194233-66-4

Basic information

• Product Name: TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-N
• Synonyms: TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-N;trans-3-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-1,3-butadien-1-amine 90%;trans-3-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-1,3-butadiene-1-amine
• CAS NO: 194233-66-4
• Molecular Formula: C₁₂H₂₅NOSi
• Molecular Weight: 227.421
• Product Categories: Amines;C11 to C38;Nitrogen Compounds
• Mol File: 194233-66-4.mol

Chemical Properties

• Boiling Point: 234 °C(lit.)
• Flash Point: 200 °F
• Appearance: /
• Density: 0.878 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0429mmHg at 25°C
• Refractive Index: n20/D 1.493(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-N(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-N(194233-66-4)
• EPA Substance Registry System: TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-N(194233-66-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 194233-66-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-N is used as a protecting group in organic synthesis for the purpose of blocking reactive functional groups, thereby preventing unwanted side reactions and facilitating the selective formation of desired products.
Used in the Synthesis of Organic Compounds and Materials:
As an intermediate in the synthesis of various organic compounds and materials, TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-N is used to create new compounds with specific properties, leveraging the reactivity of the siloxy and tert-butyldimethylsilyloxy groups in a variety of chemical reactions.
Used in Chemical Research:
In the field of chemical research, TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-N is employed as a versatile building block to explore novel chemical reactions and pathways, contributing to the advancement of organic chemistry and materials science.

InChI:InChI=1/C12H25NOSi/c1-11(9-10-13(5)6)14-15(7,8)12(2,3)4/h9-10H,1H2,2-8H3/b10-9+

Upstream product

• 2802-08-6 (E)-4-(dimethylamino)but-3-en-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 224578-95-4 5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-3a,4-dihydro-isoindole-1,3-dione 

Relevant articles and documents

A formal total synthesis of dysidiolide

(Matrix presented) A formal total synthesis of the natural product dysidiolide is described. Starting from a Diels-Alder reaction between an enoate and a Rawal diene, the cyclohexenone 4 was synthesized. A subsequent stereospecific methyl cuprate addition established the desired trans configuration in the cyclohexane 3. Wacker oxidation of the pentenyl side chain to the diketone 17 followed by an intramolecular aldol condensation led to the bicyclic enone 2, a key intermediate in a recently reported synthesis of dysidiolide.

TRANSFORMING GROWTH FACTOR MODULATORS

The invention relates to compounds that are modulators of Transforming Growth Factor β (TGF β) and are useful for treating TGF β related diseases.

1-amino-3-siloxy-1,3-butadienes: Highly reactive dienes for the Diels- Alder reaction

1-Amino-3-siloxy-1,3-butadienes represent a novel class of heteroatom- containing dienes with several useful properties. These dienes can be prepared efficiently by deprotonation of readily available vinylogous amides with potassium hexamethylsilazide, followed by silylation of the corresponding potassium enolates. This protocol has been found to be quite general for the preparation of various dienes containing different silyl and amino groups. Amino siloxy dienes readily undergo [4 + 2] cycloadditions with a wide range of electron-deficient dienophiles. The reactions generally occur under very mild conditions to afford the corresponding [4 + 2] adducts in high yields and with complete regioselectivity. High endo selectivity is observed in the case of N-phenylmaleimide and methacrolein. Other cycloadducts are usually obtained as mixtures of endo/exo diastereomers. The cycloadducts are versatile synthetic intermediates. They can be subjected to deprotonation, reduction, and Wittig olefination without any hydrolysis or elimination. In addition, the elimination of the amino group can be cleanly accomplished under acidic conditions leading to the formation of enones. A variety of substituted cyclohexenones can be prepared by this procedure.