86240-42-8

Basic information

• Product Name: Phosphorodichloridic acid, cyclohexyl ester
• CAS NO: 86240-42-8
• Molecular Formula: C6H11Cl2O2P
• Molecular Weight: 217.032
• Mol File: 86240-42-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Phosphorodichloridic acid, cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphorodichloridic acid, cyclohexyl ester(86240-42-8)
• EPA Substance Registry System: Phosphorodichloridic acid, cyclohexyl ester(86240-42-8)

Safety Data

• Hazardous Substances Data: 86240-42-8(Hazardous Substances Data)

Upstream product

• 108-93-0 cyclohexanol 
• 463-71-8 thiophosgene 

Downstream Products

• 1623-22-9 cyclohexyl dihydrogen phosphate 
• 110-83-8 cyclohexene 
• 130557-93-6 4-Cyclohexyloxy-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 4-oxide 
• 113977-26-7 dimorpholino-phosphinic acid cyclohexyl ester 

Relevant articles and documents

Planar chirality from the chiral pool: Diastereoselective anionic phospho-fries rearrangements at ferrocene

Exclusively, the anionic phospho-Fries rearrangement has successfully been adopted on chiral ferrocenyl phosphates, resulting in diastereomeric enriched 1,2-P,O-phosphonates (up to 95% de), which can further be converted to an enantiomerically pure phosphane. A simple synthetic protocol for the preparation of all starting materials based on several chiral-pool alcohols, chiral (di)chlorophosphates, and the respective ferrocenyl phosphates is reported. Optimized reaction conditions for the anionic phospho-Fries rearrangement allow conversions at ambient temperature and the use of variable lithium amid bases and diamines in hexane, ensure virtually quantitative yields, and avoid side reactions. The (bi)cyclic alkyl substituents result in air- and moisture-stable compounds and furthermore allow the conversion of 1,1′-substituted derivatives to 1,1′,2,2′-functionalized ferrocenes, which is reported for the first time. Simultaneous rearrangements at diferrocenyl phosphates to phosphinates and even 2-hydroxy-1,3-bis(phosphonato) ferrocenes and their workup under ambient conditions can be performed. Single-crystal diffraction analysis allowed the determination of the absolute configuration of the planar chirality of two diastereomerically pure ferrocenes being the Rp isomers. Furthermore, strong T-shaped π-π interaction patterns between aromatic C5H3 and C5H4 cycles for three compounds are observed.

Preparation of 3-substituted cephalosporins

There is described a process for preparing an enamine of formula (IX): STR1 where R2 is a carboxylic acid protecting group and R3 is the residue of a carboxylic acid derived acyl group and where R5 and R6 are the same or different C1-4 alkyl or C7-10 aralkyl groups; or taken together with the adjacent nitrogen atom form a heterocyclic ring containing from 4 to 8 carbon atoms and optionally a further heteroatom selected from oxygen and nitrogen; by reacting a compound of formula (XII): STR2 with an amine of formula HNR5 R6, the reactant of formula (XII) being prepared by reaction of an appropriate enol derivative with a phosphorus reagent. The enamines of formula (IX) are useful in the preparation of 3-hydroxycephalosporins.