Category: 6346-09-4

Miller, Eric J. published the artcileDiscovery of Tetrahydroisoquinoline-Containing CXCR4 Antagonists with Improved in Vitro ADMET Properties, HPLC of Formula: 6346-09-4, the publication is Journal of Medicinal Chemistry (2018), 61(3), 946-979, database is CAplus and MEDLINE.

CXCR4 is a seven-transmembrane receptor expressed by hematopoietic stem cells and progeny, as well as by ≥48 different cancers types. CXCL12, the only chemokine ligand of CXCR4, is secreted within the tumor microenvironment, providing sanctuary for CXCR4⁺ tumor cells from immune surveillance and chemotherapeutic elimination by (1) stimulating prosurvival signaling and (2) recruiting CXCR4⁺ immunosuppressive leukocytes. Addnl., distant CXCL12-rich niches attract and support CXCR4⁺ metastatic growths. Accordingly, CXCR4 antagonists can potentially obstruct CXCR4-mediated prosurvival signaling, recondition the CXCR4⁺ leukocyte infiltrate from immunosuppressive to immunoreactive, and inhibit CXCR4⁺ cancer cell metastasis. Current small mol. CXCR4 antagonists suffer from poor oral bioavailability and off-target liabilities. Herein, we report a series of novel tetrahydroisoquinoline-containing CXCR4 antagonists designed to improve intestinal absorption and off-target profiles. Structure-activity relationships regarding CXCR4 potency, intestinal permeability, metabolic stability, and cytochrome P 450 inhibition are presented.

Journal of Medicinal Chemistry published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, HPLC of Formula: 6346-09-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gazizov, Mukattis B. published the artcileSynthesis and properties of 4-(dibromomethyl)benzenecarbaldehyde, SDS of cas: 6346-09-4, the publication is Tetrahedron Letters (2016), 57(2), 210-212, database is CAplus.

The 4-(dibromomethyl)benzenecarbaldehyde was synthesized for the first time using a new method, which also allowed the co-preparation of terephthalic aldehyde. The reaction of this aldehyde with primary amines RNH₂ [R = CH(CH₃)₂, 4-OCH₃C₆H₄, CH₂CH(O(C₂H₅)₂), etc.] resulted in the formation of imines RN=CHC₆H₄CHBr₂, including those containing an addnl. acetal group, while the reaction with trialkyl orthoformates HC(OR¹)₃ (R¹ = Me, Et) led to the formation of acetals R¹O(OR¹)CHC₆H₄CHBr₂. The latter compounds were transformed into 4-(dibromomethyl)-substituted benzenes containing a phosphorus functional group in the side chain via consecutive reactions with phosphorus trichloride and the esters of P(III) acids.

Tetrahedron Letters published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, SDS of cas: 6346-09-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gazizov, M. B. published the artcile4-(Dibromomethyl)benzaldehyde and its reactions with primary amines, Synthetic Route of 6346-09-4, the publication is Russian Journal of General Chemistry (2015), 85(9), 2209-2211, database is CAplus.

The title compound, 4-Br₂CHC₆H₄CHO (1) was prepared by reaction of 1,4-(Br₂CH)₂C₆H₄ with tri-Me phosphate with 42% yield, the side product being di-Me phosphorobromidate (MeO)₂P(O)Br. The process shows advantages over usual acid hydrolysis, being selective and leaving less aggressive hydrogen bromide waste. The aldehyde 1 reacts with primary amines RNH₂, giving aldimines 4-Br₂CHC₆H₄CH:NR [13a–d; R = ⁱPr, 4-MeOC₆H₄, CH₂CH(OEt)₂, (CH₂)₃CH(OEt)₂].

Russian Journal of General Chemistry published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, Synthetic Route of 6346-09-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gazizov, M. B. published the artcileSynthesis of 4-(dibromomethyl)benzenecarbaldehyde and its reactions with N- and O-nucleophiles, Product Details of C8H19NO2, the publication is Russian Chemical Bulletin (2016), 65(1), 191-194, database is CAplus.

4-(Dibromomethyl)benzenecarbaldehyde (4-Br₂CHC₆H₄CHO, I) was prepared chemoselectively by debromination of 1,4-bis(dibromomethylbenzene) with tri-Me phosphate; reaction with primary amines RNH₂ [R = i-Pr, 4-MeOC₆H₄, (EtO)₂CHCH₂, (EtO)₂CH₂CH₂CH₂] yielded benzaldimines 4-Br₂CHC₆H₄CH:NR [R = i-Pr, 4-MeOC₆H₄, (EtO)₂CHCH₂, (EtO)₂CH₂CH₂CH₂], while reaction with tri-Me and tri-Et orthoformates in the presence of H₂SO₄ yielded the acetals 4-Br₂CHC₆H₄CH(OR¹)₂ (R¹ = Me, Et).

Russian Chemical Bulletin published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, Product Details of C8H19NO2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ma, Xiao-Yan published the artcileConcise and efficient syntheses of methyl 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine, Synthetic Route of 6346-09-4, the publication is Canadian Journal of Chemistry (2020), 98(4), 191-193, database is CAplus.

Me 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine are important biosynthetic intermediates for tropane alkaloids. A concise method to synthesize these two compounds from the key intermediate N-methylpyrrolinium cation has been developed. Me 4-(1-methylpyrrolidin-2-yl)-3-oxobutanoate and hygrine were obtained in four and six steps from com. available 4,4-diethoxybutylamine with overall yields of 42% and 25%, resp.

