Pyrrolidine,2-[diphenyl[(trimethylsilyl)oxy]methyl]-,(2R)- supplier

Name
Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)-
EINECS
CAS No. 943757-71-9
Density 1.021 g/cm³
Solubility
Melting Point
Formula C₂₀H₂₇NOSi
Boiling Point 412.7 °C at 760 mmHg
Molecular Weight 325.526
Flash Point 203.4 °C
Transport Information
Appearance
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms (diphenyl(trimethylsilyloxy)methyl)pyrrolidine;(2R)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine;diphenyl prolinol silyl ether;(2R)-2-[Diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine;(R)-2-[Diphenyl(trimethylsilanyloxy)methyl]pyrrolidine;(R)-α,α-Diphenylprolinol trimethylsilyl ether;
PSA 21.26000
LogP 4.86250

Synthetic route

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 837-95-6
2-nitro-4-(trifluoromethyl)benzenesulfonyl chloride

: C27H29F3N2O5SSi

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	95%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: (R)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((4-nitrophenyl)sulfonyl)pyrrolidine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	94%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 162010-78-8
4-chlorosulfonyl-3-nitrobenzoic acid methyl ester

: C28H32N2O7SSi

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	93%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: (R)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((2-nitrophenyl)sulfonyl)pyrrolidine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	92%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 121-51-7
3-nitrobenzenesulphonyl chloride

: (R)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((3-nitrophenyl)sulfonyl)pyrrolidine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	91%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 18092-54-1
4-methoxy-2-nitrobenzenesulfonyl chloride

: C27H32N2O6SSi

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	90%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 4533-96-4
4-chloro-2-nitrobenzenesulfonyl chloride

: C26H29ClN2O5SSi

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	88%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 264224-82-0
(E)-4-methyl-2-(2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631165-98-4
(-)-(E)-ethyl 3-((2S,3R,4R)-2,6-dimethyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-4-methyl-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	87%

...Expand

: 568586-10-7
4-fluoro-2-nitrobenzene-1-sulfonyl chloride

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: C26H29FN2O5SSi

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	85%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 61131-72-4
trans-4-bromo-2-(2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631165-96-2
(-)-(E)-ethyl 3-((2S,3R,4R)-6-bromo-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; trans-4-bromo-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	83%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 1308249-79-7
4-fluoro-2-((E)-2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631165-94-0
(-)-(E)-ethyl 3-((2S,3R,4R)-6-fluoro-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 4-fluoro-2-((E)-2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	82%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 61131-68-8
(E)-4-chloro-2-(2-nitroethenyl)phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631165-95-1
(-)-(E)-ethyl 3-((2S,3R,4R)-6-chloro-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-4-chloro-2-(2-nitroethenyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	82%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 1310493-82-3
2,4-chloro-2-((E)-2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631165-97-3
(-)-(E)-ethyl 3-((2S,3R,4R)-6,8-dichloro-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2,4-chloro-2-((E)-2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	82%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 35467-98-2
(E)-4-methoxy-2-(2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631165-99-5
(-)-(E)-ethyl 3-((2S,3R,4R)-6-methoxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-4-methoxy-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	82%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 2-((1E)-2-nitrovinyl)-4-nitrophenol

: 1631166-02-3
(-)-(E)-ethyl 3-((2S,3R,4R)-8-hydroxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; acetaldehyde; 2-((1E)-2-nitrovinyl)-4-nitrophenol In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	80%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 3156-43-2
2-[(E)-2-nitrovinyl]phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631165-93-9
(-)-(E)-ethyl 3-((2S,3R,4R)-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2-[(E)-2-nitrovinyl]phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h; Reagent/catalyst; Concentration; Temperature; Solvent;	80%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 96853-34-8
(E)-5-methoxy-2-(2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631166-00-1
(-)-(E)-ethyl 3-((2S,3R,4R)-7-methoxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-5-methoxy-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	80%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 3156-43-2
2-[(E)-2-nitrovinyl]phenol

: 75-07-0
acetaldehyde

: 1631165-92-8
(-)-(2S,3R,4R)-2-methyl-4-(nitromethyl)chroman-3-carbaldehyde

Conditions

Conditions	Yield
In chloroform at -40 - -5℃; for 3.25h;	80%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 1986-06-7, 141849-32-3
(E)-2-methoxy-6-(2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631166-01-2
(-)-(E)-ethyl 3-((2S,3R,4R)-8-methoxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-2-methoxy-6-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	75%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 1308250-94-3
(E)-3-(2-nitrovinyl)benzene-1,2-diol

: 75-07-0
acetaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1631166-02-3
(-)-(E)-ethyl 3-((2S,3R,4R)-8-hydroxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-3-(2-nitrovinyl)benzene-1,2-diol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	75%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 3156-43-2
2-[(E)-2-nitrovinyl]phenol

: 75-07-0
acetaldehyde

: 1631165-85-9
(-)-((2S,3S,4R)-2-methyl-4-(nitromethyl)chroman-3-yl)methanol

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2-[(E)-2-nitrovinyl]phenol; acetaldehyde In chloroform at -40 - -5℃; for 3.25h; Stage #2: With methanol; sodium tetrahydroborate In chloroform at 0℃; for 1h;	75%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 20345-61-3
ethyl 2-diethoxyphosphinoylacrylate

: 3156-43-2
2-[(E)-2-nitrovinyl]phenol

: 75-07-0
acetaldehyde

: 1631166-04-5
(-)-(6S,6aR,10S,10aR)-ethyl 6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2-[(E)-2-nitrovinyl]phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl 2-diethoxyphosphinoylacrylate With caesium carbonate In dichloromethane at 0℃; for 6h; Inert atmosphere; Stage #3: With ethanol In dichloromethane at 0 - 20℃; for 2h;	75%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 590-86-3
isovaleraldehyde

