20879-06-5

Basic information

• Product Name: 2H-1-Benzopyran, 3,4-dihydro-3-phenyl-, (S)-
• CAS NO: 20879-06-5
• Molecular Formula: C15H14O
• Molecular Weight: 210.276
• Mol File: 20879-06-5.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran, 3,4-dihydro-3-phenyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran, 3,4-dihydro-3-phenyl-, (S)-(20879-06-5)
• EPA Substance Registry System: 2H-1-Benzopyran, 3,4-dihydro-3-phenyl-, (S)-(20879-06-5)

Safety Data

• Hazardous Substances Data: 20879-06-5(Hazardous Substances Data)

Upstream product

• 1029608-17-0 C₁₆H₁₆O₂ 
• 254-04-6 2H-chromene 
• 98-80-6 phenylboronic acid 
• 6054-00-8 3-phenyl-2H-benzopyran 
• 70-11-1 α-bromoacetophenone 
• 109790-41-2 [2-(2-oxo-2-phenylethoxy)benzyl]triphenylphosphonium bromide 
• 109790-47-8 2-(o-hydroxymethylphenoxy)-1-phenylethanone 
• 90-01-7 salicylic alcohol 
• 37434-59-6 dimethyl 2-phenylmalonate 
• 591-50-4 iodobenzene 
• 90-02-8 salicylaldehyde 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 5330-38-1 4-chloro-2-hydroxymethylphenol 
• 73406-54-9 (2-Methoxymethoxyphenyl)methyl-methansulfonat 

Relevant articles and documents

Skeletal editing through direct nitrogen deletion of secondary amines

Synthetic chemistry aims to build up molecular complexity from simple feedstocks1. However, the ability to exert precise changes that manipulate the connectivity of the molecular skeleton itself remains limited, despite possessing substantial potential to expand the accessible chemical space2,3. Here we report a reaction that ‘deletes’ nitrogen from organic molecules. We show that N-pivaloyloxy-N-alkoxyamides, a subclass of anomeric amides, promote the intermolecular activation of secondary aliphatic amines to yield intramolecular carbon–carbon coupling products. Mechanistic experiments indicate that the reactions proceed via isodiazene intermediates that extrude the nitrogen atom as dinitrogen, producing short-lived diradicals that rapidly couple to form the new carbon–carbon bond. The reaction shows broad functional-group tolerance, which enables the translation of routine amine synthesis protocols into a strategy for carbon–carbon bond constructions and ring syntheses. This is highlighted by the use of this reaction in the syntheses and skeletal editing of bioactive compounds.

Iridium-Catalyzed Enantioselective Hydrogenation of Indole and Benzofuran Derivatives

Enantioselective hydrogenation of a broad spectrum of N-, O-, and S-containing aromatic benzoheterocycles or nonaromatic unsaturated heterocycles has been realized by using an Ir/SpinPHOX (SpinPHOX=spiro[4,4]-1,6-nonadiene-based phosphine-oxazoline) complex as the catalyst, affording an array of the corresponding chiral benzoheterocycles (30 examples) with excellent enantioselectivities (>99 % ee in most cases) and turnover numbers up to 500.

Iridium-Catalyzed Asymmetric Hydrogenation of 2H-Chromenes: A Highly Enantioselective Approach to Isoflavan Derivatives

A highly efficient (aS)-Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation of substituted 2H-chromenes and substituted benzo[e][1,2]oxathiine 2,2-dioxides is described. A series of 2H-chromenes and benzo[e][1,2]oxathiine 2,2-dioxides were hydrogenated to give the target products in high yields (92-99%) with excellent enantioselectivities (up to 99.7% ee) using our catalytic system. This reaction provides a direct and efficient method for the construction of chiral benzo six-membered oxygen-containing compounds.