Claims
- 1. A compound of the formula ##STR9## wherein W is NO.sub.2, NH.sub.2 ; R.sup.1, R.sub.2 and R.sub.3 can be independently selected from the group consisting of H, lower alkyl, aryl, aralkyl, halogen, or cyano; R.sup.1 and R.sup.2 may not both be aryl; and n is 0, 2 or 3.
- 2. A compound as described in claim 1 wherein n is 1.
- 3. 4-[1-(3aminopropyl)]-4-[1-(3-hydroxypropyl)]-1,7-heptanediol.
- 4. 4-amino-4-[1-(3-hydroxypropyl)]-1,7-heptanediol.
TECHNICAL FIELD
This application is a continuation of application Ser. No. 401,323, filed Aug. 31, 1989, now abandoned.
This invention relates to the chemical field of aminoalkyltriols in general and to the chemical field of bis-homotris compounds in particular. It also relates to the synthons used in the preparation of a novel class of micelles or cascade polymers. It further concerns the preparation and usefulness of a group of chemicals which permit the creation of multifunctional, multitiered cascade polymers.
Micelles, which have many biotechnological uses, may be constructed as unimolecular structures with cascade methodology utilizing a series of chemical reactions in which building block molecules of the effective structure ##STR1## are reacted to form inter amide bonds between amino and carboxyl groups of different molecules. Initial cascade polymers have been shown to form aqueous [Newkome et al., J. Chem. Soc., Chem. Commun., 1986, 752] and non-aqueous [Baker, G.R., Dissertation, L.S.U., 1989] gels which possess properties suitable to a diverse range of applications which include, but are not limited to, bacteriological, growth, microscopy media, cosmetics and toiletries, drilling muds for oil production, textile printing (such as dye paste), foods, glazes, inks, lattices, lubricants, paints, pharmaceuticals, and agricultural [Molynenx, P., Chemistry and Technology of Water-Soluable Polymers; Plenum: New York, 1983, 113-114].
The literature indicates a number multi-armed and/or polybranched compounds, which include polypods, [Fornasier et al., Tet. Lett., 1976, 1381 and Vogtle et al., Chem. Ber., 1979, 112, 899]; hydrophillic lipids [Heiman and Vogtle, Annalen, 1980, 858]; octapus and hexapus molecules [Murakami et al., J. Chem. Soc., Perkin 1, 1981, 2800]; tentacle molecules [Suckling, C. J., J. Chem. Soc., Chem. Commun., 1982, 661] hexahost [MacNicol et al., J. Chem. Soc., Chem. Commun., 1976, 494]; branched polyamines [Geue et al., Aust. J. Chem., 1983 36, 927]; many-armed acyclic polyethers [Vogtle et al., Angew. Chem., Int. Eng. Ed., 1974, 13, 814]; starburst-dentritic macromolecules [Tomalia et al., Polym. J., 1985, 17, 117]; starburst polyether dendrimers [Hall, Tomalia et al., J. Org. Chem., 1987, 52, 5305]; noncyclic polyaza compounds [Vogtle et al., Synth., 1978, 155], and U.S. Pat. No. 4,507,466, issued Mar. 26, 1985. However, such compounds are: 1) difficult to prepare as evidenced by the required harsh conditions, 2) insufficiently soluble in aqueous solutions for some applications, 3) irregular in their molecular construction, and 4) susceptible to decomposition under mild conditions (in some instances yield, or include, toxic by-products).
Due to their unique construction, the new monomeric compounds of the present invention circumvents these problems by allowing mild functional group interconversion and alkylation, with even sterically demanding nucleophiles, of the building block termini. Specifically, the three carbon distance, which each terminus is displaced from the quaternary carbon center of branching, makes this possible. The literature indicates a lesser distance of separation to be unacceptable for nucleophilic substitution at multiple reaction sites equidistant from a center of branching [Rice et al., J. Pharm. Sci., 1971, 60, 1760].
The juxtaposition of reactive site termini relative to branching points in the invention allows the preparation of new cascade polymers based on a multiplicative and repetitive methodology which incorporates amidation, functional group interconversion, and alkylation (nucleophilic substitution) [Newkome et al., J. Am. Chem. Soc., 1986, 108, 849 and Newkome et al., J. Org. Chem., 1985, 50, 2003].
Therefore, an object of this invention is to provide novel compositions of matter which are useful as synthons or "building blocks" for cascade polymers.
Another object of this invention is the usefulness of new aminotriols as pH buffers in aqueous solution. This is due to the functional equivalency of the aminotriols to tris(hydroxymethyl) aminomethane which is employed extensively as a pH buffer.
This invention is comprised of the new compositions of matter and methods for the preparation of compounds of the structures ##STR2## These compounds are important intermediates for the synthesis of the desired cascade building blocks (Newkome, Moorefield, and Theriot, J. Org. Chem., 1988, 53, 5552).
More broadly, however, this invention claims novel compounds of the formula ##STR3## wherein
W is
R.sup.2 and R.sup.3 may be the same or different;
R.sup.1 and R.sup.2 may not both be aryl;
X is
Z is
R.sup.1 is
R.sup.2 and R.sup.3 may be the same or different;
X is
Z is
Y is
US Referenced Citations (16)
Foreign Referenced Citations (1)
| Number |
Date |
Country |
| 1511911 |
Dec 1967 |
FRX |
Non-Patent Literature Citations (7)
| Entry |
| Rice et al., Journal of Pharmaceutical Sciences, vol. 60(11), p. 1760 (1971). |
| Newcome et al., J. Org. Chem. vol. 53, No. 23, pp. 5552-5554, (1988). |
| Krasnovskii et al., Chem. Abstracts 104:171364s (1986). |
| Index Chemicus, 17, 50586 (1965). |
| Heathcock et al., "A Stereoselective Total Synthesis of the Guaiazulenic Sesquiterpenoids .alpha.-Bulnesene and Bulnesol," Apr. 7, 1971, J. Chem Soc. |
| Ono et al, "DenitroHydrogenation of Aliphatic Nitro Compounds and New Use of Aliphatic Nitro Compounds as Radical Precursors," 1985, Tetrahedron, vol. 41, No. 19, pp. 4013-4023. |
| Brown et al., "Reaction of Diborane in Tetrahydrofuran Unit Selected Organic Compounds Containing Representative Functional Groups," Mar. 25, 1970, J. Chem. Soc. |
Continuations (1)
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Number |
Date |
Country |
| Parent |
401323 |
Aug 1989 |
|
Patent Grant
5136096
