Spiro[cyclopropane-1,2'-indan]-1'-one

Base Information

• Chemical Name: Spiro[cyclopropane-1,2'-indan]-1'-one
• CAS No.: 22228-23-5
• Molecular Formula: C₁₁H₁₀O
• Molecular Weight: 158.2
• European Community (EC) Number: 967-773-2
• Mol file: 22228-23-5.mol

Synonyms:22228-23-5;spiro[cyclopropane-1,2'-indan]-1'-one;Spiro[cyclopropane-1,2'-inden]-1'(3'H)-one;Spiro[3H-indene-2,1'-cyclopropane]-1-one;1',3'-dihydrospiro[cyclopropane-1,2'-inden]-3'-one;Spiro[cyclopropane-1,2'-[2H]inden]-1'(3'H)-one;starbld0018381;SCHEMBL11500029;F21339;EN300-3035547;1',3'-dihydrospiro[cyclopropane-1,2'-indene]-3'-one

Chemical Property of Spiro[cyclopropane-1,2'-indan]-1'-one

Chemical Property:

• Melting Point: 54-55 °C(Solv: hexane (110-54-3))
• Boiling Point: 281.7±10.0 °C(Predicted)
• PSA: 17.07000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 2.20560
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 158.073164938
• Heavy Atom Count: 12
• Complexity: 227

Purity/Quality:

97% or 98% ^*data from raw suppliers

Spiro[cyclopropane-1,2''-indan]-1''-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC12CC3=CC=CC=C3C2=O
• Uses: Spiro[cyclopropane-1,2''-indan]-1''-one is a useful synthetic intermediate that can be irradiated in methylcyclohexane or EtOH/MeOH glasses at 77K to give (E)-2-Ethylidene-1-indanone.

Technology Process of Spiro[cyclopropane-1,2'-indan]-1'-one

There total 5 articles about Spiro[cyclopropane-1,2'-indan]-1'-one 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: 51.0%

trimethylsulfoxonium iodide (1774-47-6) + Trimethyl-(1-oxo-indan-2-ylmethyl)-ammonium; iodide (76919-83-0) → spiro(indan-1-one-2,1'-cyclopropane) (22228-23-5)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; roomtemp., 3h then 40- 50 deg C, 1h;

DOI:10.1021/jo00188a001

Reference yield:

1-benzylcyclopropanecarboxylic acid (27356-91-8) → spiro(indan-1-one-2,1'-cyclopropane) (22228-23-5)

Guidance literature:

With PPA;

Reference yield:

2-Benzylacrylic acid ethyl ester (20593-63-9) → spiro(indan-1-one-2,1'-cyclopropane) (22228-23-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Irradiation

2: aq. KOH

3: polyphosphoric acid

With potassium hydroxide; PPA;

upstream raw materials:

trimethylsulfoxonium iodide

Trimethyl-(1-oxo-indan-2-ylmethyl)-ammonium; iodide

1-benzylcyclopropanecarboxylic acid

2-Benzylacrylic acid ethyl ester

Downstream raw materials:

C₁₈H₁₅NO₄

Refernces

• 1、 Ohkata, Katsuo,Akiyama, Masaki,Wada, Kenshi,Sakaue, Shun,Toda, Yoshiko,Hanafusa, Terukiyo. "Substituent Effect in Solvolysis of Spiro-1'-yl p-Nitrobenzoate". . p. 2517 - 2520. Retrieved 2007/10/02.