53400-00-3

Basic information

• Product Name: Benzene, 1-methoxy-4-(2-phenylcyclopropyl)-, cis-
• CAS NO: 53400-00-3
• Molecular Formula: C16H16O
• Molecular Weight: 224.302
• Mol File: 53400-00-3.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-methoxy-4-(2-phenylcyclopropyl)-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-methoxy-4-(2-phenylcyclopropyl)-, cis-(53400-00-3)
• EPA Substance Registry System: Benzene, 1-methoxy-4-(2-phenylcyclopropyl)-, cis-(53400-00-3)

Safety Data

• Hazardous Substances Data: 53400-00-3(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 123-11-5 4-methoxy-benzaldehyde 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 637-69-4 4-Methoxystyrene 
• 908094-04-2 phenyldiazomethane 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 23304-25-8 p-methoxyphenyldiazomethane 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 959-23-9 4'-methoxychalcone 
• 76973-46-1 5-(4-methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 

Downstream Products

• 65691-14-7 4‐(4‐methoxyphenyl)‐1,2‐diphenylbutane‐1,4‐dione 
• 86396-69-2 3-(4-methoxyphenyl)-5-phenyl-1,2-dioxolane 
• 34221-26-6 trans-1-(4-methoxyphenyl)-2-phenylcyclopropane 

Relevant articles and documents

Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes

Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor–acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzylic radical generated in the photoredox catalysis cycle with a ketyl radical from the NHC catalysis cycle. The transformation features metal-free reaction conditions and tolerates a diverse range of functionalities.

Modular enantioselective synthesis of cis-cyclopropanes through self-sensitized stereoselective photodecarboxylation with benzothiazolines

Chiral cis-cyclopropanes are strained rigid analogues of alkyl chains, whose study and application are limited by their difficult synthesis. A modular approach from olefin materials is enabled by the discovery of the electron donor-acceptor (EDA) interaction between 2-substituted benzothiazolines and N-hydroxyphthalimide esters. These complexes are activated by visible light without photocatalysts, and the benzothiazoline reagent plays a triple role as a photoreductant, a stereoselective hydrogen-atom donor, and a Br?nsted acid. Beyond the enantioselective synthesis of cis-cyclopropanes, these results introduce benzothiazolines as accessible and easily tunable self-sensitized photoreductants.

Gold Sulfonium Benzylide Complexes Undergo Efficient Benzylidene Transfer to Alkenes

The gold sulfonium benzylide complexes [(P1)AuCHPh(SR1R2)]+ {B[3,5-CF3C6H3]4}? [P1=P(tBu)2o-biphenyl; R1, R2=-(CH2)4- (1 a); R1=Et, R2=Ph (1 b); R1=R2=Ph (1 c)] were synthesized by reaction of the gold α-chloro benzyl complex (P1)AuCHClPh with sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate and excess sulfide. Complexes 1 undergo efficient benzylidene transfer to alkenes and DMSO under mild conditions without external activation. Kinetic analysis of the reaction of 1 c with styrene was consistent with the intermediacy of the cationic gold benzylidene complex [(P1)AuCHPh]+ (I).

Iron-catalyzed synthesis of cyclopropanes by in situ generation and decomposition of electronically diversified diazo compounds

The modular synthesis of a variety of trans 1,2-disubstituted cyclopropanes in a safe and user-friendly one-pot iron-catalyzed cyclopropanation reaction is described. Easily synthesized N-nosylhydrazones are used as diazo precursors, allowing the in situ generation of electron-rich diazo compounds under mild reaction conditions and their direct participation in the cyclopropanation reaction.

Improved zinc-catalyzed simmons-smith reaction: Access to various 1,2,3-trisubstituted cyclopropanes

The Simmons-Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.

Intermolecular metal-free cyclopropanation of alkenes using tosylhydrazones

We describe the first general method for the metal-free cyclopropanation of alkenes by using N-tosylhydrazones as an in situ source of diazo compounds. This new method works with a wide variety of alkenes (styrene derivatives, dienes, enynes, and electron-deficient alkenes) by using N-tosylhydrazones derived from various ketones or aldehydes (aromatic, aliphatic, enones). The reaction is performed with the use of K2CO3 as a base to form the diazo species and is compatible with a wide array of functional groups. A new procedure for the synthesis of cyclopropanes by the formal cyclopropanation of carbonyl compounds and alkenes is described. This metal-free reaction proceeds through the base-promoted decomposition of tosylhydrazones. There is significant tolerance of the functional groups, enabling cyclopropanation in the presence of functionalities often not compatible with other methodologies.

Olefin cyclopropanation with aryl diazocompounds upon catalysis by a dirhodium(II) complex

A dirhodium(II) complex with N-perfluorooctylsulfonylprolinate ligands is found to catalyze the cyclopropanation of olefins with simple aryl diazomethanes. In contrast to previously reported dirhodium(II) catalysts, the present complex works well not only with very electron-rich olefins such as enol ethers, but also with styrenes. Consequently, the present catalyst allows to prepare functionalized diarylcyclopropanes in moderate yields with good diastereoselectivity for the cis product, whereas the enantioselectivity of the reaction appears negligible.

Gold-catalyzed annulation/fragmentation: Formation of free gold carbenes by retro-cyclopropanation

The gold(I)-catalyzed cyclization of 1-(prop-2-yn-1-yl)-2-alkenylbenzenes substituted at the benzylic position with OR groups gives 1,3-disubstituted naphthalenes with concomitant fragmentation of the alkene. One of these annulations proceeds by a retro-cyclopropanation that leads to free gold(I) carbenes.