157141-27-0 Usage
Uses
(Tributylphosphoranylidene)acetonitrile can be utilized as a reagent in the: Stereoselective synthesis of skytanthine and other O- and N-containing heterocycles by Mitsunobu intramolecular cycloalkylation.Wittig olefination of esters, lactones, N-Boc lactam, and cyclic imide to corresponding Wittig products.
General Description
(Tributylphosphoranylidene)acetonitrile is a stabilized trialkylphosphorane that can act as a substitute to the diethyl azodicarboxylate and triphenylphosphine (DEAD-TPP) system for Mitsunobu reaction between nucleophiles (HA) and alcohols (ROH) to form RA. It is highly useful when the pKa of the nucleophiles are higher than 11.
Check Digit Verification of cas no
The CAS Registry Mumber 157141-27-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,7,1,4 and 1 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 157141-27:
(8*1)+(7*5)+(6*7)+(5*1)+(4*4)+(3*1)+(2*2)+(1*7)=120
120 % 10 = 0
So 157141-27-0 is a valid CAS Registry Number.
InChI:InChI=1/C14H28NP/c1-4-7-11-16(14-10-15,12-8-5-2)13-9-6-3/h14H,4-9,11-13H2,1-3H3
157141-27-0Relevant articles and documents
Preparation of (cyanomethylene)tributylphosphorane: A new mitsunobu-type reagent
Sakamoto, Izumi,Nishii, Takeshi,Ozaki, Fumie,Kaku, Hiroto,Tanaka, Masami,Tsunoda, Tetsuto
, p. 1508 - 1509 (2005)
(Cyanomethylene)tributylphosphorane (CMBP), which promoted the alkylation of various nucleophiles (HA) with alcohols (ROH) to give RA (Mitsunobu-type reaction), was prepared in two steps starting from chloroacetonitrile.
Novel reactivity of stabilized methylenetributylphosphorane: A new mitsunobu reagent
Tsunoda, Tetsuto,Ozaki, Fumie,Ito, Sho
, p. 5081 - 5082 (2007/10/02)
Cyanomethylenetributylphosphorane was shown to mediate the direct condensation of alcohols with O- and N-nucleophiles. A secondary alcohol, 2- octanol, reacted satisfactorily with Walden inversion of its carbinyl carbon.
