(1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

Base Information

• Chemical Name: (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride
• CAS No.: 244622-23-9
• Molecular Formula: C8H9 Cl O
• Molecular Weight: 156.612
• DSSTox Substance ID: DTXSID90449126
• Nikkaji Number: J1.156.939K
• Wikidata: Q82268485
• Mol file: 244622-23-9.mol

Synonyms:244622-23-9;DTXSID90449126;(1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride;(1S,2S,4S)-Norborna-5-ene-2-carbonyl chloride

Chemical Property of (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

Chemical Property:

• PSA: 17.07000
• LogP: 1.96400
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 156.0341926
• Heavy Atom Count: 10
• Complexity: 197

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC(C1C=C2)C(=O)Cl
• Isomeric SMILES: C1[C@H]2C[C@@H]([C@@H]1C=C2)C(=O)Cl

Technology Process of (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

There total 2 articles about (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride 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:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) → (-)-(1S,2S)-5-norbornene-2-carboxylic acid chloride (244622-23-9,214920-46-4,783334-78-1)

Guidance literature:

With phosphorus pentachloride; In diethyl ether; for 1h; Ambient temperature;

DOI:10.1016/0040-4020(96)00155-X

Reference yield:

(R)-pantolactone (1S,2S,4S)-bicyclo<2.2.1>hept-5-ene-2-carboxylate (102096-61-7) → (-)-(1S,2S)-5-norbornene-2-carboxylic acid chloride (244622-23-9,214920-46-4,783334-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol; tetrahydrofuran / 4 h / Ambient temperature

2: oxalyl chloride, DMF / CH₂Cl₂ / 2.5 h / Ambient temperature

With sodium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm970013w

Reference yield:

(-)-(1S,2S)-5-norbornene-2-carboxylic acid chloride (244622-23-9,214920-46-4,783334-78-1) → C25H27BrN4O4

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine, DMAP / 2 h / Ambient temperature

2: 2N aq. NaOH / dioxane / 4 h / Heating

3: 66 percent / magnesium monoperoxyphthalate / propan-2-ol; H₂O / 20 h / Ambient temperature

4: 83.5 percent / 6N aq. HCl / ethanol / 30 h / Ambient temperature

5: 86.8 percent / DMAP, pyridine / 20 h / 50 °C

With pyridine; hydrogenchloride; dmap; sodium hydroxide; magnesium monoperoxyphthalate hexahydrate; In 1,4-dioxane; ethanol; water; isopropyl alcohol;

DOI:10.1021/jm970013w

upstream raw materials:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(R)-pantolactone (1S,2S,4S)-bicyclo<2.2.1>hept-5-ene-2-carboxylate

Downstream raw materials:

6-amino-1,3-dipropyl-5-{[(1S,2S)-5-norbornen-2-yl-carbonyl]-(o-nitrobenzyl)}aminouracil

1,3-dipropyl-8-[5,6-exo-epoxy-(1S,2S)-norbornan-2-yl]xanthine

1,3-dipropyl-7-o-nitrobenzyl-8-[(1S,2S)-5-norbornen-2-yl]xanthine

1,3-dipropyl-7-o-nitrobenzyl-8-[5,6-exo-epoxy-(1S,2S)-norbornan-2-yl]xanthine