27943-47-1

Basic information

• Product Name: (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione
• CAS NO: 27943-47-1
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.1372
• Mol File: 27943-47-1.mol

Chemical Properties

• Boiling Point: 254.2°C at 760 mmHg
• Flash Point: 93.6°C
• Density: 1.264g/cm³
• Vapor Pressure: 0.0175mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione(27943-47-1)
• EPA Substance Registry System: (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione(27943-47-1)

Safety Data

• Hazardous Substances Data: 27943-47-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,4R)-bicyclo[2.2.1]heptane-2,5-dione is used as a building block in organic synthesis for creating more complex molecules. Its unique bicyclic structure allows for the formation of a variety of organic compounds with potential applications in different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione is used as a key intermediate in the development of new drugs. Its reactivity and structural features make it suitable for the synthesis of bioactive molecules with potential therapeutic properties.
Used as a Reagent in Chemical Reactions:
(1R,4R)-bicyclo[2.2.1]heptane-2,5-dione is also used as a reagent in various chemical reactions to introduce functional groups or modify existing molecules. This versatility allows chemists to explore its potential in the synthesis of new compounds with specific properties and applications.
Used in Medicine:
The unique structure and reactivity of (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione make it a promising candidate for the preparation of diverse organic compounds with potential applications in medicine. Its use in the synthesis of bioactive molecules can lead to the development of new therapeutic agents.
Used in Materials Science:
In materials science, (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione can be utilized in the development of new materials with specific properties. Its unique structure and reactivity can contribute to the creation of advanced materials for various applications, such as in electronics, coatings, or other industrial products.

Upstream product

• 930-30-3 cyclopent-2-enone 
• 69567-06-2 (N-methylanilino)prop-2-enenitrile 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 158666-09-2 formic acid 5-formyloxy-bicyclo[2.2.1]hept-2-yl ester 
• 5888-36-8 2,5-Norbornandiol 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 5888-36-8 (1R*,2R*,4R*,5R*)-bicyclo<2.2.1>heptane-2,5-diol 
• 5888-36-8 (rac)-(exo,exo)-bicyclo[2.2.1]heptane-2,5-diol 
• 5888-36-8 2-exo-5-endo-norbornanediol 

Downstream Products

• 128375-93-9 C₂₇H₃₆N₄ 
• 5888-36-8 (1R*,2R*,4R*,5R*)-bicyclo<2.2.1>heptane-2,5-diol 
• 128375-66-6 C₂₇H₃₄N₆O₄ 
• 57239-03-9 3,3,6,6-tetramethylbicyclo<2.2.1>heptane-2.5-dione 
• 876758-35-9 2,5-bis-(diphenyl-phosphinoyl)-bicyclo[2.2.1]hepta-2,5-diene 
• 876758-39-3 (1S,2S,4S,5S)-2,5-Bis-(diphenyl-phosphinoyl)-bicyclo[2.2.1]heptane 
• 125282-10-2 endo,endo-2,5-bis((p-tolylsulfonoxy)methyl)bicyclo<2.2.1>heptane 
• 145092-68-8 (S,S)-bicyclo<2.2.1>heptane-2,5-dione 
• 171065-84-2 2,5-diaminobicyclo[2.2.1]heptane 

Relevant articles and documents

Stereoselective coordination of C5-symmetric corannulene derivatives with an enantiomerically pure [RhI(nbd*)] metal complex

Catching the bowl! Enantiopure RhI dimethylnorbornadiene fragments selectively catch interconverting enantiomers of C5-sym- pentasubstituted corannulene derivatives in one bowl form and allow the observation and isolation of enantiopure metal-buckybowl complexes. A quantum mechanical model (see picture) predicts the mechanism of molecular dynamics and degree of stereoselective recognition.

A highly enantioselective catalyst for the asymmetric Nozaki-Hiyama-Kishi reaction of allylic and vinylic halides

Catalytic asymmetric addition of vinylic halides and trifiates to aldehydes, with useful levels of stereoinduction, has been achieved for the first time using the salentype ligand (S,S)-5 (see scheme; PMB=para-methoxybenzyl), which contains the novel endo

New Ligands with a Wide Bite Angle. Efficient Catalytic Activity in the Rh(I)-Catalyzed Hydroformylation of Olefins

The relevance of a new diphosphinite, which holds a natural bite angle around 120 deg in a catalyst complex, to the Rh(I)-catalyzed hydroformylation of certain olefins is examined, exhibiting a high turnover frequency (TOF) as compared with a typical 1,2-bis(diphenylphosphino)ethane with a bite angle around 85 deg.

Tandem-Michael addition of 1-cyanoenamines to cyclohexenones. A new access to bicyclo[2.2.2]octanones

Bicyclo[2.2.2]octane-2,5-diones 5 are easily obtained via tandem Michael addition of 2-(N-methylanilino)acrylonitrile (2) with deprotonated cyclohexenones I. The reaction is highly anti-stereoselective with respect to substituents on C-4 and C-5 of the cyclohexenone and is blocked by disubstitution on C-4. 6-Acylbicyclo[2.2.2]octan-2-ones 25 are obtained by tandem Michael addition of deprotonated 2-(N-methylanilino)but-2-enonitrile (18) with cyclohexenone and subsequent protonation or alkylation. Both reactions gave lower yields or even failed with cyclopentenone and cycloheptenone.

NEW STRATEGY IN THE STEREOCONTROLLED SYNTHESIS OF THE SPIRO KETAL SUBUNIT OF MILBEMYCINS

A double Baeyer-Villiger oxidation of bicyclo heptane-2,5-dione and a stereocontrolled alkylation of the dianion derived from 4-pentyn-2-ol are the salient features of a new strategy in the stereocontrolled synthesis of the spiroketal moiety of milbemycins.