Solid-State Photodimerization of Methyl (<i>RS</i>)-1-Phenyl-2-piperidinoethyl (<i>RS</i>)-1,4-Dihydro-2,6-dimethyl-4-(2-thiazolyl)pyridine-3,5-dicarboxylate Hydrochloride Controlled by the Buffer Zone
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- Marubayashi Nobuhiro
- Research Laboratories, Yoshitomi Pharmaceutical Industries Ltd.
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- Ogawa Takayuki
- Research Laboratories, Yoshitomi Pharmaceutical Industries Ltd.
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- Hirayama Noriaki
- Department of Biological Science and Technology, Tokai University
書誌事項
- タイトル別名
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- Solid-State Photodimerization of Methyl (RS)-1-Phenyl-2-piperidinoethyl (RS)-1,4-Dihydro-2,6-dimethyl-4-(2-thiazolyl)pyridine-3,5-dicarboxylate Hydrochloride Controlled by the Buffer Zone.
- Solid-State Photodimerization of Methyl
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抄録
The solid-state photodimerization of three polymorphic crystal forms (forms I, II, and III) of a bulky olefin, methyl (RS)-1-phenyl-2-piperidinoethyl (RS)-1,4-dihydro-2,6-dimethyl-4-(2-thiazolyl)pyridine-3,5-dicarboxylate hydrochloride, was studied. Forms I and II are anhydrous crystals and form III is an isomorphous hydrate of form II. X-Ray analyses of these forms showed that forms II and III have the same geometrical characteristics suggesting high susceptibility to photodimerization according to the well-known topochemical rule. Although UV irradiation of from II affords a photodimer, 4a,8a-dimethoxycarbonyl-2,4b,6,8b-tetramethyl-3-[(RS)-1-phenyl-2-piperidinoethoxycarbonyl]-7-[(SR)-1-phenyl-2-piperidinoethoxycarbonyl]-(4RS,8SR)-4,8-di(2-thiazolyl)-1,4,4a,4b,5,8,8a,8b-octahydro-cis-transoid-4a,4b-cis-cyclobuta[1,2-b : 3,4-b′]dipyridine, in high yield, the photolysis of form III proceeds much more slowly than that of form II. A detailed inspection of the crystal structures revealed that there is a space to afford the mobility of molecules for dimerization in form II, whereas the space is occupied by the incorporated water molecule in form III. We have previously proposed that a buffer zone, which is a space in the crystal structure, controls the photodimerization of bulky olefins. The present study demonstrates that the buffer zone is an essential controlling factor for the solid-state photodimerization of bulky olefins.
収録刊行物
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 71 (2), 321-327, 1998
公益社団法人 日本化学会
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詳細情報 詳細情報について
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- CRID
- 1390001204121306752
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- NII論文ID
- 130004149986
- 10008928322
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- NII書誌ID
- AA00580132
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- ISSN
- 13480634
- 00092673
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- NDL書誌ID
- 4406049
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
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