: C25H35NOSi

Conditions

Conditions	Yield
In dimethylsulfoxide-d6	75%

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 20345-61-3
ethyl 2-diethoxyphosphinoylacrylate

: 1308250-94-3
(E)-3-(2-nitrovinyl)benzene-1,2-diol

: 75-07-0
acetaldehyde

: 1631166-07-8
(-)-(6S,6aR,10S,10aR)-ethyl 4-hydroxy-6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-3-(2-nitrovinyl)benzene-1,2-diol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl 2-diethoxyphosphinoylacrylate With caesium carbonate In dichloromethane at 0℃; for 6h; Inert atmosphere; Stage #3: With ethanol In dichloromethane at 0 - 20℃; for 2h;	72%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 20345-61-3
ethyl 2-diethoxyphosphinoylacrylate

: 1310493-82-3
2,4-chloro-2-((E)-2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1631166-06-7
(-)-(6S,6aR,10S,10aR)-ethyl 2,4-dichloro-6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2,4-chloro-2-((E)-2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl 2-diethoxyphosphinoylacrylate With caesium carbonate In dichloromethane at 0℃; for 6h; Inert atmosphere; Stage #3: With ethanol In dichloromethane at 0 - 20℃; for 2h;	70%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 20345-61-3
ethyl 2-diethoxyphosphinoylacrylate

: 61131-72-4
trans-4-bromo-2-(2-nitrovinyl)phenol

: 75-07-0
acetaldehyde

: 1631166-05-6
(-)-(6S,6aR,10S,10aR)-ethyl 2-bromo-6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate

Conditions

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; trans-4-bromo-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl 2-diethoxyphosphinoylacrylate With caesium carbonate In dichloromethane at 0℃; for 6h; Inert atmosphere; Stage #3: With ethanol In dichloromethane at 0 - 20℃; for 2h;	67%

...Expand

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 39221-06-2
1-nitroethanol

: 24680-50-0, 71277-11-7, 1963-36-6
4-methoxy-trans-cinnamaldehyde

: (4R,5R)-4-(2-methoxyphenyl)-5-nitrotetrahydro-2H-pyran-2-ol

Conditions

Conditions	Yield
With benzoic acid In methanol at 40℃; for 10h; Inert atmosphere;	51%

...Expand

: 5153-67-3
nitrostyrene

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 75-07-0
acetaldehyde

A: 934269-53-1
(3R)-4-nitro-3-phenylbutanal

B: C14H15NO3

Conditions

Conditions	Yield
In chloroform at -40 - -5℃; for 96h;	A 25% B 25%

...Expand

: 5153-67-3
nitrostyrene

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: 23941-84-6
5-formy-1,3,6-trimethyluracil

: (5R,6R,7R)-5-((R)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-1,3-dimethyl-6-nitro-7-phenyl-5,6,7,8-tetrahydroquinazoline-2,4(1H,3H)-dione

Conditions

Conditions	Yield
In dichloromethane at 25℃; for 24h; Inert atmosphere;	18%

...Expand

: 5153-67-3
nitrostyrene

: 943757-71-9
(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine

: C8H7NO2*C20H27NOSi

Conditions

Conditions	Yield
In methanol for 0.166667h;

Pyrrolidine,2-[diphenyl[(trimethylsilyl)oxy]methyl]-,(2R)- Specification

The Pyrrolidine,2-[diphenyl[(trimethylsilyl)oxy]methyl]-,(2R)-, with the CAS registry number 943757-71-9, has the systematic name of (2R)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine. It is also called (R)-α,α-Diphenylprolinol trimethylsilyl ether. And the molecular formula of this chemical is C₂₀H₂₇NOSi.

The physical properties of Pyrrolidine,2-[diphenyl[(trimethylsilyl)oxy]methyl]-,(2R)- are as following: (1)ACD/LogP: 5.29; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.2; (4)ACD/LogD (pH 7.4): 2.44; (5)ACD/BCF (pH 5.5): 4.97; (6)ACD/BCF (pH 7.4): 8.62; (7)ACD/KOC (pH 5.5): 14.46; (8)ACD/KOC (pH 7.4): 25.08; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 12.47 Å²; (13)Index of Refraction: 1.535; (14)Molar Refractivity: 99.29 cm³; (15)Molar Volume: 318.6 cm³; (16)Polarizability: 39.36×10^-24cm³; (17)Surface Tension: 33.8 dyne/cm; (18)Density: 1.021 g/cm³; (19)Flash Point: 203.4 °C; (20)Enthalpy of Vaporization: 66.54 kJ/mol; (21)Boiling Point: 412.7 °C at 760 mmHg; (22)Vapour Pressure: 5.06E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O([Si](C)(C)C)C(c1ccccc1)(c2ccccc2)[C@@H]3NCCC3
(2)InChI: InChI=1/C20H27NOSi/c1-23(2,3)22-20(19-15-10-16-21-19,17-11-6-4-7-12-17)18-13-8-5-9-14-18/h4-9,11-14,19,21H,10,15-16H2,1-3H3/t19-/m1/s1
(3)InChIKey: RSUHWMSTWSSNOW-LJQANCHMBE

Product Name

Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)-

Synthetic route

Pyrrolidine,2-[diphenyl[(trimethylsilyl)oxy]methyl]-,(2R)- Specification

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