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1125-99-1

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1125-99-1 Usage

Chemical Properties

clear light yellow liquid

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 16, p. 1466, 1968 DOI: 10.1248/cpb.16.1466

Check Digit Verification of cas no

The CAS Registry Mumber 1125-99-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,2 and 5 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1125-99:
(6*1)+(5*1)+(4*2)+(3*5)+(2*9)+(1*9)=61
61 % 10 = 1
So 1125-99-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H17N/c1-2-6-10(7-3-1)11-8-4-5-9-11/h6H,1-5,7-9H2/p+1

1125-99-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B25622)  1-(1-Cyclohexen-1-yl)pyrrolidine, 97%   

  • 1125-99-1

  • 5g

  • 261.0CNY

  • Detail
  • Alfa Aesar

  • (B25622)  1-(1-Cyclohexen-1-yl)pyrrolidine, 97%   

  • 1125-99-1

  • 25g

  • 382.0CNY

  • Detail
  • Alfa Aesar

  • (B25622)  1-(1-Cyclohexen-1-yl)pyrrolidine, 97%   

  • 1125-99-1

  • 100g

  • 1216.0CNY

  • Detail
  • Aldrich

  • (P74001)  1-Pyrrolidino-1-cyclohexene  97%

  • 1125-99-1

  • P74001-25G

  • 276.12CNY

  • Detail

1125-99-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Pyrrolidino-1-cyclohexene

1.2 Other means of identification

Product number -
Other names 1-(cyclohexen-1-yl)pyrrolidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1125-99-1 SDS

1125-99-1Relevant articles and documents

Enamine Organocatalysts for the Thiol-Michael Addition Reaction and Cross-Linking Polymerizations

Sinha, Jasmine,Soars, Shafer,Bowman, Christopher N.

, p. 1693 - 1701 (2021)

This article describes an efficient enamine organocatalyzed thiol-Michael click reaction and its broad application in cross-linking polymerizations. A series of enamines was shown to catalyze the thiol-Michael reaction via a nucleophilic pathway. By varying the amines as well as the ring size of the ketones, enamines were designed with broad ranges of nucleophilic character ranging from 11 to 17 on the Mayr nucleophilicity scale. Upon evaluating the enamines' organocatalytic effect on the kinetics of reactions involving a thiol and Michael acceptor, wherein butyl 3-mercaptopropionate and 1-hexyl acrylate were used as model reactants, enamines were shown to outperform their base analogs. The efficiency and overall reaction yields, ranging from 11 to 92% based on the thiol conversion, were highly dependent upon the nucleophilicity of the enamines employed. Interestingly, in situ formation of an enamine via photo-deprotection of an amine in the presence of cyclic ketones facilitated the thiol-Michael reaction efficiently while simultaneously enabling higher functional group conversion. This efficiency in the reaction kinetics and conversion was extended to multifunctional derivatives, which resulted in the formation of highly cross-linked polymers.

Microwave-Assisted Facile Synthesis of Imines and Enamines using Envirocat EPZGR as a Catalyst

Varma, Rajender S.,Dahiya, Rajender

, p. 1245 - 1246 (1997)

In a simple microwave-assisted and environmentally benign approach, aldehydes and ketones react readily with primary and secondary amines to afford imines and enamines, respectively, under solvent-free conditions using Envirocat EPZGR as a catalyst.

1 microwave-induced montmorillonite-mediated facile synthesis of enamines

Yadav, Ram Naresh,Banik, Indrani,Srivastava, Ashok Kumar,Ramos, Katherine,Banik, Bimal Krishna

, p. 249 - 254 (2020)

Montmorillonite clay-mediated simple and high yielding protocol for the synthesis of various enamines with secondary amines and ketones is developed under microwave condition. This protocol is very convenient to accesses the enamines from cyclic amines with various carbonyl compounds in high yield under mild reaction conditions with short reaction time.

Synthesis and biological evaluation of asymmetrical diarylpentanoids as antiinflammatory, anti-α-glucosidase, and antioxidant agents

Leong, Sze Wei,Awin, Tahani,Mohd Faudzi, Siti Munirah,Maulidiani,Shaari, Khozirah,Abas, Faridah

, p. 2002 - 2009 (2019)

A series of seven new (1, 3, 6, 7, 10, 12, and 13) and six (2, 4, 5, 8, 9, and 11) known diarylpentanoid analogs were synthesized and assessed for their nitric oxide (NO) and α-glucosidase inhibitory activities as well as their antioxidant capacity. Nine compounds (2, 3, 4, 5, 6, 8, 11, 12, and 13) were found to exhibit comparable activity to that of curcumin (IC50= 13.0 μM), in which compound 8 has displayed strongest NO inhibitory activity with the IC50 values of 17.5 μM. Meanwhile, four compounds (1, 7, 12, and 13) were found to possess better α-glucosidase inhibitory activity than that of curcumin (30.9 μM), with the IC50 values ranging from 19.4 to 24.9 μM. On the other hand, none of the synthesized compounds has achieved better DPPH scavenging activities than that of curcumin, indicating the relatively poor antioxidant potential of desired diarylpentanoid structure. Structure-activity relationship (SAR) study disclosed that the existence of meta-hydroxyphenyl and bromo groups is crucial for antiinflammatory and anti-α-glucosidase activities, respectively. Molecular docking study showed that bromo moiety could form additional hydrophobic contacts with α-glucosidase, thereby increased the inhibition of diarylpentanoid against α-glucosidase. The overall results suggested that diarylpentanoids with poly-meta-hydroxylated phenyl ring and multiple bromo groups may lead to the discovery of new diarylpentanoids with both antiinflammatory and anti-α-glucosidase activities.

Are oxazolidinones really unproductive, parasitic species in proline catalysis? - Thoughts and experiments pointing to an alternative view

Seebach, Dieter,Beck, Albert K.,Badine, D. Michael,Limbach, Michael,Eschenmoser, Albert,Treasurywala, Adi M.,Hobi, Reinhard,Prikoszovich, Walter,Linder, Bernard

, p. 425 - 471 (2007)

The N,O-acetal and N,O-ketal derivatives (oxazolidinones) formed from proline, and aldehydes or ketones are well-known today, and they are detectable in reaction mixtures involving proline catalysis, where they have been considered 'parasitic dead ends'. We disclose results of experiments performed in the early 1970's, and we describe more recent findings about the isolation, characterization, and reactions of the oxazolidinone derived from proline and cyclohexanone. This oxazolidinone reacts (THF, room temperature) with the electrophiles β-nitrostyrene and chloral (=trichloroacetaldehyde), to give the Michael and aldol adduct, respectively, after aqueous workup (Scheme 5). The reactions occur even at -75° when catalyzed with bases such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or EtN(i-Pr)2 (DIPEA) (10%; Table 1). It is shown by NMR (Figs. 1 and 3) and IR analysis (Figs. 2 and 4) that the primarily detectable product (before hydrolysis) of the reaction with the nitro-olefin is again an oxazolidinone. When dissolved in hydroxylic solvents such as MeOH, 'hexafluoroisopropanol' ((CF3) 2CHOH; HFIP), AcOH, CF3COOH, or in LiBr-saturated THF, the ring of the oxazolidinone from cyclohexanone and proline opens up to the corresponding iminium ion (Tables 2-4), and when treated with strong bases such as DBU (in (D8)THF) the enamino-carboxylate derived from proline and cyclohexanone is formed (Scheme 8). Thus, the two hitherto putative participants (iminium ion and enamine) of the catalytic cycle (Scheme 9) have been characterized for the first time. The commonly accepted mechanism of the stereoselective C,C- or C,X-bond-forming step (i.e., A-D) of this cycle is discussed and challenged by thoughts about an alternative model with a pivotal role of oxazolidinones in the regio- and diastereoselective formation of the intermediate enamino acid (by elimination) and in the subsequent reaction with an electrophile (by trans-addition with lactonization; Schemes 11-14). The stereochemical bias between endo- and exo-space of the bicyclo[3.3.0]octane-type oxazolidinone structure (Figs. 5 and 6) is considered to possibly be decisive for the stereochemical course of events. Finally, the remarkable consistency, with which the diastereotopic Re-face of the double bond of pyrrolidino-enamines (derived from proline) is attacked by electrophiles (Schemes 1 and 15), and the likewise consistent reversal to the Si-face with bulky (Aryl) 2C-substituents on the pyrrolidine ring (Scheme 16) are discussed by invoking stereoelectronic assistance from the lone pair of pyramidalized enamine N-atoms.

