27799-79-7

Basic information

• Product Name: 5,6-Dihydrophenanthridine
• Synonyms: Phenanthridine, 5,6-dihydro-
• CAS NO: 27799-79-7
• Molecular Formula: C₁₃H₁₁N
• Molecular Weight: 181.23
• Mol File: 27799-79-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 125 °C
• Boiling Point: 370.7±12.0 °C(Predicted)
• Appearance: /
• Density: 1.117±0.06 g/cm3(Predicted)
• PKA: 3.52±0.20(Predicted)
• CAS DataBase Reference: 5,6-Dihydrophenanthridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dihydrophenanthridine(27799-79-7)
• EPA Substance Registry System: 5,6-Dihydrophenanthridine(27799-79-7)

Safety Data

• Hazardous Substances Data: 27799-79-7(Hazardous Substances Data)

Upstream product

• 1234560-10-1 C₁₈H₂₀BrNO₂ 
• 1359768-78-7 N-allyl-2-(2-furyl)aniline 
• 1015-89-0 6(5H)-phenanthridinone 
• 14548-01-7 phenanthridine N-oxide 
• 877663-24-6 N-[4-methylphenyl]sulfonyl-5,6-dihydrophenanthridine 

Downstream Products

• 83697-67-0 N-benzoyl-(6H)phenanthridine 
• 229-87-8 phenanthridine 
• 1322074-86-1 4-[(4-methylphenyl)sulfonyl]phenanthridine 
• 1322074-87-2 4-[2-nitrophenyl]sulfonylphenanthridine 
• 1322074-83-8 N-[2-nitrophenyl]sulfonyl-5,6-dihydrophenanthridine 
• 877663-24-6 N-[4-methylphenyl]sulfonyl-5,6-dihydrophenanthridine 
• 1613244-43-1 2-(4,4-dimethoxypiperidin-1-yl)-1-(phenanthridin-5(6H)-yl)propan-1-one 
• 98642-70-7 (S)-benzyl (1-oxo-1-(phenanthridin-5(6H)-yl)propan-2-yl)carbamate 
• 5412-06-6 N-methyl phenanthridinium iodide 
• 83010-18-8 (2S,3R,4S)-3-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-4-hydroxy-2-[6-oxo-6-(6H-phenanthridin-5-yl)-hexylsulfanyl]-cyclopentanone 
• 83010-18-8 (3S,4R)-3-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-4-hydroxy-2-[6-oxo-6-(6H-phenanthridin-5-yl)-hexylsulfanyl]-cyclopentanone 
• 83009-76-1 4-(tert-Butyl-dimethyl-silanyloxy)-3-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-3-cyclohexyl-propenyl]-2-[6-oxo-6-(6H-phenanthridin-5-yl)-hexylsulfanyl]-cyclopentanone 
• 88920-02-9 5,6-dihydro-5-phenacylphenanthridine 
• 80554-75-2 1-(6H-Phenanthridin-5-yl)-6-phenyl-hexane-1,6-dione 

Relevant articles and documents

Application of phenanthridine compounds to pesticides

The invention relates to an application of phenanthridine compounds shown in general formula (1) to pesticides. Part of the compounds is used as a plant virus agent and can well inhibit the tobacco mosaic virus; when used as a bactericide, the compounds have good inhibitory activity on tomato early blight, wheat scab, potato late blight, phytophthora capsici, rape sclerotinia rot, cucumber gray mould, rice sheath blight disease, cucumber fusarium wilt, cercospora brown spot of peanut, apple ring rot, wheat sharp eyespot, corn southern leaf blight, watermelon anthracnose and rice bakanae disease; when used as an insecticide, the compounds have poisonous activity on armyworms, mosquito larvae, cotton bollworms, ostrinia nubilalis, aphids, adult mites and plutella xylostella. In the formula,when molecular nitrogen is not imine, R can represent hydrogen atoms, methyl, acetyl and benzoyl; R and R represent a hydrogen atom or an oxygen atom simultaneously; R and R can represent hydroxyl, acetoxyl, methoxyl, methyleneoxy, a fluorine atom and the hydrogen atom; R is a bromine atom or the fluorine atom; R is the hydrogen atom or vinyl. When nitrogen is imine, R doesnot represent any group; one of R and R does not represent any group, and the other can represent the hydrogen atom, methoxyl, ethyoxyl, benzyloxy and a chlorine atom; R, R, R and Rrepresent the hydrogen atom.

Synthesis of phenanthridine derivatives by microwave-mediated cyclization of o-furyl(allylamino)arenes

A novel and efficient synthesis of phenanthridines and aza analogues is reported. The key step is a microwave-mediated intramolecular Diels-Alder cyclization of o-furyl(allylamino)arenes. In the presence of a catalytic amount of acid, the DA-adduct reacts further to give the dihydrophenanthridines, which easily can be oxidized to fully aromatic compounds by air in the presence of UV light or by DDQ.

Synthesis of N -arylisoindolin-1-ones via pd-catalyzed intramolecular decarbonylative coupling of N -(2-bromobenzyl)oxanilic acid phenyl esters

Ethyl and phenyl oxanilates were readily prepared from N-(2-bromobenzyl) anilines and oxalyl chloride monoethyl and monophenyl esters, respectively. It was found that the ethyl oxanilate survived in the presence of K 2CO3 in DMA at 120°C and underwent an intramolecular direct arylation using Pd(OAc)2-dppf, furnishing the 5,6-dihydrophenanthridine derivative. In contrast, the corresponding phenyl oxanilates decomposed upon exposure to K2CO3 in DMA at 120 C and were transformed into N-arylisoindolin-1-ones via Pd(OAc) 2-dppf-catalyzed intramolecular decarbonylative coupling. Except for the 4-methoxy-substituted oxanilic acid phenyl ester, other phenyl oxanilates possessing electron-withdrawing (NO2, Cl) and weak electron-donating (Me) substituents provided the N-arylisoindolin-1-ones in 43-80% yields.