benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate

Base Information

• Chemical Name: benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate
• CAS No.: 1643657-35-5
• Molecular Formula: C₂₆H₂₆O₄
• Molecular Weight: 402.49

Synonyms:

Chemical Property of benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate

Chemical Property:

Purity/Quality:

≥98% ^*data from raw suppliers

MonoacylglycerolLipaseInhibitor21 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Endocannabinoids such as 2-arachidonoyl glycerol (2-AG; ) and arachidonoyl ethanolamide (AEA; ) are biologically active lipids that are involved in a number of synaptic processes including activation of cannabinoid (CB) receptors. Fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) mediate the hydrolysis of AEA and 2-AG, respectively. Monoacylglycerol Lipase Inhibitor 21 selectively binds to MAGL (Ki = 0.4 μM) and reversibly blocks the enzyme’s activity in mouse brain with an IC50 value of 0.18 μM. Comparatively, Monoacylglycerol Lipase Inhibitor 21 is reported to inhibit FAAH activity in mouse brain with an IC50 value of 59 μM. benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate does not bind CB1 or CB2 receptors and does not inhibit the related serine hydrolases ABHD6 and ABHD12 (Kis > 10 μM). In a mouse model of multiple sclerosis, 5 mg/kg of Monoacylglycerol Lipase Inhibitor 21 has been used to ameliorate progression of the disease without producing detrimental CB1-mediated effects.[Cayman Chemical] Monoacylglycerol Lipase Inhibitor 21 is an enzyme governing the inactivation of endocannabinoid 2-arachidonoglycerol (2-AG)MAGL inhibitors display analgesic and tissue-protecting effects.

Technology Process of benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate

There total 4 articles about benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate 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: 92.0%

piperonol (495-76-1) + 6-([1,1'-biphenyl]-4-yl)hexanoic acid (5002-16-4) → benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate (1643657-35-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere; Microwave irradiation;

DOI:10.1002/anie.201407807

Reference yield:

4-Phenylbenzaldehyde (3218-36-8) → benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate (1643657-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 20 °C / Microwave irradiation; Inert atmosphere

2: hydrogen; palladium 10% on activated carbon / ethanol / 40 °C / 45004.5 Torr / Microwave irradiation; Flow reactor

3: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere; Microwave irradiation

With dmap; palladium 10% on activated carbon; hydrogen; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; 1: |Wittig Olefination;

DOI:10.1002/anie.201407807

Reference yield:

6-([1,1'-biphenyl]-4-yl)hex-5-enoic acid → benzo[d][1,3]dioxol-5-ylmethyl 6-([1,1′-biphenyl]-4-yl)-hexanoate (1643657-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; palladium 10% on activated carbon / ethanol / 40 °C / 45004.5 Torr / Microwave irradiation; Flow reactor

2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere; Microwave irradiation

With dmap; palladium 10% on activated carbon; hydrogen; dicyclohexyl-carbodiimide; In ethanol; dichloromethane;

DOI:10.1002/anie.201407807

upstream raw materials:

4-Phenylbenzaldehyde

piperonol

6-([1,1'-biphenyl]-4-yl)hexanoic acid

(4-carboxybutyl)triphenylphosphonium bromide

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