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Merck
CN

761060

Sigma-Aldrich

(Tributylphosphoranylidene)acetonitrile

97%

别名:

(Cyanomethylene)tributylphosphorane

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About This Item

经验公式(希尔记法):
C14H28NP
分子量:
241.35
UNSPSC代码:
12352000
NACRES:
NA.22

质量水平

检测方案

97%

形式

liquid

折射率

n20/D 1.500 (lit.)

密度

0.921 g/mL at 25 °C

储存温度

2-8°C

InChI

1S/C14H28NP/c1-4-7-11-16(14-10-15,12-8-5-2)13-9-6-3/h14H,4-9,11-13H2,1-3H3

InChI key

OZMLUMPWPFZWTP-UHFFFAOYSA-N

一般描述

(Tributylphosphoranylidene)acetonitrile or cyanomethylenetrimethylphosphorane (Bu3P=CHCN) is a Wittig reagent employed in the transformation of the carbonyl compounds, including aldehydes, esters, and lactones into the corresponding unsaturated nitriles.

应用

(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.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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(Tributylphosphoranylidene) acetonitrile
Wyatt, Peter B
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides
Tsunoda T, et al.
Tetrahedron Letters, 41(2), 235-237 (2000)
Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine
Tsunoda T, et al.
Tetrahedron Letters, 37(14), 2463-2466 (1996)

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