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

Base Information

• Chemical Name: (1R,2S,3R)-phenylcyclopropane-2-13C-1,2,3-2H₃
• CAS No.: 91230-87-4
• Molecular Formula: C₉H₁₀
• Molecular Weight: 122.144
• Mol file: 91230-87-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (1R,2S,3R)-phenylcyclopropane-2-13C-1,2,3-2H₃ 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) → (1R,2S,3R)-phenylcyclopropane-2-13C-1,2,3-2H3 (91230-87-4)

Guidance literature:

Multi-step reaction with 11 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

9: LiAlH₄ / tetrahydrofuran

10: 97 percent / PCC / CH₂Cl₂

11: Wilkinson's catalyst / benzene

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; deuteriated sodium hydroxide; phosphorus pentachloride; water-d2; cetyldimethylbenzylammonium chloride; sodium amide; pyridinium chlorochromate; Wilkinson's catalyst; chiral copper catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; ammonia; benzene;

DOI:10.1021/ja00330a046

Reference yield:

phenylacetylene-2-13C (54522-92-8) → (1R,2S,3R)-phenylcyclopropane-2-13C-1,2,3-2H3 (91230-87-4)

Guidance literature:

Multi-step reaction with 9 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

7: LiAlH₄ / tetrahydrofuran

8: 97 percent / PCC / CH₂Cl₂

9: Wilkinson's catalyst / benzene

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; deuteriated sodium hydroxide; water-d2; cetyldimethylbenzylammonium chloride; pyridinium chlorochromate; Wilkinson's catalyst; chiral copper catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; benzene;

DOI:10.1021/ja00330a046

Reference yield:

benzaldehyde (100-52-7) → (1R,2S,3R)-phenylcyclopropane-2-13C-1,2,3-2H3 (91230-87-4)

Guidance literature:

Multi-step reaction with 13 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

11: LiAlH₄ / tetrahydrofuran

12: 97 percent / PCC / CH₂Cl₂

13: Wilkinson's catalyst / benzene

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; deuteriated sodium hydroxide; phosphorus pentachloride; water-d2; tert.-butyl lithium; cetyldimethylbenzylammonium chloride; sodium amide; pyridinium chlorochromate; Wilkinson's catalyst; chiral copper catalyst; In tetrahydrofuran; 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

Refernces