Bis(2,5-dimethoxy-4-methylphenyl)methane and bis(2,5-dimethoxy-3,4,6-trimethylphenyl)methane

Wiedenfeld, David; Нестеров, В. Н.; Minton, Mark A.; Glass, David R.

doi:10.1107/s0108270103024673

Cited by 4 publications

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“…The majority of para-anisole derivatives have a CÐOÐCÐC angle close to planarity (< 15 or > 165 ), with a signi®cant difference in their OÐCÐC angles that can be attributed to steric and electronic effects. Two related examples have been reported by Wiedenfeld et al (2003).…”

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confidence: 89%

“…The MeO group at atom C14 displays an OÐCÐC distortion, with O3Ð C14ÐC13/C15 angles of 115.60 (13) and 123.34 (13) (transoid to atom C13 and the C 5 chain). These distortions, especially that of the C Me ÐOÐCÐC torsion-angle orientation with respect to the OÐCÐC angle, have been commented on previously (Bruno et al, 2001;Gallagher et al, 2001;Wiedenfeld et al, 2003).…”

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confidence: 99%

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tert-Butyl 5-methoxy-3-pentylindole-1-carboxylate

2004

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The molecule of the title compound, C 19 H 27 NO 3 , is essentially planar, with all non-H atoms within 0.2 A Ê of the ninemembered indole plane, except for the three tert-butyl C atoms. The C 5 pentyl chain is in an extended conformation, with three torsion angles of 179.95 (13), 179.65 (13) and À178.95 (15) (the latter two angles include the C atoms of the C 5 chain only). Three intramolecular CÐHÁ Á ÁO C contacts are present (CÁ Á ÁO < 3.05 A Ê and CÐHÁ Á ÁO > 115 ), and an intermolecular CÐHÁ Á ÁO C contact and %±% stacking complete the intermolecular interactions. CommentThe key biochemical roles played by the indole ring in nature ensure that this heterocyclic system continues to attract scrutiny from medicinal and synthetic chemists. It is a common motif for drug targets and, as such, the development of new diversity-tolerant routes to this privileged biological scaffold continues to be of signi®cant bene®t (Gribble, 1996) and forms the basis of a wide variety of drugs, including the antiin¯ammatory agent Indomethacin, Reserpine (exploited as a hypotensive agent) and Sumatriptan (used for the treatment of migraine). Historically, interest in indoles arose from the isolation and characterization of indole alkaloids, which, along with their semi-synthetic derivatives, have potent central nervous system activity. Many recent advances in indole synthesis have focused on metal-mediated procedures, with copper, palladium, tin, titanium and zirconium being the most prevalent (Sundberg, 1996;Gribble, 2000).Recently, we reported a new approach to the synthesis of the indole scaffold, exploiting a controlled organolithium addition to functionalized styrenes, with the CÐC bond formation reaction as the key synthetic step. A signi®cant bene®t of this strategy is that it can provide a direct route for the introduction of further structural diversity onto the ring system (Coleman & O'Shea, 2003), which may be of bene®t for combinatorial library generations. Despite the prevalence of indole structures in the Cambridge Structural Database (CSD; Allen, 2002), there are no structures that contain the indole skeleton and atoms substituted at the 1-(C), 3-(C) and 5-positions (O) for direct comparison with the title compound, (I). However, many derivatives that contain the tryptophan residue are present in the CSD.Pertinent bond lengths and angles for (I) are listed in Table 1 and the molecular structure is depicted in Fig. 1. The bond lengths and angles are as expected for indole systems (Fig. 1). Localization in the aromatic rings is discernible in (I), with a C1AÐC2A bond length of 1.3481 (19) A Ê [the other NC 4 -ring CÐC lengths are 1.4496 (19) and 1.4090 (18) A Ê ], and CÐN distances of 1.4022 (16) and 1.4076 (18) A Ê ; in the C 6 ring, the C13ÐC14 and C15ÐC16 bond lengths are 1.379 (2) and 1.386 (2) A Ê , respectively. In the C 5 pentyl chain, the CÐC bond lengths for atoms C1±C5 are in the narrow range 1.509 (2)±1.5195 (19) A Ê ; the C2AÐC1ÐC2 angle opens to 114.98 (12) , and the remaining CÐCÐC angles along the c...

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confidence: 89%

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tert-Butyl 5-methoxy-3-pentylindole-1-carboxylate

2004

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“…For the out-of-plane methoxy group, C6ÐO1ÐC7 and C3ÐO2ÐC9 are distinctly lower, at 114.7 (3) in (IIIa) and 113.6 (3) in (IIIb). We have previously found such effects in related compounds (Wiedenfeld et al, 2003(Wiedenfeld et al, , 2004. Such geometry is usual for compounds containing OCH 3 groups with different orientations about aromatic rings (Gallagher et al, 2001).…”

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confidence: 75%

1-Chloro-3,6-dimethoxy-2,5-dimethylbenzene and 1-chloro-3,6-dimethoxy-2,4-dimethylbenzene

et al. 2004

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The title compounds, 1-chloro-3,6-dimethoxy-2,5-dimethylbenzene, (IIIa), and 1-chloro-3,6-dimethoxy-2,4-dimethylbenzene, (IIIb), both C10H13ClO2, were obtained from 2,5- and 2,6-dimethyl-1,4-benzoquinone, respectively, and are intermediates in the synthesis of ammonium quinone derivatives. The isomers have different substituents around the methoxy groups and crystallize in different space groups. In both molecules, the methoxy groups each have different orientations with respect to the benzene ring. In both cases, one methoxy group lies in the plane of the ring and can participate in conjugation with the aromatic system, while the second is almost perpendicular to the plane of the aromatic ring. The C-O-C bond angles around these substituents are also different: 117.5 (4) and 118.2 (3) degrees in (IIIa) and (IIIb), respectively, when the methoxy groups lie in the plane of the ring, and 114.7 (3) and 113.6 (3) degrees in (IIIa) and (IIIb), respectively, when they are out of the plane of the ring.

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“…Structures of compounds with 2,5-dimethoxy-3,4,6-trimethyl-substituted benzene rings are rare with only two entries (Wickramasinhage et al, 2016;Wiedenfeld et al, 2003) found in the CSD (Version 5.37, November 2015 with three updates; Groom et al 2016).…”

Section: Structure Descriptionmentioning

confidence: 99%

Methyl 3-(2,5-dimethoxy-3,4,6-trimethylphenyl)propanoate

et al. 2017

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In the title compound, C15H22O4, the fully substituted benzene ring carries a methyl propanoate, two methoxy and three methyl substituents. Both methoxy substituents are almost orthogonal to the benzene ring plane. The methyl propanoate group is almost planar, r.m.s. deviation 0.0138 Å, and is inclined to the benzene ring plane by 80.26 (14)°. In the crystal, C—H...O hydrogen bonds form head-to-tail chains of molecules along theb-axis direction that are supported by very weak C—H...π(ring) contacts.

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Bis(2,5-dimethoxy-4-methylphenyl)methane and bis(2,5-dimethoxy-3,4,6-trimethylphenyl)methane

Cited by 4 publications

References 3 publications

tert-Butyl 5-methoxy-3-pentylindole-1-carboxylate

tert-Butyl 5-methoxy-3-pentylindole-1-carboxylate

1-Chloro-3,6-dimethoxy-2,5-dimethylbenzene and 1-chloro-3,6-dimethoxy-2,4-dimethylbenzene

Methyl 3-(2,5-dimethoxy-3,4,6-trimethylphenyl)propanoate

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