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Synthesis and Crystal Structure of 3-Quinuclidinyl α-(Cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate

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Abstract

The title compound 3-quinuclidinyl α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate was obtained by the reaction of methyl α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate with 3-quinuclidinol in n-heptane. Its structure was characterized by 1H, 13C NMR, MS and X-ray single-crystal diffraction techniques: C20H25NO3, M r = 327.41, orthorhombic, space group P212121 with a = 8.547(2), b = 11.428(4), c = 18.288(5) Å, V = 1786.3(9) Å3, Z = 4. The title compound comprises a tertiary α-hydroxy acid and a bicyclo[2.2.2]octan moiety. The crystal structure shows the presence of the intermolecular O(1)–H(1)···N(1) hydrogen bonds.

Index Abstract

The title compound, 3-quinuclidinyl α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate was obtained by the reaction of methyl α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate with 3-quinuclidinol in n-heptane and its crystal structure determined. The title compound comprises a tertiary α-hydroxy acid and a bicyclo[2.2.2]octan moiety. The crystal structure shows the presence of the intermolecular O(1)–H(1)···N(1) hydrogen bonds.

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Scheme 1
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Authors and Affiliations

  1. College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang, 050016, People’s Republic of China

    Yu-min Liu & Yong-qi Hu

  2. No. 7 Department, Beijing Institute of Pharmacology and Toxicology, Beijing, 100850, People’s Republic of China

    He Liu

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  1. Yu-min Liu
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  2. He Liu
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  3. Yong-qi Hu
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Correspondence to He Liu.

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Liu, Ym., Liu, H. & Hu, Yq. Synthesis and Crystal Structure of 3-Quinuclidinyl α-(Cyclopentyl-1-ene)-α-hydroxy-α-phenylacetate. J Chem Crystallogr 38, 491–494 (2008). https://doi.org/10.1007/s10870-008-9395-x

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  • DOI: https://doi.org/10.1007/s10870-008-9395-x

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