(1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H₃ acid

Base Information

• Chemical Name: (1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H₃ acid
• CAS No.: 91230-93-2
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 166.153
• Mol file: 91230-93-2.mol

Synonyms:(1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H₃ acid

Chemical Property of (1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H₃ acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H₃ acid

There total 10 articles about (1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H₃ acid 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:

acetophenone-β-13C (71777-36-1) → (1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H3 acid (91230-93-2)

Guidance literature:

Multi-step reaction with 8 steps

1: PCl₅ / benzene / 5 h / 0 °C

2: NaNH₂ / liquid ammonia; diethyl ether / 3 h / -78 °C

3: 87 percent / D₂O, benzylhexadecyldimethylammonium chloride, NaOD / CH₂Cl₂

4: 2.) n-butyllithium / 1.) irradiation 20 min; 2.) n-butyllithium, hexane, THF, -78 deg C, 4 h 15 min

5: chiral copper catalyst / ethanol; cyclohexane / 70 °C

6: 82 percent / NaOH 25percent / methanol

8: 25percent NaOH / methanol

With sodium hydroxide; n-butyllithium; deuteriated sodium hydroxide; phosphorus pentachloride; water-d2; cetyldimethylbenzylammonium chloride; sodium amide; chiral copper catalyst; In methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; ammonia; benzene;

DOI:10.1021/ja00330a046

Reference yield:

phenylacetylene-2-13C (54522-92-8) → (1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H3 acid (91230-93-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / D₂O, benzylhexadecyldimethylammonium chloride, NaOD / CH₂Cl₂

2: 2.) n-butyllithium / 1.) irradiation 20 min; 2.) n-butyllithium, hexane, THF, -78 deg C, 4 h 15 min

3: chiral copper catalyst / ethanol; cyclohexane / 70 °C

4: 82 percent / NaOH 25percent / methanol

6: 25percent NaOH / methanol

With sodium hydroxide; n-butyllithium; deuteriated sodium hydroxide; water-d2; cetyldimethylbenzylammonium chloride; chiral copper catalyst; In methanol; ethanol; dichloromethane; cyclohexane;

DOI:10.1021/ja00330a046

Reference yield:

benzaldehyde (100-52-7) → (1S,2S,3R)-(+)-2-phenylcyclopropanecarboxylic-3-13C-1,2,3-2H3 acid (91230-93-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) tert-butyllithium / 1.) pentane, -78 deg C, 2.45 h; 2.) pentane, ether, -78 deg C, 7 h

2: PCC / CH₂Cl₂

3: PCl₅ / benzene / 5 h / 0 °C

4: NaNH₂ / liquid ammonia; diethyl ether / 3 h / -78 °C

5: 87 percent / D₂O, benzylhexadecyldimethylammonium chloride, NaOD / CH₂Cl₂

6: 2.) n-butyllithium / 1.) irradiation 20 min; 2.) n-butyllithium, hexane, THF, -78 deg C, 4 h 15 min

7: chiral copper catalyst / ethanol; cyclohexane / 70 °C

8: 82 percent / NaOH 25percent / methanol

10: 25percent NaOH / methanol

With sodium hydroxide; n-butyllithium; deuteriated sodium hydroxide; phosphorus pentachloride; water-d2; tert.-butyl lithium; cetyldimethylbenzylammonium chloride; sodium amide; pyridinium chlorochromate; chiral copper catalyst; In methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; ammonia; benzene;

DOI:10.1021/ja00330a046

upstream raw materials:

acetophenone-β-¹³C

phenylacetylene-2-13C

benzaldehyde

1-phenylethanol-2-13C

Downstream raw materials:

(1R,2S,3R)-phenylcyclopropane-2-13C-1,2,3-2H₃

(1S,2S,3R)-2-phenylcyclopropanemethanol-3-13C-1,2,3-2H₃

Refernces