118326-92-4

Basic information

• Product Name: (1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene
• CAS NO: 118326-92-4
• Molecular Formula: C₁₄H₁₅BrO
• Molecular Weight: 279.1723
• Mol File: 118326-92-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 362°C at 760 mmHg
• Flash Point: 141.5°C
• Density: 1.437g/cm³
• Vapor Pressure: 4.15E-05mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: (1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene(CAS DataBase Reference)
• NIST Chemistry Reference: (1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene(118326-92-4)
• EPA Substance Registry System: (1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene(118326-92-4)

Safety Data

• Hazardous Substances Data: 118326-92-4(Hazardous Substances Data)

Usage

Description

(1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene is a complex and specific chemical compound characterized by its unique molecular framework. It features an 8-membered ring fused to a 5-membered ring, along with a bromine atom and an oxirene group. As a chiral molecule, it has non-superimposable mirror images, with its stereochemistry indicated by the (1aR,1bS,5aS,9bS) prefix. The distinct structural features of this compound make it a promising candidate for further study and potential applications in various scientific and industrial fields.

Uses

Used in Organic Synthesis:
(1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene is used as a key intermediate in organic synthesis for the development of new compounds with potential applications in various industries. Its unique structure and reactivity, particularly the presence of the oxirene group, make it a valuable building block for the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene is utilized as a starting material for the design and synthesis of novel pharmaceutical agents. Its distinct structural features and chirality may contribute to the development of innovative drugs with improved efficacy and selectivity.
Used in Chemical Research:
(1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene serves as a subject of interest in chemical research, where its unique properties and reactivity are investigated. This research can lead to a better understanding of the compound's behavior and potential applications in various scientific disciplines.
Used in Material Science:
In material science, (1aR,1bS,5aS,9bS)-8-bromo-1a,1b,2,3,4,5,5a,9b-octahydrophenanthro[9,10-b]oxirene may be explored for its potential use in the development of new materials with specific properties. Its unique molecular framework and the presence of the bromine atom could contribute to the creation of materials with tailored characteristics for various applications.

Upstream product

• 118326-90-2 7-bromo-trans-1,2,3,4,4a,10a-hexahydrophenanthrene 
• 118326-91-3 (4aβ,9α,10β)-7,10-dibromo-9-hydroxy-trans-1,2,3,4,4a,9,10,10a-octahydrophenanthrene 

Relevant articles and documents

SUBSTITUENT EFFECT ON THE DIASTEREOSELECTIVITY OF THE ACID HYDROLYSIS AND TRICHLOROACETOLYSIS OF 9,10-OXIDES DERIVED FROM trans-1,2,3,4,4a,10a-HEXAHYDROPHENANTHRENE. MECHANISM OF THE EPOXIDE RING OPENING

The mechanism of the acidic ring opening reactions of 2-aryloxiranes which are simple models of arene oxides, is still under discussion.Two different mechanisms have been suggested to rationalise the product distributions of the acid hydrolysis of the two types of conformationally restricted 2-aryloxiranes (2 and 3, and 5 and 6) : it would appear to be difficult to reconcile the two rationales.In order to gain insight into the reactions of benzo-epoxides of type 5 and 6, the 6-methoxy (5c and 6c) and the 7-bromo derivatives (5a and 6a) were synthesised and their acid hydrolysis (1:1 dioxane/water) and trichloroacetolysis in benzene were studied and compared with those of the unsubstituted compounds (5b and 6b).Contrary to expectations based on the results obtained with the epoxides of type 2 and 3, the introduction of the substituent on the aromatic moiety, in particular the strong electron-donating 6-methoxy, does not modify the complete anti diastereoselectivity observed in the acid hydrolysis of the unsubstituted epoxide 6b.In the case of the epoxides 5, on the contrary, the percentage of syn adduct increases noticeably with the ability of the aromatic moiety to stabilise the benzylic carbocationic centre.As for the trichloroacetolysis reactions, significant amounts of syn adducts are observed for both the epoxides 5 and 6; the syn stereoselectivity increases for both the epoxides 5 and 6 with the ability of the aryl to stabilise a benzylic carbocationic centre.A Hammet-type linear correlation was found between the diastereoselectivity and the ?'constants for the acid hydrolysis of 5a-c and for the trichloroacetolysis reactions of 5a-c and 6a-c.The results obtained are difficult to explain on the basis of either of the mechanisms hypothesised for 2-aryloxiranes, at least as they were originally proposed.