1226896-33-8

Basic information

• Product Name: (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))dipropanoic acid
• Synonyms: (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))dipropanoic acid
• CAS NO: 1226896-33-8
• Molecular Weight: 380.136
• Mol File: 1226896-33-8.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))dipropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))dipropanoic acid(1226896-33-8)
• EPA Substance Registry System: (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))dipropanoic acid(1226896-33-8)

Safety Data

• Hazardous Substances Data: 1226896-33-8(Hazardous Substances Data)

Upstream product

• 1226896-32-7 (2R,2'R)-diethyl 2,2'-(2-iodo-1,3-phenylene)bis(oxy)dipropanoate 
• 108-46-3 recorcinol 
• 41046-67-7 2-iodoresorcinol 
• 1255651-99-0 (2R,2'R)-dimethyl 2,2'-((2-iodo-1,3-phenylene)bis(oxy))dipropanoate 
• 1255651-84-3 dimethyl-2,2'-((2-(diacetoxy-λ³-iodanyl)-1,3-phenylene)bis(oxy))(2R,2'R)-dipropionate 

Downstream Products

• 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 
• 1226896-40-7 (2R,2'R)-2,2'-(2-iodo-1,3-phenylene)bis(oxy)bis(N,N-diphenylpropanamide) 
• 1226896-35-0 (2R,2'R)-2,2'-((2-iodo-1,3-phenylene)bis(oxy))bis(N-phenylpropanamide) 
• 1611494-91-7 (2R,2'R)-2,2'-((2-iodo-1,3-phenylene)bis(oxy))bis(1-(piperidin-1-yl)propan-1-one) 

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.

Hypervalent Iodine(III)-Catalysed Enantioselective α-Acetoxylation of Ketones

An enantioselective catalytic synthesis of α-acetoxylated ketones through I(I)/I(III) catalysis using a resorcinol/lactamide-based chiral iodoarene is reported. Catalyst turnover by in situ generation of the active iodine(III) derivative is achieved by oxidation with mCPBA in the presence of acetic acid. The prior transformation of ketones to easily accessible acetyl enol ethers is beneficial and yields up to 97 percent with enantioselectivities up to 88 percent ee are obtained using only low catalyst loadings of only 5 mol percent under mild reaction conditions.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.