Category: pyrrolines

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 58081-05-3, is researched, SMILESS is O=C1OC[C@H](O)C1, Molecular C4H6O3Journal, Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) called Chiroptical properties of lactones. II. Electronic rotatory strengths of the n .far. π* transition in saturated γ- and δ-lactones, Author is Richardson, Frederick S.; Pitts, William, the main research direction is lactone chiroptical property MO; CD lactone INDO; energy level transition lactone; ionization potential lactone MO; dipole moment lactone MO; butyrolactone chiroptical property MO; valerolactone chiroptical property MO.SDS of cas: 58081-05-3.

The chiroptical properties associated with the n→π* transition of dissymmetric saturated γ- and δ-lactones were calculated and relations between the chiroptical observables and the stereochem. and electronic structural features were examined The calculations were based on the INDO MO method for the electronic structure of the mol. systems and excited states were constructed in the virtual orbital-CI approximation The highest and second highest occupied orbitals calculated for each of the 17 structures studied are, resp., the inplane n and the out-of-plane π° nonbonding orbitals localized on the O:CO group. The lowest lying singlet state is nπ* and the calculated transition wavelengths for transitions in this state are 197-230 nm. The calculated n→π* rotatory strengths and dissymmetry factors agree with experiment

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Name: 4-Methoxypiperidine. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Methoxypiperidine, is researched, Molecular C6H13NO, CAS is 4045-24-3, about Copper-Catalyzed ortho-Selective Dearomative C-N Coupling of Simple Phenols with O-Benzoylhydroxylamines. Author is Yao, Zhi-Li; Wang, Lei; Shao, Nan-Qi; Guo, Yin-Long; Wang, Dong-Hui.

In the presence of Cu(OTf)2 and LiOt-Bu in THF, 2,6-disubstituted phenols such as 2,6-dimethylphenol underwent regioselective dearomative coupling reactions with secondary O-benzoylhydroxylamines such as 4-(benzoyloxy)morpholine to yield aminocyclohexadienones such as I. Lack of inhibition with radical trapping agents, lack of rearrangement with a cyclopropylated phenol, and mass spectrometric detection of intermediates in the reaction support a mechanism involving either a single-electron transfer process involving attack of an N-centered radical onto the phenol or a two-electron pathway involving addition of phenol to an electrophilic Cu(III)-amino complex via an inner-sphere process.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Choi, Hyukjae; Mascuch, Samantha J.; Villa, Francisco A.; Byrum, Tara; Teasdale, Margaret E.; Smith, Jennifer E.; Preskitt, Linda B.; Rowley, David C.; Gerwick, Lena; Gerwick, William H. published the article 《Honaucins A-C, Potent Inhibitors of Inflammation and Bacterial Quorum Sensing: Synthetic Derivatives and Structure-Activity Relationships》. Keywords: honaucin structure activity relationship inflammation.They researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Product Details of 58081-05-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:58081-05-3) here.

Honaucins A-C were isolated from the cyanobacterium Leptolyngbya crossbyana which was found overgrowing corals on the Hawaiian coast. Honaucin A consists of (S)-3-hydroxy-γ-butyrolactone and 4-chlorocrotonic acid, which are connected via an ester linkage. Honaucin A and its two natural analogs exhibit potent inhibition of both bioluminescence, a quorum-sensing-dependent phenotype, in Vibrio harveyi BB120 and lipopolysaccharide-stimulated nitric oxide production in the murine macrophage cell line RAW264.7. The decrease in nitric oxide production was accompanied by a decrease in the transcripts of several proinflammatory cytokines, most dramatically interleukin-1β. Synthesis of honaucin A, as well as a number of analogs, and subsequent evaluation in anti-inflammation and quorum-sensing inhibition bioassays revealed the essential structural features for activity in this chem. class and provided analogs with greater potency in both assays.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

HPLC of Formula: 4045-24-3. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Methoxypiperidine, is researched, Molecular C6H13NO, CAS is 4045-24-3, about Lanthanide-Catalyzed Tandem Addition of Amines to Cyanoalkenes: Synthesis of Cyclic Amidines.