Canadian Journal of Chemistry published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, Synthetic Route of 6346-09-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ghislieri, Diego published the artcileEngineering an Enantioselective Amine Oxidase for the Synthesis of Pharmaceutical Building Blocks and Alkaloid Natural Products, COA of Formula: C8H19NO2, the publication is Journal of the American Chemical Society (2013), 135(29), 10863-10869, database is CAplus and MEDLINE.

The development of cost-effective and sustainable catalytic methods for the production of enantiomerically pure chiral amines is a key challenge facing the pharmaceutical and fine chem. industries. This challenge is highlighted by the estimate that 40-45% of drug candidates contain a chiral amine, fueling a demand for broadly applicable synthetic methods that deliver target structures in high yield and enantiomeric excess. Herein we describe the development and application of a “toolbox” of monoamine oxidase variants from Aspergillus niger (MAO-N) which display remarkable substrate scope and tolerance for sterically demanding motifs, including a new variant, which exhibits high activity and enantioselectivity toward substrates containing the aminodiphenylmethane (benzhydrylamine) template. By combining rational structure-guided engineering with high-throughput screening, it has been possible to expand the substrate scope of MAO-N to accommodate amine substrates containing bulky aryl substituents. These engineered MAO-N biocatalysts have been applied in deracemization reactions for the efficient asym. synthesis of the generic active pharmaceutical ingredients Solifenacin and Levocetirizine as well as the natural products (R)-coniine, (R)-eleagnine, and (R)-leptaflorine. We also report a novel MAO-N mediated asym. oxidative Pictet-Spengler approach to the synthesis of (R)-harmicine.

Journal of the American Chemical Society published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, COA of Formula: C8H19NO2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Askey, Hannah E. published the artcilePhotocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines, Quality Control of 6346-09-4, the publication is Journal of the American Chemical Society (2021), 143(39), 15936-15945, database is CAplus and MEDLINE.

A solution to these problems using organophotoredox catalysis, enabling a direct, modular and sustainable preparation of α-(di)substituted γ-arylamines, including challenging electron-neutral and moderately electron-rich aryl groups was reported. A broad range of functionalities were tolerated, and the reactions was run on multigram scale in continuous flow. The method was applied to a concise, protecting-group-free synthesis of the blockbuster drug Fingolimod, as well as a phosphonate mimic of its in-vivo active form (by iterative α-C-H functionalization of ethanolamine). The reaction was sequenced with an intramol. N-arylation to provided a general and modular access to valuable (spirocyclic) 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydronaphthyridines. Mechanistic and kinetic studies supportes an irreversible hydrogen atom transfer activation of the alkylamine by the azidyl radical and some contribution from a radical chain. The reaction was photon-limited and exhibits a zero-order dependence on amine, azide, and photocatalyst, with a first-order dependence on styrene.

Journal of the American Chemical Society published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, Quality Control of 6346-09-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Smolobochkin, A. V. published the artcileSynthesis of novel 2-arylpyrrolidines by the reaction of 1-(4,4-diethoxybutyl)urea with resorcinols, Name: 4,4-Diethoxybutan-1-amine, the publication is Russian Chemical Bulletin (2014), 63(1), 284-285, database is CAplus.

Reaction of 1-(4,4-diethoxybutyl)urea with resorcinol, 2-methylresorcinol, and pyrogallol in chloroform in the presence of trifluoroacetic acid affords new 2,2′-(1,3-phenylene)bis(pyrrolidine-1-carboxamides).

Russian Chemical Bulletin published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C24H29N5O3, Name: 4,4-Diethoxybutan-1-amine.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bogdanov, A. V. published the artcileSynthesis of New (2-Acetamido)phenylglyoxylamides Containing an Acetal Fragment, Application of 4,4-Diethoxybutan-1-amine, the publication is Russian Journal of Organic Chemistry (2019), 55(1), 121-123, database is CAplus.

Mild opening of the five-membered ring in 1-acetylisatins by the action of an equimolar amount of 4,4-diethoxybutan-1-amine afforded 2-(2-acetamidophenyl)-N-(4,4-diethoxybutyl)-2-oxoacetamides in almost quant. yield.

Russian Journal of Organic Chemistry published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, Application of 4,4-Diethoxybutan-1-amine.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Smolobochkin, A. V. published the artcileTandem intramolecular cyclisation/1,3-aryl shift in N-(4,4-diethoxybutyl)-1-arylmethanimines (Kazan reaction): synthesis of 3-benzylidene-1-pyrrolines, Application of 4,4-Diethoxybutan-1-amine, the publication is RSC Advances (2017), 7(80), 50955-50960, database is CAplus.

In this article, a novel tandem reaction, which transformed N-(4,4-diethoxybutyl)imines into 3-arylidene-1-pyrrolines, was described. The substrate scope of the starting acetals included arenes with electron-donating and withdrawing groups. The X-ray study of products confirmed the E-stereochem. of the double bonds formed. The best yields (99%) were found in boiling xylene in the presence of TsOH (or 2-nitroresocinol) during 40 (50) hours. The study of substituents effect on the course of the reaction revealed that cascade process took place, combining acid-catalyzed intramol. cyclization of N-(4,4-diethoxybutyl)imines and unusual 1,3-sigmatropic shift of the aryl fragment. Cyclic imines that were formed in high/excellent yields were of interest both from the viewpoint of their biol. activity and synthetic usefulness.

RSC Advances published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C6H12N2O, Application of 4,4-Diethoxybutan-1-amine.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts