101250-48-0

Basic information

• Product Name: 5-benzylmorpholin-3-one
• Synonyms: 5-benzylmorpholin-3-one;(S)-5-benzylMorpholin-3-one;(5S)-5-(phenylMethyl)-3-Morpholinone;(5S)-5-BenzylMorpholin-3-one;(S)-5-(Phenylmethyl)-3-morpholinone;(S)-5-(Phenylmethyl)-3-morpholinone,99%e.e.;3-Morpholinone, 5-(phenylmethyl)-, (5S)
• CAS NO: 101250-48-0
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191
• Mol File: 101250-48-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-benzylmorpholin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-benzylmorpholin-3-one(101250-48-0)
• EPA Substance Registry System: 5-benzylmorpholin-3-one(101250-48-0)

Safety Data

• Hazardous Substances Data: 101250-48-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
5-Benzylmorpholin-3-one is utilized as an intermediate in the synthesis of pharmaceuticals and agrochemicals. Its unique structure allows it to serve as a building block for the development of new drugs and pesticides, contributing to advancements in healthcare and agriculture.
Used in Chemical Industry:
As a key compound in the synthesis of various organic compounds, 5-benzylmorpholin-3-one is of interest to the chemical industry. Its versatile chemical properties enable it to be incorporated into a wide range of chemical processes, leading to the production of diverse chemical products.
Used in Medicinal Research:
5-Benzylmorpholin-3-one exhibits potential biological activities and is being studied for its medicinal properties. Its unique structure and potential interactions with biological targets make it a promising candidate for the development of new therapeutic agents.

Upstream product

• 221045-94-9 (S)-(-)-2-amino-3-phenyl-1-(tert-butyldimethylsilyloxy)propane 
• 207120-52-3 (S)-2-chloro-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide 
• 3182-95-4 L-Phenylalaninol 
• 79-04-9 chloroacetyl chloride 
• 105-39-5 chloroacetic acid ethyl ester 
• 94193-78-9 (S)-2-chloro-N-(1-hydroxy-3-phenylpropan-2-yl)acetamide 
• 2382-86-7 methyl (S)-2-(2-chloroacetamido)-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 

Downstream Products

• 1607483-19-1 C₁₆H₂₃NO₄ 
• 1607483-20-4 C₁₇H₂₅NO₄ 
• 1607483-23-7 C₁₃H₂₀NO₄P 
• 1621604-13-4 (3R,5S)-5-benzylmorpholine-3-phosphonic acid 
• 169297-81-8 (S)-5-benzyl-4-(4-methoxybenzyl)morpholin-3-one 
• 60398-43-8 ((S)-2-Amino-3-phenyl-propoxy)-acetic acid 

Relevant articles and documents

A synthesis of (S)-3-(phenylmethyl)morpholine from (S)-phenylalanol

A preparation of (S)-3-(phenylmethyl)morpholine from (S)-phenylated is described.

Discovery and Characterization of (R)-6-Neopentyl-2-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (PF-06462894), an Alkyne-Lacking Metabotropic Glutamate Receptor 5 Negative Allosteric Modulator Profiled in both Rat and Nonhuman Primates

We previously observed a cutaneous type IV immune response in nonhuman primates (NHP) with the mGlu5 negative allosteric modulator (NAM) 7. To determine if this adverse event was chemotype- or mechanism-based, we evaluated a distinct series of mGlu5 NAMs. Increasing the sp3 character of high-throughput screening hit 40 afforded a novel morpholinopyrimidone mGlu5 NAM series. Its prototype, (R)-6-neopentyl-2-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (PF-06462894, 8), possessed favorable properties and a predicted low clinical dose (2 mg twice daily). Compound 8 did not show any evidence of immune activation in a mouse drug allergy model. Additionally, plasma samples from toxicology studies confirmed that 8 did not form any reactive metabolites. However, 8 caused the identical microscopic skin lesions in NHPs found with 7, albeit with lower severity. Holistically, this work supports the hypothesis that this unique toxicity may be mechanism-based although additional work is required to confirm this and determine clinical relevance.

Diastereoselective synthesis of novel 5-substituted morpholine-3-phosphonic acids: Further exploitation of N-acyliminium intermediates

The first diastereoselective total synthesis of 5-substituted morpholine-3-phosphonic acids is reported. The principal feature of the synthesis is the introduction of a dimethyl phosphonate group into 5-substituted morpholin-3-ones. The procedure is based

Amine-promoted asymmetric (4+2) annulations for the enantioselective synthesis of tetrahydropyridines: A traceless and recoverable auxiliary strategy

Gone, without a trace: The in situ reaction of 2-(acetoxymethyl)buta-2,3- dienoate and a secondary amine produces a 2-methylene-3-oxobutanoate equivalent that can be used in asymmetric [4+2] annulations with N-tosylimines to provide tetrahydropyridines in

Organic base effects in NHC promoted O- to C-carboxyl transfer; Chemoselectivity profiles, mechanistic studies and domino catalysis

The O- to C-carboxyl transfer of oxazolyl carbonates promoted by triazolinylidenes, generated in situ with NEt3, shows a markedly different rate and chemoselectivity profile to the same reaction promoted by triazolinylidenes generated using KHM

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.

Highly enantioselective intermolecular stetter reactions of β-aryl acceptors: α-ketoester moiety as handle for activation and synthetic manipulations

The use of β,γ-unsaturated-α-ketoesters in the intermolecular Stetter reaction furnishes 1,2,5-tricarbonyl compounds in high yield and excellent enantioselectivity. The α,δ-diketoesters generated using this methodology serve as useful synthetic building b

Highly asymmetric NHC-catalyzed hydroacylation of unactivated alkenes

NHC-catalysis proto(n)type: The title reaction produces 21 different chroman-4-one-type products in good yields and excellent enantioselectivities, in each case building up a new all-carbon quaternary stereocenter (see scheme). Based on DFT calculations a

4-(1,3-Thiazol-2-yl)morpholine derivatives as inhibitors of phosphoinositide 3-kinase

4-(1,3-Thiazol-2-yl)morpholine derivatives have been identified as potent and selective inhibitors of phosphoinositide 3-kinase. The SAR data of selected examples are presented and the in vivo profiling of compound 18 is shown to demonstrate the utility of this class of compounds in xenograft models of tumor growth.

FUSED THIAZOLE DERIVATIVES AS KINASE INHIBITORS

A series of 5,6-dihydro-l,3-benzothiazol-7(4H)-one derivatives, and analogues thereof, which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, being selective inhibitors of PD kinase enzymes, are accordingly of b.enefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.