methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate

Base Information

• Chemical Name: methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate
• CAS No.: 1036637-32-7
• Molecular Formula: C₁₁H₁₁NO₄
• Molecular Weight: 221.213
• Mol file: 1036637-32-7.mol

Synonyms:methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate

Chemical Property of methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate

There total 3 articles about methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + methyl 2-nitroacetate (2483-57-0) → methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate (1036637-32-7) + C11H11NO4 (893751-16-1)

Guidance literature:

With silver hexafluoroantimonate; iodosylbenzene; sodium carbonate; C₂₅H₃₀N₂O₂; copper(l) chloride; In benzene; at 20 ℃; for 3h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2011.05.113

Reference yield: 36.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + methyl 2-nitroacetate (2483-57-0) → methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate (1036637-32-7)

Guidance literature:

With CuSbF₆; iodosylbenzene; sodium carbonate; C₂₅H₃₀N₂O₂; In o-xylene; optical yield given as %ee; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.113

Reference yield:

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + methyl 2-nitroacetate (2483-57-0) → methyl (1S,2R)-1-nitro-2-phenylcyclopropanecarboxylate (1036637-32-7) + methyl (1R,2S)-1-nitro-2-phenylcyclopropanecarboxylate (874341-58-9) + 1-nitro-2-phenyl-cyclopropanecarboxylic acid methyl ester

Guidance literature:

styrene; With silver hexafluoroantimonate; copper(l) iodide; 2,2-isopropylidenebis((S)-4-phenyl-2-oxazoline); In benzene;

methyl 2-nitroacetate; With molecular sieve; iodosylbenzene; sodium carbonate; In benzene; at 20 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1021/ja056192l

upstream raw materials:

styrene

methyl 2-nitroacetate

Downstream raw materials:

C₁₁H₁₃NO₂

methyl (1S,2R)-1-amino-2-phenylcyclopropanecarboxylate

methyl (1R,2S)-1-amino-2-phenylcyclopropanecarboxylate

1-amino-2-phenylcyclopropane

Refernces

• 1、 Moreau, Benoit,Charette, Andre B.. "Expedient synthesis of cyclopropane α-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate". . p. 18014 - 18015. Retrieved 2007/10/03.