1255651-99-0

Basic information

• Product Name: (2R,2'R)-dimethyl 2,2'-((2-iodo-1,3-phenylene)bis(oxy))dipropanoate
• Synonyms: (2R,2'R)-dimethyl 2,2'-((2-iodo-1,3-phenylene)bis(oxy))dipropanoate
• CAS NO: 1255651-99-0
• Molecular Weight: 408.19
• Mol File: 1255651-99-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (2R,2'R)-dimethyl 2,2'-((2-iodo-1,3-phenylene)bis(oxy))dipropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,2'R)-dimethyl 2,2'-((2-iodo-1,3-phenylene)bis(oxy))dipropanoate(1255651-99-0)
• EPA Substance Registry System: (2R,2'R)-dimethyl 2,2'-((2-iodo-1,3-phenylene)bis(oxy))dipropanoate(1255651-99-0)

Safety Data

• Hazardous Substances Data: 1255651-99-0(Hazardous Substances Data)

Upstream product

• 27871-49-4 (S)-Methyl lactate 
• 41046-67-7 2-iodoresorcinol 
• 108-46-3 recorcinol 

Downstream Products

• 1255651-84-3 dimethyl-2,2'-((2-(diacetoxy-λ³-iodanyl)-1,3-phenylene)bis(oxy))(2R,2'R)-dipropionate 
• 1226896-33-8 (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))dipropanoic acid 
• 1226896-38-3 (2R,2'R)-2,2'-((2-iodo-1,3-phenylene)bis(oxy))bis(N-mesitylpropanamide) 
• 1226896-63-4 (2,6-bis(((R)-1-(mesitylamino)-1-oxopropan-2-yl)oxy)-phenyl)-λ³-iodanediyl diacetate 

Relevant articles and documents

Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CH2CH2] → [CF2CHF] Isosterism

Saturated, fluorinated carbocycles are emerging as important modules for contemporary drug discovery. To expand the current portfolio, the synthesis of novel trifluorinated tetralins has been achieved. Fluorinated methyleneindanes serve as convenient precursors and undergo efficient difluorinative ring expansion with in situ generated p-TolIF2 (>20 examples, up to >95 %). A range of diverse substituents are tolerated under standard catalysis conditions and this is interrogated by Hammett analysis. X-ray analysis indicates a preference for the CH?F bond to occupy a pseudo-axial orientation, consistent with stabilising σC?H→σC?F* interactions. The replacement of the symmetric [CH2?CH2] motif by [CF2?CHF] removes the conformational degeneracy intrinsic to the parent tetralin scaffold leading to a predictable half-chair. The conformational behavior of this novel structural balance has been investigated by computational analysis and is consistent with stereoelectronic theory.

Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions

Molecular structures of the most prominent chiral non-racemic hypervalent iodine(III) reagents to date have been elucidated for the first time. The formation of a chirally induced supramolecular scaffold based on a selective hydrogen-bonding arrangement provides an explanation for the consistently high asymmetric induction with these reagents. As an exploratory example, their scope as chiral catalysts was extended to the enantioselective dioxygenation of alkenes. A series of terminal styrenes are converted into the corresponding vicinal diacetoxylation products under mild conditions and provide the proof of principle for a truly intermolecular asymmetric alkene oxidation under iodine(I/III) catalysis.