Formation of aromatic rings through enamine annulation

Wang, Chen,Kohn, Harold

, p. 1773 - 1775 (2000)

(matrix presented) Condensation of pyrrolidine enamine of ketones with 1,4-diacetoxy-2-butanone provides a new, concise synthetic route to substituted benzenes, dihydroindenes, tetrahydronaphthalenes, and di- and octahydrophenanthrenes. The reaction produced modest yields with regiocontrol of the secondary amine substituent.

2-Benzoyl-6-benzylidenecyclohexanone analogs as potent dual inhibitors of acetylcholinesterase and butyrylcholinesterase

Leong, Sze Wei,Abas, Faridah,Lam, Kok Wai,Shaari, Khozirah,Lajis, Nordin H.

, p. 3742 - 3751 (2016)

In the present study, a series of 2-benzoyl-6-benzylidenecyclohexanone analogs have been synthesized and evaluated for their anti-cholinesterase activity. Among the forty-one analogs, four compounds (38, 39, 40 and 41) have been identified as lead compounds due to their highest inhibition on both AChE and BChE activities. Compounds 39 and 40 in particular exhibited highest inhibition on both AChE and BChE with IC50values of 1.6?μM and 0.6?μM, respectively. Further structure–activity relationship study suggested that presence of a long-chain heterocyclic in one of the rings played a critical role in the dual enzymes’ inhibition. The Lineweaver–Burk plots and docking results suggest that both compounds could simultaneously bind to the PAS and CAS regions of the enzyme. ADMET analysis further confirmed the therapeutic potential of both compounds based upon their high BBB-penetrating. Thus, 2-benzoyl-6-benzylidenecyclohexanone containing long-chain heterocyclic amine analogs represent a new class of cholinesterase inhibitor, which deserve further investigation for their development into therapeutic agents for cognitive diseases such as Alzheimer.

Clay catalyzed synthesis of imines and enamines under solvent-free conditions using microwave irradiation

Varma, Rajender S.,Dahiya, Rajender,Kumar, Sudhir

, p. 2039 - 2042 (1997)

The reactions of primary and secondary amines with aldehydes and ketones, respectively, are accelerated by microwaves under solvent-free conditions in the presence of montmorillonite K 10 clay to afford a high yield synthesis of imines and enamines.

Suppression of PGE2 production via disruption of MAPK phosphorylation by unsymmetrical dicarbonyl curcumin derivatives

Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Haque, Md. Areeful,Yamin, Bohari M.,Ahmad, Waqas,Amjad, Muhammad Wahab,Leong, Sze Wei,Fahmizar, Nurul Amira,Jalil, Juriyati,Abas, Faridah,Ismail, Nor Hadiani,Jantan, Ibrahim,Lam, Kok Wai

, p. 3323 - 3335 (2017)

Curcumin is an important molecule found in turmeric plants and has been reported to exhibit some profound anti-inflammatory activities by interacting with several important molecular targets found in the mitogen-activated protein kinase and NF-κβ pathways. As part of our continuing effort to search for new anti-inflammatory agents with better in vitro and in vivo efficacies, we have synthesized a series of new unsymmetrical dicarbonyl curcumin derivatives and tested their effects on prostaglandin E2 secretion level in interferon-γ/lipopolysaccharide-activated macrophage cells. Among those, five compounds exhibited remarkable suppression on prostaglandin E2 production with IC50 values ranging from 0.87 to 18.41 μM. The most potent compound 17f was found to down-regulate the expression of cyclooxygenase-2 mRNA suggesting that this series of compounds could possibly target the mitogen-activated protein kinase signal transduction pathway. Whilst the compound did not affect the expression of the conventional mitogen-activated protein kinases, the results suggest that it could disrupt the phosphorylation and activation of the proteins particularly the c-Jun N-terminal kinases. Finally, the binding interactions were examined using the molecular docking and dynamics simulation approaches.

