1-(m-tolylethynyl)cyclobutan-1-ol

Silver-initiated radical ring expansion/fluorination of ethynyl cyclobutanols: efficient synthesis of monofluoroethenyl cyclopentanones

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC02656G, Communication

Qingshan Tian, Bin Chen, Guozhu Zhang
A stereoselective synthesis of [small beta]-halogenated 2-methylenecyclopentanones via silver-catalyzed formal ring expansion using water as the cosolvent is described.

Silver-initiated radical ring expansion/fluorination of ethynyl cyclobutanols: efficient synthesis of monofluoroethenyl cyclopentanones

Qingshan Tian,^a   Bin Chen^a and   Guozhu Zhang*^a  

*

Corresponding authors

^a

State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China
E-mail: guozhuzhang@sioc.ac.cn

Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC02656G

A stereoselective synthesis of β-halogenated 2-methylenecyclopentanones via silver-catalyzed formal ring expansion using water as the cosolvent is described. A variety of 2-methylenecyclopentanones with fluoro, chloro and bromo functionalities are efficiently prepared from 1-alkynyl cyclobutanols. This method offers facile access to halogenated complex molecules which are not only useful chemicals but also valuable building blocks for further derivatizations.

1-(m-tolylethynyl)cyclobutan-1-ol (1b) Yield: 89%; Yellow oil;

1H NMR (400 MHz, CDCl3)

δ 7.25 (s, 1H), 7.23 (d, J = 8.1 Hz, 1H), 7.18 (t, J = 7.5 Hz, 1H), 7.10 (d, J = 7.5 Hz, 1H), 2.51 (dt, J = 15.8, 6.3 Hz, 2H), 2.34 (t, J = 9.3 Hz, 2H), 2.30 (s, 3H), 1.85 (m, 2H);

13C NMR (100 MHz, CDCl3)

δ 137.94, 132.27, 129.19, 128.72, 128.17, 122.49, 92.16, 83.58, 68.31, 38.64, 21.20, 12.98; HRMS (EI+ , 70 eV): C13H14O [M]+ : calcd. 186.1045, found 186.1047

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Valdetamide

CAS Registry Number: 512-48-1

CAS Name: 2,2-Diethyl-4-pentenamide

Additional Names: diethylallylacetamide

Trademarks: Novonal (Hoechst)

Molecular Formula: C9H17NO

Molecular Weight: 155.24

Percent Composition: C 69.63%, H 11.04%, N 9.02%, O 10.31%

Literature References: Description: Bockmühl, Schaumann, Dtsch. Med. Wochenschr. 54, 270 (1928). Pharmacokinetics and metabolism: H. Uehleke, M. Brinkschulte-Freitas, Arch. Pharmacol. 302, 11 (1978). TLC determn in urine: E. Klug, P. Toffel, Arzneim.-Forsch. 29, 1651 (1979).

Properties: White powder, mp 75-76°. Sol in 120 parts water; freely sol in alcohol, ether.

Melting point: mp 75-76°

Therap-Cat: Sedative, hypnotic.

Keywords: Sedative/Hypnotic; Amides.

Valdetamid (Valdetamide)

Structural formula

UV - spectrum

Conditions : Concentration - 50 mg / 100 ml
The solvent designation schedule	methanol	Water	0.1 M HCl	0.1M NaOH
maximum absorption	-	-	-	-
	-	-	-	-
ε	-	-	-	-

IR - spectrum

Wavelength (μm)
Wave number (cm -1 )

Range
10 largest peaks:
Peak	53	55	57	67	69	81	112	126	127	140
Value	152	848	115	141	929	156	286	999	338	238

References

• UV and IR Spectra. H.-W. Dibbern, RM Muller, E. Wirbitzki, 2002 ECV
• NIST / EPA / NIH Mass Spectral Library 2008
• Handbook of Organic Compounds. NIR, IR, Raman, and UV-Vis Spectra Featuring Polymers and Surfactants, Jr., Jerry Workman.Academic Press, 2000.
• Handbook of ultraviolet and visible absorption spectra of organic compounds, K. Hirayama. Plenum Press Data Division, 1967.

