80℃; for 2h; Reagent/catalyst; Solvent; Temperature; Autoclave;	83.3%

4,4,5,5,5-pentafluoro-2-iodopentyl acetate (148043-71-4) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / azoisobutyronitrile (AIBN), Bu3SnH / 55 - 65 °C 2: 92 percent / aq. NaOH / 1 h / Heating View Scheme

tert-butyl methyl ether (1634-04-4) + 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol (757-06-2) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With hydrogen; triethylamine; palladium

4,4,5,5,5-pentafluoro-2-iodo-1-pentanol (757-06-2) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
With triethylamine; palladium In water; ethyl acetate
With 2,2'-azobis(isobutyronitrile); palladium diacetate at 60 - 70℃; Reagent/catalyst;
With hydrogen; triethylamine In acetonitrile at 50℃; under 15001.5 Torr; for 0.5h; Flow reactor;

4,4,5,5,5-pentafluoro-2-iodo-1-pentanol (757-06-2) + ethanolamine (141-43-5) → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
palladium In water

4,4,5,5,5-pentafluoro-2-penten-1-ol → 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6)

Conditions	Yield
platinum (IV) oxide In ethyl acetate
platinum (IV) oxide In ethyl acetate

methanesulfonyl chloride (124-63-0) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 1-methanesulfonyloxy-4,4,5,5,5-pentafluoropentane (252947-01-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3 - 12h; Product distribution / selectivity;	100%
With triethylamine In tetrahydrofuran at 0 - 20℃;	99%
With triethylamine In dichloromethane at 0℃; for 0.75h;	96%

thiobenzoic acid (98-91-9) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → thiobenzoic acid S-(4,4,5,5,5-pentafluoro-pentyl)ester (862700-61-6)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	99%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 17h;	75 g

5,10,15,20-tetrakis[2-fluoro-5-(chlorosulfonyl)phenyl]porphyrin + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 5,10,15,20-tetrakis[2-fluoro-5-(4,4,5,5,5-pentafluoropentyloxy)sulfonylphenyl]porphyrin

Conditions	Yield
In tetrahydrofuran; water at 5 - 20℃;	95%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 1,1,1,2,2-pentafluoro-5-chloro-n-pentane

Conditions	Yield
With thionyl chloride; triethylamine In dichloromethane at 0 - 20℃; Solvent; Reagent/catalyst;	95%
With thionyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 2h; Solvent; Reagent/catalyst;	95%

p-(chloromethyl)benzoyl chloride (876-08-4) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → C13H12ClF5O2 (1293408-08-8)

Conditions	Yield
With triethylamine In acetone at 10 - 20℃; for 2h; Inert atmosphere;	93%
With triethylamine In acetone at 10 - 20℃; for 2h; Inert atmosphere;	93%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) + molecular sieve supported p-toluenesulfonic acid → 4,4,5,5,5-pentafluoropentyl-4-methylbenzene sulphonate (209325-64-4)

Conditions	Yield
at 65℃; for 1h; Temperature; Microwave irradiation; Molecular sieve;	91%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) + thioacetic acid (507-09-5) → 1-(acetylsulfanyl)-4,4,5,5,5-pentafluoropentane (160598-75-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran 1.) 0 deg C, 30 min; 2.) 0 deg C, 30 min then 25 deg C, 1 h;	88%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → C11H10F5NO5S

Conditions	Yield
With dmap; triethylamine In dichloromethane at -10℃; for 1h; Concentration;	85%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 4,4,5,5,5-pentafluoropentanoic acid (3637-31-8)

Conditions	Yield
With Jones reagent In acetone at 0 - 20℃; for 1h;	82%
With sodium permanganate monohydrate; tetraethylammonium hydrogen sulphate In water at 65 - 75℃; for 6.5h; Large scale;	77%
With chromium(VI) oxide; acetic acid at 0 - 20℃; for 26h;	63%

5,10,15,20-tetrakis[2,6-difluoro-3-(chlorosulfonyl)phenyl]porphyrin + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 5,10,15,20-tetrakis[2,6-difluoro-3-(4,4,5,5,5-pentafluoropentyloxy)sulfonylphenyl]porphyrin

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 5 - 20℃;	82%

C34H52N2O9S + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → C39H57F5N2O9S

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; Mitsunobu reaction;	67%

4-[9-(N-t-butyloxycarbonylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 4-[9-(N-t-butyloxycarbonyl-N-4,4,5,5,5-pentafluoropentylaminosulfonylamino)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃;	67%

p-toluenesulfonyl chloride (98-59-9) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 4,4,5,5,5-pentafluoropentyl-4-methylbenzene sulphonate (209325-64-4)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 24h;	61%
With pyridine at 0 - 20℃;	53%
With pyridine at 0 - 20℃;	53%
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane
With triethylamine In dichloromethane at 20℃; for 18h;

