Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives of myo-Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals

Tamboli Majid I.; Shashidhar Mysore S.; Gonnade Rajesh G.; Krishnaswamy Shobhana

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Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives of myo-Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals

机译：固态的肌醇碳酸盐和硫代碳酸盐衍生物的分子内环化：分子晶体中酰基转移反应的含义。

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Racemic 4-O-phenoxycarbonyl and 4-O-phenoxythiocarbonyl derivatives of myo-inositol orthoformate undergo thermal intramolecular cyclization in the solid state to yield the corresponding 4,6-bridged carbonates and thiocarbonates, respectively. The thermal cyclization also occurs in the solution and molten states, but less efficiently, suggesting that these cyclization reactions are aided by molecular pre-organization, although not strictly topochemically controlled. Crystal structures of two carbonates and a thiocarbonate clearly revealed that the relative orientation of the electrophile and the nucleophile in the crystal lattice facilitates the intramolecular cyclization reaction and forbids the intermolecular reaction. The correlation observed between the chemical reactivity and the non-covalent interactions in the crystal of the reactants provides a way to estimate the chemical stability of analogous molecules in the solid state.

机译：原肌醇肌醇的外消旋4-O-苯氧基羰基和4-O-苯氧基硫羰基衍生物在固态下经历热分子内环化，分别产生相应的4,6-桥联碳酸盐和硫代碳酸盐。热环化也发生在溶液和熔融状态，但是效率较低，这表明尽管没有严格的拓扑化学控制，这些环化反应还是由分子的预组织辅助的。两种碳酸盐和一种硫代碳酸盐的晶体结构清楚地表明，亲电体和亲核体在晶格中的相对取向促进了分子内环化反应并禁止了分子间反应。在化学反应性和反应物晶体中的非共价相互作用之间观察到的相关性提供了估算固态类似分子化学稳定性的方法。

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《Chemistry: A European journal》 |2015年第39期|共7页
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Tamboli Majid I.; Shashidhar Mysore S.; Gonnade Rajesh G.; Krishnaswamy Shobhana;
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正文语种 eng
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crystal engineering; cyclitols; inositols; nucleophilic substitution; solid-phase synthesis;

机译：晶体工程;环糖醇;肌醇;亲核取代;固相合成;

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1. Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives of myo-Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals [J] . Tamboli Majid I., Shashidhar Mysore S., Gonnade Rajesh G., Chemistry: A European journal . 2015,第39期

机译：固态的肌醇碳酸盐和硫代碳酸盐衍生物的分子内环化：分子晶体中酰基转移反应的含义。
2. Crystal and Molecular Structures of New chromone Derivatives as Empirical Evidence of Intramolecular Proton Transfer Reaction; Ab Initio Studies on Intramolecular H-Bonds in Enaminones [J] . Agnieszka J. Rybarczyk-Pirek, Slawomir J. Grabowski, Magdalena Malecka, The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory . 2002,第49期

机译：新型色酮衍生物的晶体和分子结构作为分子内质子转移反应的经验证据;烯胺内分子内H键的从头算研究
3. Creation of Concave-Shaped Conformation in Crystal Structures Using an Iminodicarbonyl Linker.An Application to Solid-State Intramolecular [4 + 4] Photocycloaddition Reactions of 2-Pyridone Derivatives [J] . Hyuma Masu, Ken Ohmori, Keiki Kishikawa, Bulletin of the Chemical Society of Japan . 2005,第6期

机译：亚胺二羰基连接体在晶体结构中形成凹形构象。2-吡啶酮衍生物在固态分子内[4 + 4]光环加成反应中的应用
4. Side chain-to-Side chain Cyclization by Intramolecular Click Reaction - Building Blocks, Solid Phase Synthesis and Conformational Characterization [C] . Soma Cantel, Jose A. Halperin, Michael Chorev American Peptide Symposium . 2009

机译：侧链到侧链通过分子内咔哒反应 - 构建块，固相合成和构象表征
5. Part 1: Lanthanum(III) Triflate-Catalyzed Cyclopropanation via Intramolecular Methylene Transfer Part 2: Reaction Design with Aromatic Ions - Nucleophilic Acyl Substitution and Organophotoredox Catalysts. [D] . Hardee, David James. 2011

机译：第1部分：通过分子内亚甲基转移的三氟甲磺酸镧（III）催化的环丙烷化作用第2部分：与芳香族离子的反应设计-亲核酰基取代和有机光氧化还原催化剂。
6. Intramolecular thermal reactions of the derivatives of 5′-azido-5′-deoxyuridine. A new feasible route to the regio- and stereospecific synthesis of reversed nucleosides carrying a substituted five-membered heterocycle [O] . Tadashi Sasaki, Katsumaro Minamoto, Toshimichi Suzuki, 1978

机译：5-叠氮基-5-脱氧尿苷衍生物的分子内热反应。带有取代的五元杂环的反向核苷的区域和立体特异性合成的新可行途径
7. Acyl-transfer reactions in molecular crystals: reactivity correlation with crystal structure [O] . Rajesh G. Gonnade, Mysore S. Shashidhar 2017

机译：分子晶体中的酰基转移反应：与晶体结构的反应性相关性

Intramolecular Cyclization of Carbonate and Thiocarbonate Derivatives of myo-Inositol in the Solid State: Implications for Acyl Group Transfer Reactions in Molecular Crystals

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