SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 8, 2008, Pages 1219-1221

Short synthesis of a specifically perdeuterated hexaethylene glycol terminated alkanethiol

(4) Jogireddy, Rajamalleswaramma a,b Zawisza, Izabella a Wittstock, Günther a Christoffers, Jens a

a UNIVERSITY OF OLDENBURG (Germany)

b UNIVERSITÉ DE STRASBOURG (France)

Author keywords

Alkanethiol; Mercaptane; Oligo(ethylene glycol); Self assembled monolayer; Thiourea

Indexed keywords

ALKANETHIOL; GLYCOL; HEXAETHYLENE GLYCOL; THIOL; THIOL DERIVATIVE; THIOUREA;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; MONOLAYER CULTURE; SYNTHESIS;

EID: 44349158863 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072731 Document Type: Article

Times cited : (7)

References (27)

1
- 0028338446
- (a) Singhvi, R.; Kumar, A.; Lopez, G. P.; Stephanopoulos, G. N.; Wang, D. I.; Whitesides, G. M.; Ingber, D. E. Science 1994, 264, 696.
- (1994) Science , vol.264 , pp. 696
- Singhvi, R.¹ Kumar, A.² Lopez, G.P.³ Stephanopoulos, G.N.⁴ Wang, D.I.⁵ Whitesides, G.M.⁶ Ingber, D.E.⁷

2
- 0001338169
- (b) Mrksich, M. Chem. Soc. Rev. 2000, 29, 267.
- (2000) Chem. Soc. Rev , vol.29 , pp. 267
- Mrksich, M.¹

3
- 4544383503
- (c) Raghavan, S.; Chen, C. S. Adv. Mater. 2004, 16, 1303.
- (2004) Adv. Mater , vol.16 , pp. 1303
- Raghavan, S.¹ Chen, C.S.²

4
- 2142702936
- (d) Li, N.; Tourovskaia, A.; Folch, A. Crit. Rev. Biomed. Eng. 2003, 31, 423.
- (2003) Crit. Rev. Biomed. Eng , vol.31 , pp. 423
- Li, N.¹ Tourovskaia, A.² Folch, A.³

5
- 33847060069
- (e) Girard, P. P.; Cavalcanti-Adam, E. A.; Kemkemer, R.; Spatz, J. P. Soft Matter 2007, 3, 307.
- (2007) Soft Matter , vol.3 , pp. 307
- Girard, P.P.¹ Cavalcanti-Adam, E.A.² Kemkemer, R.³ Spatz, J.P.⁴

6
- 0030953763
- Chen, C. S.; Mrksich, M.; Huang, S.; Whitesides, G. M.; Ingber, D. E. Science 1997, 276, 1425.
- (1997) Science , vol.276 , pp. 1425
- Chen, C.S.¹ Mrksich, M.² Huang, S.³ Whitesides, G.M.⁴ Ingber, D.E.⁵

7
- 0032077443
- (a) Folch, A.; Toner, M. Biotechnol. Prog. 1998, 14, 388.
- (1998) Biotechnol. Prog , vol.14 , pp. 388
- Folch, A.¹ Toner, M.²

8
- 0034646334
- (b) Chiu, D. T.; Jeon, N. L.; Huang, S.; Kane, R. S.; Wargo, C. J.; Choi, I. S.; Ingber, D. E.; Whitesides, G. M. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 2408.
- (2000) Proc. Natl. Acad. Sci. U.S.A , vol.97 , pp. 2408
- Chiu, D.T.¹ Jeon, N.L.² Huang, S.³ Kane, R.S.⁴ Wargo, C.J.⁵ Choi, I.S.⁶ Ingber, D.E.⁷ Whitesides, G.M.⁸

9
- 0026351910
- (a) Prime, K. L.; Whitesides, G. M. Science 1991, 252, 1164.
- (1991) Science , vol.252 , pp. 1164
- Prime, K.L.¹ Whitesides, G.M.²

10
- 0043210642
- (b) Herrwerth, S.; Eck, W.; Reinhardt, S.; Grunze, M. J. Am. Chem. Soc. 2003, 125, 9359.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 9359
- Herrwerth, S.¹ Eck, W.² Reinhardt, S.³ Grunze, M.⁴

11
- 33748653787
- Zhao, C.; Witte, I.; Wittstock, G. Angew. Chem. Int. Ed. 2006, 45, 5469;
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 5469
- Zhao, C.¹ Witte, I.² Wittstock, G.³

12
- 44349164829
- Angew. Chem. 2006, 118, 5595.
- (2006) Angew. Chem , vol.118 , pp. 5595

13
- 44349140930
- We actually presume a Br,O-acetal formation by a radical mechanism followed by hydrolysis.
- We actually presume a Br,O-acetal formation by a radical mechanism followed by hydrolysis.