A tandem insertion of aliphatic nitriles and unactivated alkenes RCH(CN)CH2C(R1)=C(R2)R3 (R = Ph, 2-thienyl, 3-pyridinyl, etc.; R1 = H, Me; R2 = H, Me, Ph, 2-naphthyl, etc.; R3 = H, Me) to the N-H bond of secondary aliphatic amines such as dibenzylamine, pyrrolidine, thiomorpholine, etc. catalyzed by simple trialkyl rare-earth metal complexes was disclosed. This reaction provides a highly atom-economic and stereoselective way to a range of cyclic amidines I (R4 = benzyl(methyl)aminyl, tetrahydroisoquinolin-2-yl, thiomorpholin-4-yl, etc.) under mild reaction conditions.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Copper-Catalyzed ortho-Selective Dearomative C-N Coupling of Simple Phenols with O-Benzoylhydroxylamines, published in 2019-08-02, which mentions a compound: 4045-24-3, mainly applied to aminocyclohexadienone regioselective preparation; copper catalyst regioselective dearomative coupling phenol benzoylhydroxylamine; mechanism lack radical inhibition dearomative coupling phenol benzoylhydroxylamine, Application of 4045-24-3.

In the presence of Cu(OTf)2 and LiOt-Bu in THF, 2,6-disubstituted phenols such as 2,6-dimethylphenol underwent regioselective dearomative coupling reactions with secondary O-benzoylhydroxylamines such as 4-(benzoyloxy)morpholine to yield aminocyclohexadienones such as I. Lack of inhibition with radical trapping agents, lack of rearrangement with a cyclopropylated phenol, and mass spectrometric detection of intermediates in the reaction support a mechanism involving either a single-electron transfer process involving attack of an N-centered radical onto the phenol or a two-electron pathway involving addition of phenol to an electrophilic Cu(III)-amino complex via an inner-sphere process.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Seebach, Dieter; Eberle, Martin researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Recommanded Product: (R)-4-Hydroxydihydrofuran-2(3H)-one.They published the article 《(R)-Ethyl 4-tert-butoxy-3-hydroxybutanoate, a versatile chiral building block for EPC (enantiomerically pure compound) syntheses, by yeast reduction of ethyl 4-tert-butoxy-3-oxobutanoate》 about this compound( cas:58081-05-3 ) in Synthesis. Keywords: butoxyoxobutanoate stereoselective reduction yeast; butoxyhydroxybutanoate; chiral hydroxy ester preparation. We’ll tell you more about this compound (cas:58081-05-3).

Treatment of ROCH2COCH2CO2R1 (I; R = Me3C, R1 = Et) with baker’s yeast and sucrose in H2O at 28° for 4 days gave 72% (R)-ROCH2CH(OH)CH2CO2R1 (II; R = Me3C, R1 = Et) in 97% enantiomeric excess. Similar treatment of I (R = Me3C, R1 = Me; R = PhCH2, R1 = Et) gave 70 and 58% II in 82 and 56% enantiomeric excess resp.

Although many compounds look similar to this compound(58081-05-3)Recommanded Product: (R)-4-Hydroxydihydrofuran-2(3H)-one, numerous studies have shown that this compound(SMILES:O=C1OC[C@H](O)C1), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Nonbisphosphonate inhibitors of Plasmodium falciparum FPPS/GGPPS, published in 2021-06-01, which mentions a compound: 4045-24-3, mainly applied to azepanylpropyl azaheterocyclylalkyl arylthiazolecarboxamide heteroarylcarboxamide preparation antimalarial agent; structure azaheterocyclylalkyl arylthiazolecarboxamide inhibition malarial farnesyldiphosphate geranylgeranyldiphosphate synthase; lipophilicity solubility biol permeation metabolism antimalarial activity azepanylpropyl arylthiazolecarboxamide; Farnesyl/Geranylgeranyl diphosphate synthase; Malaria; Plasmodium falciparum; SAR; Thiazole, Application In Synthesis of 4-Methoxypiperidine.

A series of novel thiazole-containing amides such as I.TFA were synthesized as inhibitors of Plasmodium falciparum farnesyldiphosphate synthase (PfFPPS) and geranylgeranyldiphosphate synthase (PfGGPPS). A structure-activity relationship study of these compounds led to the identification of potent and selective PfFPPS/GGPPS inhibitors with good in vitro ADME profiles. The most promising candidate mols. were progressed to mouse in vivo PK studies and demonstrated adequate free drug exposure to warrant further investigation.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Synthetic Route of C4H6O3. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Chiroptical properties of lactones. II. Electronic rotatory strengths of the n .far. π* transition in saturated γ- and δ-lactones. Author is Richardson, Frederick S.; Pitts, William.

The chiroptical properties associated with the n→π* transition of dissymmetric saturated γ- and δ-lactones were calculated and relations between the chiroptical observables and the stereochem. and electronic structural features were examined The calculations were based on the INDO MO method for the electronic structure of the mol. systems and excited states were constructed in the virtual orbital-CI approximation The highest and second highest occupied orbitals calculated for each of the 17 structures studied are, resp., the inplane n and the out-of-plane π° nonbonding orbitals localized on the O:CO group. The lowest lying singlet state is nπ* and the calculated transition wavelengths for transitions in this state are 197-230 nm. The calculated n→π* rotatory strengths and dissymmetry factors agree with experiment

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2,6-Dichloro-3-fluoropyridine(SMILESS: ClC1=NC(=CC=C1F)Cl,cas:52208-50-1) is researched.Synthetic Route of C4H6O3. The article 《New synthesis method of 2,6-dichloro-3-fluoropyridine》 in relation to this compound, is published in Huagong Shikan. Let’s take a look at the latest research on this compound (cas:52208-50-1).

2, 6-Dichloro-3-nitropyridine was synthesized from 2, 6-dichloropyridine by nitrification reaction. Then 2,6-dichloro-3-aminopyridine was synthesized from 2,6-dichloro-3-nitropyridine by the catalytic hydrogenation reduction reaction. At last, 2,6-dichloro-3-fluoropyridine was synthesized from 2,6-dichloro-3-aminopyridine by the diazotization reaction. Overall yield of three steps reaction was 69.3%. The target compound was confirmed by MS and NMR. The factors such as nitric acid concentration, the type and amount of catalyst and the molar ratio of sodium nitrite were discussed in detail. This synthesis route has high yield, high selectivity, and better prospect of industrialization.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Quality Control of 4-Methoxypiperidine. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Methoxypiperidine, is researched, Molecular C6H13NO, CAS is 4045-24-3, about Optimization of WZ4003 as NUAK inhibitors against human colorectal cancer. Author is Yang, Huali; Wang, Xiaobing; Wang, Cheng; Yin, Fucheng; Qu, Lailiang; Shi, Cunjian; Zhao, Jinhua; Li, Shang; Ji, Limei; Peng, Wan; Luo, Heng; Cheng, Maosheng; Kong, Lingyi.

NUAK, the member of AMPK (AMP-activated protein kinase) family of protein kinases, is phosphorylated and activated by the LKB1 (liver kinase B1) tumor suppressor protein kinase. Recent work has indicated that NUAK1 is a key component of the antioxidant stress response pathway, and the inhibition of NUAK1 will suppress the growth and survival of colorectal tumors. As a promising target for anticancer drugs, few inhibitors of NUAK were developed. With this goal in mind, based on NUAK inhibitor WZ4003, a series of derivatives has been synthesized and evaluated for anticancer activity. Compound I, a derivative of WZ4003 by removing a methoxy group, was found to be the most potential one with stronger inhibitory against NUAK1/2 enzyme activity, tumor cell proliferation and inducing apoptosis of tumor cells. By in vivo efficacy evaluations of colorectal SW480 xenografts, I suppresses tumor growth more effectively with an excellent safety profile in vivo and is therefore seen as a suitable candidate for further investigation.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem