123536-66-3

Basic information

• Product Name: (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one
• Synonyms: (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one
• CAS NO: 123536-66-3
• Molecular Weight: 252.052
• Mol File: 123536-66-3.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one(123536-66-3)
• EPA Substance Registry System: (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one(123536-66-3)

Safety Data

• Hazardous Substances Data: 123536-66-3(Hazardous Substances Data)

Usage

Description

(1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one is a bicyclic organic compound with the molecular formula C8H11IO2. It features a six-membered ring and an oxygen atom, along with an iodine atom and a ketone functional group. These characteristics make it a valuable building block for pharmaceutical and medicinal chemistry applications.

Uses

Used in Pharmaceutical and Medicinal Chemistry:
(1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one is used as an intermediate in organic synthesis for the production of various drugs and complex organic molecules. Its unique structural features and reactivity make it an important tool for chemists in the development of new chemical entities or in the modification of existing compounds for improved biological activity.

Upstream product

• 102096-64-0 (S)-Cyclohex-3-enecarboxylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 5709-98-8 (R)-cyclohex-3-enecarboxylic acid 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 67976-82-3 (1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt 
• 116733-45-0 3-<(1R)-3-Cyclohexen-1-ylcarbonyl>-1,3-oxazolidin-2-one 
• 6493-77-2 (S)-(-)-methyl 3-cyclohexene-1-carboxylate 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 5708-19-0 (1S)-3-cyclohexenecarboxylic acid 

Downstream Products

• 365997-31-5 (1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid ethyl ester 
• 365997-33-7 ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate 
• 365997-36-0 (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylic acid ethyl ester 
• 1255529-35-1 ethyl (1S,3R,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 
• 365997-34-8 ethyl (1S,3R,4S)-4-azido-3-(tert-butoxycarbonylamino)-cyclohexane-1-carboxylate 
• 365998-33-0 ethyl (1S,3R,4S)-4-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylate 
• 1255529-37-3 (1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester 
• 1255529-53-3 (1S,2R,4R)-2-[(tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester 
• 480449-84-1 ethyl (1S,3R,4S)-4-amino-3-[(tert-butoxycarbonyl)amino]-cyclohexanecarboxylate 
• 1255529-36-2 ethyl (1R,3R,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 
• 4350-83-8 (R,S)-6-oxabicyclo[3.2.1]octan-7-one 
• 912273-65-5 N₁-(5-chloropyridin-2-yl)-N₂-{(1R,2R,4S)-4-(dimethylaminocarbonyl)-2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carboxamido]cyclohexyl}oxalamide p-toluenesulfonic acid 

Relevant articles and documents

Design, synthesis, and biological activity evaluation of a series of pleuromutilin derivatives with novel C14 side chains

In this work, according to the ‘me-too me-better’ design strategy, a peculiar side chain different from lefamulin at C14 position of pleuromutilin was introduced. A series of novel thioether pleuromutilin derivatives containing cyclohexane in the C14 chain was synthesized by ten-step synthesis reaction. All derivatives were characterized by Nuclear Magnetic Resonance (NMR) and High Resolution Mass Spectrometer (HRMS). Furthermore, majority of derivatives displayed moderate antibacterial activity in vitro. However, the compound 2C and 2J exhibited comparable or superior antibacterial activity to lefamulin. The summarized structure-activity relationship not only made the variety of pleuromutilin derivatives more diverse, but also provided new ideas for its design and development.

Discovery of an Oxycyclohexyl Acid Lysophosphatidic Acid Receptor 1 (LPA1) Antagonist BMS-986278 for the Treatment of Pulmonary Fibrotic Diseases

The oxycyclohexyl acid BMS-986278 (33) is a potent lysophosphatidic acid receptor 1 (LPA1) antagonist, with a human LPA1 Kb of 6.9 nM. The structure-activity relationship (SAR) studies starting from the LPA1 antagonist clinical compound BMS-986020 (1), which culminated in the discovery of 33, are discussed. The detailed in vitro and in vivo preclinical pharmacology profiles of 33, as well as its pharmacokinetics/metabolism profile, are described. On the basis of its in vivo efficacy in rodent chronic lung fibrosis models and excellent overall ADME (absorption, distribution, metabolism, excretion) properties in multiple preclinical species, 33 was advanced into clinical trials, including an ongoing Phase 2 clinical trial in patients with lung fibrosis (NCT04308681).

Method for preparing oxabicyclooctane compound

The invention relates to a method for preparing oxabicyclooctane compound, and the method comprises following steps: mixing 3-cyclohexene-1-formic acid shown in a formula (1), iodic acid and/or iodatewhich are shown in a formula (2), and iodide and acid (expect 3-cyclohexene-1-formic acid) which are shown in a formula (3) to obtain mixed liquor; and generating oxabicyclooctane compound shown in aformula (4) in the obtained mixed liquor; wherein the iodic acid can double as acid. (In the formula (2), A1 represents hydrogen atom or alkali metal.) (In the formula (3), A3 represents alkali metal.)