14
- 0001728364
- (a) Buffeteau, T.; Desbat, B.; Turlet, J. M. Appl. Spectrosc. 1991, 45, 380.
- (1991) Appl. Spectrosc , vol.45 , pp. 380
- Buffeteau, T.¹ Desbat, B.² Turlet, J.M.³

15
- 34548526372
- (b) Zawisza, I.; Wittstock, G.; Boukherroub, R.; Szunerits, S. Langmuir 2007, 23, 9303.
- (2007) Langmuir , vol.23 , pp. 9303
- Zawisza, I.¹ Wittstock, G.² Boukherroub, R.³ Szunerits, S.⁴

16
- 44349117690
- Dissertation; Universität Heidelberg: Germany
- Herrwerth, S. Dissertation; Universität Heidelberg: Germany, 2002.
- (2002)
- Herrwerth, S.¹

17
- 0002754017
- (a) Pale-Grosdemange, C.; Simon, E. S.; Prime, K. L.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 12.
- (1991) J. Am. Chem. Soc , vol.113 , pp. 12
- Pale-Grosdemange, C.¹ Simon, E.S.² Prime, K.L.³ Whitesides, G.M.⁴

18
- 12044254336
- (b) Prime, K. L.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 10714.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 10714
- Prime, K.L.¹ Whitesides, G.M.²

19
- 33244475138
- (a) Saalmink, M.; van der Marel, C.; Stapert, H. R.; Burdinski, D. Langmuir 2006, 22, 1016.
- (2006) Langmuir , vol.22 , pp. 1016
- Saalmink, M.¹ van der Marel, C.² Stapert, H.R.³ Burdinski, D.⁴

20
- 33748519934
- (b) Nagahori, N.; Nishimura, S.-I. Chem. Eur. J. 2006, 12, 6478.
- (2006) Chem. Eur. J , vol.12 , pp. 6478
- Nagahori, N.¹ Nishimura, S.-I.²

21
- 0345245747
- (a) Boksanyi, L.; Liardon, O.; Kovats, E. Sz. Helv. Chim. Acta 1976, 59, 717.
- (1976) Helv. Chim. Acta , vol.59 , pp. 717
- Boksanyi, L.¹ Liardon, O.² Kovats, E.S.³

22
- 0032550650
- (b) Flink, S.; Boukamp, B. A.; van den Berg, A.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Am. Chem. Soc. 1998, 120, 4652.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 4652
- Flink, S.¹ Boukamp, B.A.² van den Berg, A.³ van Veggel, F.C.J.M.⁴ Reinhoudt, D.N.⁵

23
- 44349096078
- 22 ed, Wiley-VCH: Weinheim
- Schwetlick, K. Organikum, 22 ed.; Wiley-VCH: Weinheim, 2004.
- (2004) Organikum
- Schwetlick, K.¹

24
- 20444385835
- Canaria, C. A.; Smith, J. O.; Yu, C. J.; Fraser, S. E.; Lansford, R. Tetrahedron Lett. 2005, 46, 4813.
- (2005) Tetrahedron Lett , vol.46 , pp. 4813
- Canaria, C.A.¹ Smith, J.O.² Yu, C.J.³ Fraser, S.E.⁴ Lansford, R.⁵

25
- 44349110446
- Hexaethylene glycol (12-bromododecyl) ether (3a) NaH (145 mg, 3.63 mmol, 60% dispersion in mineral oil) was added portionwise to a solution of 1 (6.00 g, 21.3 mmol) in abs. DMF (60 mL) at 23°C. After the reaction mixture was stirred for 1 h, 2a (1.20 g, 3.66 mmol) was added and the resulting mixture stirred for 17 h at the same temperature. Then it was diluted with Et2O (100 mL) and washed with H2O (50 mL, After the separation of the organic layer, the aqueous layer was extracted with Et 2O (2 x 25 mL, The combined organic layers were dried over MgSO 4, filtered, and concentrated. The crude product was purified by column chromatography [SiO2, CH2Cl2-MeOH (15:1, Rf, 0.37] to obtain compound 3a (800 mg, 42, as a colorless liquid. IR (ATR, 3440 (m, 2926 (s, 2856 (s, 1675 (vs, 1460 (m, 1387 (m, 1256 (m, 1094 (vs, 946 (w, 733 (w, 660 (m) cm-1
- + + H]: 553.4246; found: 553.4245.

26
- 44349105071
- Hexaethylene glycol (12-bromododecyl) methyl ether (4a) A solution of MeI (2.60 g, 18.3 mmol) in abs. DMF (12 mL) was added to a cooled solution of NaH (55 mg, 1.38 mmol, 60% dispersion in mineral oil) in abs. DMF (12 mL) at -5°C After 15 min, a solution of alcohol 3a (487 mg, 0.920 mmol) in abs. DMF (12 mL) was added dropwise at -5°C and the mixture was stirred for 3.5 h at the same temperature. Few drops of MeOH were added and the resulting mixture was poured into a mixture of ice-cold H2O (5 mL) and Et 2O (10 mL, After layers were separated, the aqueous layer was extracted with Et2O (2 x 10 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography [SiO2, CH 2Cl2-MeOH (24:1, Rf, 0.50] to obtain compound 4a (430 mg, 86, as a colorless liquid. IR (ATR, 2925 s, 2860
- + + H]: 567.4403; found: 567.4403.

27
- 44349180057
- Hexaethylene glycol (12-thiododecyl) methyl ether (5a) A solution of bromide 4a (418 mg, 0.768 mmol) and thiourea (65 mg, 0.853 mmol) in EtOH (0.2 mL) was degassed (freeze, pump, thaw) and refluxed under N2 for 6 h. After cooling to 23°C, NaOH (0.5 mL, c, 5 mol L -1, aqueous solution) was added. The solution was again degassed (freeze, pump, thaw) and slowly heated to reflux. After refluxing for 2 h under N2 atmosphere, it was cooled to 23°C, acidified with HCl (1 mL, c, 2 mol L-1) and diluted with CH2Cl2 (1 mL, The layers were separated and the aqueous layer was extracted with CH2Cl2 (3 x 1 mL, The combined organic layers were washed with sat. aq NaHCO3 solution (1 mL, dried over MgSO4, filtered, and evaporated in vacuo. The crude product was purified by column chromatography [SiO2, CH2Cl2-MeOH 24:1
- + + H]: 521.5018; found: 521.5018.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.