Brief background information

Salt	ATC	Formula	MM	CAS
-	N05C	C 9 H 17 NO	155.24 g / mol	512-48-1

Using

• hypnotic

Classes substance

• Amides

Synthesis Way

Synthesis of a)

Trade names

A country	Tradename	Manufacturer
Germany	Arantxa	Hoechst
	Betadorm-H	Woelm
	insomnia	ICN
	Nokturetten	Starke
	New Dolestan	Much
Ukraine	no	no

Formulations

• dragees 50 mg;
• 300 mg Tablets

References

• DRP 473 329 (IG Farben; appl 1925.).
• DRP 616 876 (IG Farben; appl 1930.).
• DRP 622 875 (IG Farben; appl 1931.).
• GB 253,950 (IG Farben; appl 1926;.. D-prior 1925).

1H NMR PREDICT

Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC02396G, Communication

Gopal Chandru Senadi, Ganesh Kumar Dhandabani, Wan-Ping Hu, Jeh-Jeng Wang
We have identified metal-free reaction conditions for the annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines to the corresponding acridine derivatives.

Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

Gopal Chandru Senadi,^a   Ganesh Kumar Dhandabani,^a  Wan-Ping Hu^b and   Jeh-Jeng Wang*^a  

*Corresponding authors

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shiquan 1st Rd, Sanmin District, Kaohsiung City, Taiwan
E-mail: jjwang@kmu.edu.tw

^bDepartment of Biotechnology, Kaohsiung Medical University, No. 100, Shiquan 1st Rd, Sanmin District, Kaohsiung City, Taiwan

Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC02396G, 

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC02396G?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Gopal Chandru Senadi

Kaohsiung Medical University

Department of Medicinal and Applied Chemistry

Kaohsiung, Taiwan

link......click

We have identified metal-free reaction conditions for the annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines to the corresponding acridine derivatives. The combination of trifluoroacetic acid (TFA), tert-butyl hydroperoxide (TBHP), dimethylsulfoxide (DMSO) and oxygen (O₂) converted the cyclohexanone derivatives to an aromatic aryl product in moderate to good yields. The experimental results suggest that this process involves an aza-allyl oxidation intermediate.

Prof. Jeh-Jeng Wang

Professor
Department of Medicinal and Applied Chemistry
Kaohsiung Medical University
Kaohsiung, Taiwan

Lab: N842, Bioorganic chemistry Laboratory
Email: jjwang@kmu.edu.tw
Tel: +886-7-3121101
Fax: 886-7-3125339

Click here to see my official Faculty page at KMU

Click here to email me

Prof. Jeh-Jeng Wang

Education: B.S., Chemistry, National Chung-Hsing University, Taiwan (1975-1979) Ph.D., Chemistry, The Ohio State University, USA (1983-1989) Career: Teaching Assistant, National Chung-Hsing University, Taiwan (1981-1983) Postdoctoral fellow, College of Pharmacy, University of Texas, Austin, USA (1989-1991) Associate Professor, Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Taiwan (1991-2001) Professor, Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Taiwan (since 2001)

 click on imageclick on image

3aa as a pale yellow solid (234 mg, 92%); m.p. 181-182 ° C; IR (neat)max: 1362 cm -1; 1 H NMR (400 MHz, CDCl3) δ 8.31 (d, J = 8.8 Hz, 2H), 7.76 (ddd, J = 8.0, 6.8, 1.6 Hz, 2H), 7.72 (d, J = 8.8 Hz, 2H), 7.66 – 7.56 (m, 3H), 7.49 – 7.41 (m, 4H);

13C NMR (101 MHz, CDCl3) δ 148.66, 147.24, 135.85, 130.37, 129.96, 129.45, 128.40, 128.31, 12

1H NMR

 

13 c nmr

 

//////////Metal-free annulatio, erobic oxidative dehydrogenation, cyclohexanones, o-acylanilines, acridines

Prof. J.J. Wang birthday party - October 21, 2016


Department of Medicinal and Applied Chemistry
Kaohsiung Medical University





Kaohsiung, TAIWAN

Kaohsiung

Municipality in Taiwan

Kaohsiung is a massive port city in southern Taiwan. It's home to many skyscrapers, such as the 248m-tall Tuntex Sky Tower, and is known for its diversity of parks. Its focal point is the Love River, with walking paths and cafes along its banks, and cruise boats navigating its waters. Shopping options range from high-end malls to the Liuhe and Ruifeng night markets

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