Neurotropic activity and safety of methylene-cycloalkylacetate (MCA) derivative 3-(3-allyl-2-methylenecyclohexyl) propanoic acid

Lahiani, Adi,Haham-Geula, Dikla,Lankri, David,Cornell-Kennon, Susan,Schaefer, Erik M.,Tsvelikhovsky, Dmitry,Lazarovici, Philip

, p. 2577 - 2589 (2020)

Polyneuropathy is a disease involving multiple peripheral nerves injuries. Axon regrowth remains the major prerequisite for plasticity, regeneration, circuit formation, and eventually functional recovery and therefore, regulation of neurite outgrowth might be a candidate for treating polyneuropathies. In a recent study, we synthesized and established the methylene-cycloalkylacetate (MCAs) pharmacophore as a lead for the development of a neurotropic drug (inducing neurite/axonal outgrowth) using the PC12 neuronal model. In the present study we extended the characterizations of the in vitro neurotropic effect of the derivative 3-(3-allyl-2-methylenecyclohexyl) propanoic acid (MCA-13) on dorsal root ganglia and spinal cord neuronal cultures and analyzed its safety properties using blood biochemistry and cell counting, acute toxicity evaluation in mice and different in vitro “off-target” pharmacological evaluations. This MCA derivative deserves further preclinical mechanistic pharmacological characterizations including therapeutic efficacy in in vivo animal models of polyneuropathies, toward development of a clinically relevant neurotropic drug.

Cascade Pd(ii)-catalyzed Wacker lactonization-Heck reaction: Rapid assembly of spiranoid lactones

Albarghouti, Ghassan,Kotikalapudi, Ramesh,Lankri, David,Valerio, Viviana,Tsvelikhovsky, Dmitry

, p. 3095 - 3098 (2016)

An unprecedented Pd-catalyzed cascade Wacker-Heck lactonization-cyclization sequence is reported. The process provides a facile approach to bi- and tricyclic spiranoid lactones in good yields. The reaction shows general substrate scope and a broad functional group tolerability. In addition, a rare 4-exo trig Heck-type cyclization is demonstrated.

Synthesis of small molecules targeting paclitaxel-induced MyD88 expression in triple-negative breast cancer cell lines

Poh Yen, Khor,Stanslas, Johnson,Zhang, Tianshu,Li, Hongyuan,Wang, Xiaohui,Kok Meng, Chan,Kok Wai, Lam

, (2021/10/04)

Acquired paclitaxel (PTX) chemoresistance in triple-negative breast cancer (TNBC) can be inferred from the overexpression of toll-like receptor 4 (TLR4) and myeloid differentiation primary response 88 (MyD88) proteins and the activation of the TLR4/MyD88 cascading signalling pathway. Finding a new inhibitor that can attenuate the activation of this pathway is a novel strategy for reducing PTX chemoresistance. In this study, a series of small molecule compounds were synthesised and tested in combination with PTX against TNBC cells. The trimethoxy-substituted compound significantly decreased MyD88 overexpression and improved PTX activity in MDA-MB-231TLR4+ cells but not in HCCTLR4? cells. On the contrary, the trifluoromethyl-substituted compound with PTX synergistically improved the growth inhibition in both TNBC subtypes. The fluorescence titrations indicated that both compounds could bind with MD2 with good and comparable binding affinities. This was further supported by docking analysis, in which both compounds fit perfectly well and form some critical binding interactions with MD2, an essential lipid-binding accessory to TLR4 involved in activating the TLR-4/MyD88-dependent pathway.

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