Gly-Ni-(S)-2-[N-(N-benzylpropyl)amino]benzophenone + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → C32H30F5N3NiO3 + C32H30F5N3NiO3

Conditions	Yield
With cyanomethylenetributyl-phosphorane at 105℃; Inert atmosphere; Sealed tube; diastereoselective reaction;	A 50% B n/a

Gly-Ni-(S)-2-[N-(N-benzylpropyl)amino]benzophenone + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → C32H30F5N3NiO3 + C33H32F5N3NiO3

Conditions	Yield
With cyanomethylenetributyl-phosphorane at 105℃; Mitsunobu Displacement; Sealed tube; Inert atmosphere; diastereoselective reaction;	A 50% B n/a

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 1,1,1,2,2-pentafluoro-5-iodo-pentane (151556-31-9)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 1.5h;	45%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 1.5h; Inert atmosphere;	45%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane for 2.5h;
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: sodium iodide / acetone / 12 h / Reflux View Scheme
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;

{(R)-2-[3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-5-piperazin-1-yl-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (1308375-93-0) + 4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → (R)-tert-butyl-(2-(3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-5-(4-(4,4,5,5,5-pentafluoropentyl)-piperazin-1-yl)-2,3-dihydropyrimidin-1(6H)-yl)-1-phenylethyl)carbamate (1308380-96-2)

Conditions	Yield
With potassium carbonate; methanesulfonyl chloride; triethylamine In dichloromethane; acetonitrile at 80℃; for 7h;	21%

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) + 1,1'-carbonyldiimidazole (530-62-1) → imidazole-1-carboxylic acid 4,4,5,5,5-pentafluoro-pentyl ester

Conditions	Yield
In tetrahydrofuran at 20℃;
In tetrahydrofuran at 20℃; for 0.5h;

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfanyl)octyl]thiochroman

Conditions	Yield
Multi-step reaction with 3 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 76 percent / sodium methoxide / methanol; tetrahydrofuran / 12 h / 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfanyl)octyl]thiochroman

Conditions	Yield
Multi-step reaction with 3 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 16 percent / sodium methoxide / methanol; tetrahydrofuran / 12 h / 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfanyl)octyl]thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 76 percent / sodium methoxide / methanol; tetrahydrofuran / 12 h / 20 °C 4: boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfanyl)octyl]chroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 59 percent / sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: hydrogen chloride / methanol / 0.25 h / 60 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[8-(4,4,5,5,5-pentafluoropentylsulfinyl)octyl]chroman-7-ol

Conditions	Yield
Multi-step reaction with 5 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 59 percent / sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: hydrogen chloride / methanol / 0.25 h / 60 °C 5: oxone(R) / tetrahydrofuran; H2O / 0.17 h / 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → (3S,4S)-3-(4-Hydroxy-phenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoro-pentylsulfanyl)-nonyl]-thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: sodium methoxide / methanol; tetrahydrofuran / 12 h / 20 °C 4: boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → (3R,4R)-3-(4-Hydroxy-phenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoro-pentylsulfanyl)-nonyl]-thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 79 percent / sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: 74 percent / boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

4,4,5,5,5-pentafluorpentan-1-ol (148043-73-6) → 3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]thiochroman-7-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 33.9 g / triethylamine / CH2Cl2 / 0 - 20 °C 2: 51 percent / acetone / 12 h / 20 °C 3: 11 percent / sodium methoxide / methanol; tetrahydrofuran / 20 °C 4: boron tribromide / CH2Cl2 / -78 - 20 °C View Scheme

Upstream product

• 1634-04-4 tert-butyl methyl ether 
• 757-06-2 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol 
• 172032-07-4 4,4,5,5,5-pentafluoro-2-iodopent-2-en-1-ol 
• 148043-72-5 4,4,5,5,5-pentafluoropentyl acetate 
• 141-43-5 ethanolamine 
• 148043-71-4 4,4,5,5,5-pentafluoro-2-iodopentyl acetate 

Downstream Products

• 3637-31-8 4,4,5,5,5-pentafluoropentanoic acid 
• 101615-36-5 (4,4,5,5,5-pentafluoropentyl)iminothiocarbamate 4-methylbenzenesulfonate 
• 1332392-73-0 (4-(benzyloxy)butyl)(4,4,5,5,5-pentafluoropentyl)sulfane 
• 380-60-9 3,3,4,4,4-pentafluorobutanoic acid 
• 107-92-6 butyric acid 
• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 
• 129453-61-8 fulvestrant 
• 209325-64-4 4,4,5,5,5-pentafluoropentyl-4-methylbenzene sulphonate 

Relevant articles and documents

Laboratory scale preparation of 4,4,5,5,5-pentafluoropentan-1-thiol: An important chain of antibreast cancer agents

Quantitative free radical addition of perfluoroethyl iodide to propargyl alcohol in the presence of sodium hydrosulfite gave E/Z-2-iodo-4,4,5,5,5-pentafluoro-2-penten-1-ols, which were converted to 4,4,5,5,5-pentafluoropentan-1-ol in one step in excellent yield by catalytic hydrogenation over platinum oxide in the presence of triethylamine. 4,4,5,5,5-Pentafluoropentan-1-thiol was obtained in good yield via modified Mitsunobu reaction of the alcohol.

Method for preparing 4, 4, 5, 5, 5-pentafluoropentanol

The invention discloses a method for preparing 4, 4, 5, 5, 5-pentafluoropentanol. The 4, 4, 5, 5, 5-pentafluoropentanol is obtained by one-step method for catalytic oxidation of 1, 1, 1, 2, 2-pentafluoropropane in the presence of a supported noble metal composite catalyst, a solvent and an oxidizing agent, wherein the solvent is water, acetonitrile, isopropanol, dimethylformamide and N-methyl pyrrolidone, the oxidizing agent is an organic peroxide and comprises cumene hydroperoxide, tert-butyl hydroperoxide, acetyl peroxide, benzoyl peroxide, dibenzoyl peroxide, cyclohexanone peroxide, iodosobenzene (PhIO) and m-chloroperbenzoic acid, the mass ratio of the 1, 1, 1, 2, 2- perfluoropropane to the catalyst to the solvent to the oxidizing agent is 1: (0.01-0.1): (0.5-2): (0.05-0.5). The methodfor preparing the 4, 4, 5, 5, 5-pentafluoropentanol, disclosed by the invention, has the advantages of simple reaction operation, high selectivity and mild reaction conditions.

Visible-Light-Mediated Iodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate

Two efficient continuous flow iodoperfluoroalkylation methods are described: using 0.05 mol % perylene diimide (PDI) photocatalyst under 450 nm irradiation or substoichiometric triethylamine under 405 nm irradiation. These methods enable dramatically elevated productivity versus batch processes. The triethylamine-mediated method is explored mechanistically and in substrate scope. The gram-scale synthesis of an active pharmaceutical ingredient side chain is also reported in flow, via a photochemical iodoperfluoroalkylation followed by hydrogenolysis.

Preparation method of pentafluoropentanol

The invention discloses a preparation method of pentafluoropentanol. The preparation method comprises the following steps: firstly, synthetic reaction: carrying out a reaction between propenol and pentafluoroethyliodide under the action of a free radical initiator to generate 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol; secondly, hydrogenated dehalogenation reaction: carrying out the hydrogenated dehalogenation reaction under the action of the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol to generate a pentafluoropentanol product. The invention provides the preparation method of the pentafluoropentanol. The pentafluoroethyliodide and the propenol serving the raw material undergo free radical reaction to generate the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol, and the 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol undergoes dehalogenation reaction under the action of a reducing agent to generate the pentafluoropentanol. The method is high in reaction yield and easy for industrial production; in addition, the purity of the product is higher than 99 percent.

Process for preparing pentafluoropentanol

4,4,5,5,5-Pentafluoro-1-pentanol is prepared in a particularly advantageous manner from perfluoroethyl iodide by initially adding perfluoroethyl iodide in the presence of a radical initiator which does not carry any acyl groups to allyl alcohol and then hydrogenolytically dehalogenating the resulting 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol in the presence of a catalyst, an acid binder and a diluent.

11β-substituted 14,17-ethanoestratrienes, process for their production and their use as pharmaceutical agents

The invention relates to 11 β-substituted 14,17-ethanoestratrienes of the general formula 1 STR1 where R 1, R 2 and R 3 are defined in the specification. The compound have antiestrogenic activity and are, therefore, useful for the treatment of estrogen dependent disorders.

Synthesis of Amino Acids with Modified Principal Properties 1. Amino Acids with Fluorinated Side Chains

The synthesis and characterization of chiral fluorinated analogues of norvaline and norleucine from commercially available starting materials are presented.Full experimental details for the synthesis of the following amino acids are given: (S)-4,4-difluoronorvaline, (S)-4,4,5,5,5-pentafluoronorvaline, (S)-5,5-difluoronorleucine, (S)-5,5,6,6,6-pentafluoronorleucine, and (S)-4,4,5,5,6,6,6-heptafluoronorleucine.These compounds were prepared with a view to obtaining new amino acids which possess physical and chemical properties so that their principal properties would be outside the range of variation of hitherto known amino acids.The principal properties are determined as latent variables in principal component analysis of molecular property descriptors.Two of the fluorinated amino acids, (S)-5,5,6,6,6-pentafluoronorleucine and (S)-4,4,5,5,6,6,6-heptafluoronorleucine were found to have principal properties outside the variation of previously characterized natural and synthetic amino acids.The principal properties, z parameters, for the five new fluorinated amino acids are given.