1,3-Dioxoisoindolin-2-yl cyclohexanecarboxylate

Base Information

• Chemical Name: 1,3-Dioxoisoindolin-2-yl cyclohexanecarboxylate
• CAS No.: 126812-30-4
• Molecular Formula: C₁₅H₁₅NO₄
• Molecular Weight: 273.288
• European Community (EC) Number: 847-051-2
• Nikkaji Number: J3.406.977H
• Mol file: 126812-30-4.mol

Synonyms:126812-30-4;1,3-Dioxoisoindolin-2-yl cyclohexanecarboxylate;2-[(cyclohexylcarbonyl)oxy]-1H-isoindole-1,3(2H)-dione;(1,3-dioxoisoindol-2-yl) cyclohexanecarboxylate;1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl cyclohexanecarboxylate;ChemDiv3_004163;Cambridge id 7029765;SCHEMBL13479740;HMS1484N05;BFA81230;MFCD02189535;STK223456;AKOS001665480;AT20652;IDI1_022073;CS-0216935;EN300-6489204;AN-979/15447008;SR-01000504847;A1-33265;SR-01000504847-1;BRD-K17570253-001-01-0

Chemical Property of 1,3-Dioxoisoindolin-2-yl cyclohexanecarboxylate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 273.10010796
• Heavy Atom Count: 20
• Complexity: 404

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dioxoisoindolin-2-ylcyclohexanecarboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(CC1)C(=O)ON2C(=O)C3=CC=CC=C3C2=O

Technology Process of 1,3-Dioxoisoindolin-2-yl cyclohexanecarboxylate

There total 7 articles about 1,3-Dioxoisoindolin-2-yl cyclohexanecarboxylate 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: 99.0%

N-hydroxyphthalimide (524-38-9) + Cyclohexanecarboxylic acid (98-89-5) → 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate (126812-30-4)

Guidance literature:

Cyclohexanecarboxylic acid; With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; for 0.0166667h; Schlenk technique; Inert atmosphere;

N-hydroxyphthalimide; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.3390/molecules23040764

Reference yield: 99.0%

N-hydroxyphthalimide (524-38-9) + cyclohexanecarbaldehyde (2043-61-0) → 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate (126812-30-4)

Guidance literature:

With tert.-butylnitrite; In acetonitrile; at 25 ℃; for 12h; Concentration; Solvent; Catalytic behavior; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.1021/acs.orglett.1c03434

Reference yield:

bis(1,3-dioxoisoindolin-2-yloxy)manganese + cyclohexanylcarbonyl chloride (2719-27-9) → 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate (126812-30-4)

Guidance literature:

In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1002/bkcs.11461

upstream raw materials:

N-hydroxyphthalimide

Cyclohexanecarboxylic acid

cyclohexanylcarbonyl chloride

cyclohexanecarbaldehyde

Downstream raw materials:

2,3-dihydro-2-methyl-1H-inden-1-one

2-cyclohexylbenzimidazole

N-(bis(4-methoxyphenyl)methylene)cyclohexanamine

N-[bis(4-tolyl)methylene]cyclohexanamine

Refernces

• 1、 Aisha, Aertuke,Jin, Can,Li, Deyu,Sun, Bin,Zhu, Rui,Zhuang, Xiaohui. "Visible-Light-Triggered Decarboxylative Alkylation of 8-Acylaminoquinoline with N -Hydroxyphthalimide Ester". . p. 677 - 682. Retrieved 2020.
• 2、 Chan, Chun-Ming,Xing, Qi,Chow, Yip-Chi,Hung, Sing-Fung,Yu, Wing-Yiu. "Photoredox Decarboxylative C(sp3)-N Coupling of α-Diazoacetates with Alkyl N-Hydroxyphthalimide Esters for Diversified Synthesis of Functionalized N-Alkyl Hydrazones". . p. 8037 - 8043. Retrieved 2019.
• 3、 Kyne, Sara Helen,Li, Jiacheng,Siang Tan, Suan,Wai Hong Chan, Philip. "Minisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light". supporting information. . Retrieved 2022/01/11.
• 4、 Brauer, Jan,Quraishi, Elisabeth,Kammer, Lisa Marie,Opatz, Till. "Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**". supporting information. p. 18168 - 18174. Retrieved 2021/11/30.