1,4-Dioxaspiro[4.5]decane-8-acetonitrile

Base Information

• Chemical Name: 1,4-Dioxaspiro[4.5]decane-8-acetonitrile
• CAS No.: 124499-37-2
• Molecular Formula: C10H15NO2
• Molecular Weight: 181.23
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID90437144
• Wikidata: Q82252527
• Mol file: 124499-37-2.mol

Synonyms:124499-37-2;1,4-Dioxaspiro[4.5]decane-8-acetonitrile;2-(1,4-dioxaspiro[4.5]decan-8-yl)acetonitrile;(1,4-Dioxa-spiro[4.5]dec-8-yl)-acetonitrile;MFCD09037894;2-{1,4-dioxaspiro[4.5]decan-8-yl}acetonitrile;SCHEMBL7475971;DTXSID90437144;BLIRGGYUBXDIHJ-UHFFFAOYSA-N;ZEA49937;AB2825;AKOS006332099;SB32150;3-CHLORO-BENZIMIDICACIDETHYLESTER;AS-44656;SY243627;8-cyanomethyl-1,4-dioxaspiro[4.5]decane;FT-0690897

Chemical Property of 1,4-Dioxaspiro[4.5]decane-8-acetonitrile

Chemical Property:

• Boiling Point: 325.829 °C at 760 mmHg
• Flash Point: 130.993 °C
• PSA: 42.25000
• Density: 1.106 g/cm³
• LogP: 1.83338
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 181.110278721
• Heavy Atom Count: 13
• Complexity: 214

Purity/Quality:

99% ^*data from raw suppliers

1,4-Dioxaspiro[4.5]decane-8-acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2(CCC1CC#N)OCCO2

Technology Process of 1,4-Dioxaspiro[4.5]decane-8-acetonitrile

There total 5 articles about 1,4-Dioxaspiro[4.5]decane-8-acetonitrile 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: 97.0%

2-<4,4-(ethylenedioxy)cyclohexylidene>acetonitrile (124499-35-0) → 1,4-dioxaspiro[4.5]dec-8-yl acetonitrile (124499-37-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 25 ℃; for 4h;

DOI:10.1002/chem.201602900

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 1,4-dioxaspiro[4.5]dec-8-yl acetonitrile (124499-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DME, 0 deg C, 1 h, 2.) DME, r.t., 3 h

2: 91 percent / H₂ / 5percent Pd/C / methanol

With hydrogen; sodium hydride; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4020(01)81224-2

Reference yield:

(1,4-dioxaspiro[4.5]dec-8-yl)methanol (23521-81-5,17159-82-9) → 1,4-dioxaspiro[4.5]dec-8-yl acetonitrile (124499-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: dimethylsulfoxide / 3 h / Heating

With triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm00058a004

upstream raw materials:

sodium cyanide

(1,4-dioxaspiro[4.5]dec-8-yl)methyl methanesulfonic acid

2-<4,4-(ethylenedioxy)cyclohexylidene>acetonitrile

(1,4-dioxaspiro[4.5]dec-8-yl)methanol

Downstream raw materials:

1,4-dioxaspiro<4.5>decane-8-ethanamine

2-(4-oxocyclohexyl)acetonitrile

4-(2-Oxo-2-phenyl-ethyl)-cyclohexanone

4-(2-Oxo-hexyl)-cyclohexanone

Refernces

• 1、 Rew, Yosup,McMinn, Dustin L.,Wang, Zhulun,He, Xiao,Hungate, Randall W.,Jaen, Juan C.,Sudom, Athena,Sun, Daqing,Tu, Hua,Ursu, Stefania,Villemure, Elisia,Walker, Nigel P.C.,Yan, Xuelei,Ye, Qiuping,Powers, Jay P.. "Discovery and optimization of piperidyl benzamide derivatives as a novel class of 11β-HSD1 inhibitors". scheme or table. p. 1797 - 1801. Retrieved 2009/12/07.
• 2、 Alonso, Francisco,Mico, Irene,Najera, Carmen,Sansano, Jose M.,Yus, Miguel,et al.. "Synthesis of 3- and 4-Substituted Cyclic α-Amino Acids Structurally Related to ACPD". . p. 10259 - 10280. Retrieved 2007/10/02.