76402-80-7

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dihydro-benzo[b]oxepine is used as a key intermediate in the synthesis of pharmaceutical compounds for its ability to contribute to the development of drugs with potent therapeutic effects. Its role in creating antipsychotic and antidepressant medications underscores its importance in mental health treatment.
Used in Medicinal Chemistry:
As a precursor for the synthesis of other biologically active molecules, 2,5-Dihydro-benzo[b]oxepine is utilized in medicinal chemistry to explore and produce new compounds with potential therapeutic applications, thereby expanding the scope of available treatments for various health conditions.
The synthesis of 2,5-Dihydro-benzo[b]oxepine is typically achieved through a series of chemical reactions involving benzoxepine and an array of reagents and catalysts, highlighting the compound's synthetic accessibility and its potential for further chemical modification to meet specific pharmaceutical needs.

Upstream product

• 3383-05-9 allyl 2-allylphenyl ether 
• 1745-81-9 o-Allylphenol 
• 76402-78-3 trans-1,5,8,8a-tetrahydronaphthalen-4a(4H)-ol 

Relevant academic research and scientific papers

Activation of olefin metathesis complexes containing unsymmetrical unsaturated N-heterocyclic carbenes by copper and gold transmetalation

The activation of ruthenium-indenylidene complexes containing two unsymmetrical unsaturated N-heterocyclic carbenes (u2-NHCs) by a transmetalation process is reported. The use of copper(i) or gold(i) chlorides promotes the rapid trapping of one NHC ligand, which releases the catalytically active Ru-species. Impressive initiation rates with full-conversions are observed within one minute. This practical protocol demonstrates excellent catalytic performances in various ring-closing metathesis (RCM) and self-metathesis (SM) reactions.

Design of bis-NHC Ru-complexes featuring diarylmethylene N-substituents for olefin metathesis

New ruthenium indenylidene complexes containing N-heterocyclic carbene (NHC) ligands were synthesized and evaluated in olefin metathesis. The presence of two symmetrical saturated NHCs featuring N-diarylmethylene fragments (R= H, OMe or F) led to robust ruthenium precatalysts with a good latency. A kinetic study was investigated showing that a thermal stimulus (>60 °C) is required to reach an efficient catalytic initiation. Interestingly, a slight electronic effect was observed depending on the presence of an electron-donating or –withdrawing group within the diarylmethylene moiety. These complexes showed good activity at 1 mol% of catalyst loading in selected ring-closing metathesis (RCM) and cross-metathesis (CM) transformations.

Nitrogen-coordination-containing ruthenium carbene catalyst and preparation method and application thereof

The present invention discloses a nitrogen-coordination-containing ruthenium carbene catalyst and a preparation method and application thereof. The nitrogen-coordination-containing ruthenium carbene catalyst is characterized by being shown in a formula (I

A pH-controlled recyclable indolinooxazolidine tagged N-heterocyclic carbene Ru catalyst for olefin metathesis

An indolinooxazolidine tagged N-heterocyclic carbene Ru olefin metathesis catalyst was synthesized and the molecular structure of this new Ru complex was determined by single crystal X-ray diffraction. This complex is a homogeneous catalyst and can be recovered by controlling the polarity of the indolinooxazolidine tag. Under acidic conditions the indolinooxazolidine tag exists as an open protonated form and under basic conditions the tag is in a closed form. The distribution of this catalyst in a two-phase system can be controlled by simply changing the pH, making the recovery of this catalyst easily obtainable.

Highly efficient nitrogen chelated ruthenium carbene metathesis catalysts

A series of nitrogen chelated ruthenium carbene metathesis catalysts containing an N-heterocyclic carbene (NHC) and a carbonyl group have been developed and their catalytic activities for olefin metathesis reactions were investigated. The X-ray structure of the [(H2IMes)(Cl)2Ru]C(H)CH2[p-F(C6H3)NC(CF3)(C(O)OCH2CH3)] complex shows that the carbonyl oxygen of the ester and the imine nitrogen are both coordinated to the Ru metal to give an octahedral structure. The catalytic activity of these ruthenium carbene complexes for olefin metathesis reactions was tested. Some of the complexes bearing electron withdrawing groups had high initiation rates. These complexes exhibited excellent performance for both ring-closing metathesis and cross metathesis.

IN-SITU GENERATION OF RUTHENIUM CATALYSTS FOR OLEFIN METATHESIS

The present invention relates to a process for preparing olefins by means of metathesis, which comprises the following steps a. provision of an olefin reaction mixture containing at least one olefin, b. addition of a ruthenium compound of the general formula [RuX2L1xL2y]z (I), where X=anionic ligand; L1=uncharged π-bonding ligand; L2=uncharged electron donor ligand; x=0, 1; y=1, 2, 3; z=1, 2, c. addition of a Lewis acid and/or an anionic, noncoordinating salt, d. reaction at temperatures in the range from 30° C. to 140° C., where no addition of an alkyne or alkynol is carried out. The invention further relates to the use of this process in metathesis reactions.

Synthesis and catalytic activity of a Grubbs-Hoveyda pre-catalyst having a trimeric resting state

A Grubbs-Hoveyda pre-catalyst having a trimeric resting state based on 2,4,6-trichloro-1,3,5-triazine was synthesized and the complex was characterized by NMR, HRMS and elemental analysis. The activity of this complex for ring-closing metathesis (RCM) was

Synthesis and catalytic study of ruthenium carbene catalyst containing a Zn-porphyrin ligand

A ruthenium carbene complex containing a Zn-porphyrin ligand has been developed. The complex was characterized by 1H NMR, IR, HRMS and elemental analysis. The catalytic activity of the ruthenium carbene complex for olefin metathesis reactions w

Synthesis, structure and catalytic study of oxygen chelated ruthenium (II) carbene complex

New oxygen chelated ruthenium carbene complex containing carbonyl oxygen and ether oxygen has been developed. The X-ray structure of the complex showed that the carbonyl oxygen of the amide and the terminal oxygen of the benzylidene ether are both coordinated to the metal to give an octahedral structure. The catalytic activities of this new complex for olefin metathesis reactions were investigated and it exhibited excellent performances for the ring-closing metathesis (RCM) of diethyl diallymalonate at 30 °C and even at 0 °C. The initiation rate of the catalyst was higher than that for the Hoveyda catalyst ((H2IMes)(Cl)2Ru = C(H)(C6H 4-2-OiPr)) and it was also active for cross metathesis (CM).

Efficient ruthenium metathesis catalysts containing carborane ligands

A first generation Hoveyda-Grubbs ruthenium complex with a closo-1,2-C 2B10H11 tag has been prepared. This new catalyst was tested in ring-closing metathesis (RCM) reactions and proved to be quite efficient. In addition, t