Design of novel chirality of macrocyclic compound bearing heteroaromatic biaryls

带有杂芳联芳基的大环化合物的新型手性设计

• 批准号: 24655083
• 负责人: MORI Atsunori
• 金额: $ 2.66万
• 依托单位: Kobe University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Challenging Exploratory Research
• 财政年份: 2012
• 资助国家: 日本
• 起止时间: 2012-04-01 至 2014-03-31
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-24655083/
• 关键词: 分子不斉; ヘテロ芳香族; キラルHPLC; CHホモカップリング; 閉環メタセシス; イミダゾール; チオフェン; X線結晶構造解析; ヘテロビアリール; 軸性不斉; ルテニウム触媒; 光学分割; ビスアゾール

Design of winding-vine-shaped organic molecule was carried out. The obtained compound was found to show molecular asymmetry, which is a molecule with no carbogenic chiral center. Imidazole derivatives as a nitrogen-containing heteroaromatic compound was subjected to CH homocoupling reaction and following ruthenium-catalyzed ring-closing metathesis leading to the compounds showing molecular asymmetry. The structure of the obtained molecule was confirmed by X-ray structure analysis and its chirality was revealed by HPLC analysis with a chiral column. Separation of both enantiomers were also achievled by the resolution with a preparative chiral column. The related compound of molecular asymmetry was also prepared with a thiophene derivative, which was a heteroaromatic compound bearing a sulfur atom.

进行了缠绕葡萄状有机分子的设计。发现获得的化合物显示出分子不对称性，该分子是没有碳纤维性手性中心的分子。咪唑衍生物作为含氮异源化合物的CH均耦合反应，并遵循氟苯甲状腺催化的环闭环节，从而导致表现出分子不对称的化合物。通过X射线结构分析证实了所获得的分子的结构，并通过手性柱通过HPLC分析揭示了其手性。通过制备性手性柱的分辨率也可以实现两个对映体的分离。还用硫苯衍生物制备了分子不对称的相关化合物，该硫烯衍生物是带有硫原子的杂虫化合物。

项目成果

軸性不斉イミダゾール骨格を有する大環状化合物の合成

轴不对称咪唑骨架大环化合物的合成

• 发表时间: 2013
• 作者: Shotaro Nishio;Takashi Somete;Atsushi Sugie;Tohru Kobayashi;Tsuyoshi Yaita;Atsunori Mori;Shotaro Nishio;Shinobu Mitsuda;森敦紀;岡山陽一,辻悟,西尾正太郎,染手隆志,杉江敦司,小林徹,矢板毅,森敦紀
• 通讯作者: 岡山陽一,辻悟,西尾正太郎,染手隆志,杉江敦司,小林徹,矢板毅,森敦紀

Synthesis and Properties of Regioregular Poly(3-substituted thiophene) Bearing Disiloxane Moiety in the Substituent. Remarkably High Solubility in Hexane

• DOI: 10.1246/cl.131222
• 发表时间: 2014-01
• 期刊: Chemistry Letters
• 影响因子: 1.6
• 作者: A. Mori;Kenji Ide;Shunsuke Tamba;S. Tsuji;Y. Toyomori;T. Yasuda

軸性不斉ビチオフェン骨格を有する大環状化合物の合成

轴不对称联噻吩骨架大环化合物的合成

• 发表时间: 2013
• 作者: Shotaro Nishio;Takashi Somete;Atsushi Sugie;Tohru Kobayashi;Tsuyoshi Yaita;Atsunori Mori;Shotaro Nishio;Shinobu Mitsuda;森敦紀;岡山陽一,辻悟,西尾正太郎,染手隆志,杉江敦司,小林徹,矢板毅,森敦紀;辻悟,光田紫乃布,岡山陽一,杉江敦司,小林徹,宮崎有史,矢板毅,森敦紀
• 通讯作者: 辻悟,光田紫乃布,岡山陽一,杉江敦司,小林徹,宮崎有史,矢板毅,森敦紀

ヘテロ芳香族化合物の触媒的カップリング 新反応開発から応用まで

杂芳族化合物的催化偶联：从新反应开发到应用

• 发表时间: 2013
• 作者: Shotaro Nishio;Takashi Somete;Atsushi Sugie;Tohru Kobayashi;Tsuyoshi Yaita;Atsunori Mori;Shotaro Nishio;Shinobu Mitsuda;森敦紀;岡山陽一,辻悟,西尾正太郎,染手隆志,杉江敦司,小林徹,矢板毅,森敦紀;辻悟,光田紫乃布,岡山陽一,杉江敦司,小林徹,宮崎有史,矢板毅,森敦紀;辻悟,光田紫乃布,岡山陽一,杉江敦司,森敦紀;Atsunori Mori;森 敦紀
• 通讯作者: 森 敦紀

ヘテロ芳香族化合物のCHカップリング反応新反応開発から応用まで

杂芳烃CH偶联反应从新反应开发到应用

• 发表时间: 2013
• 作者: Shotaro Nishio;Takashi Somete;Atsushi Sugie;Tohru Kobayashi;Tsuyoshi Yaita;Atsunori Mori;Shotaro Nishio;Shinobu Mitsuda;森敦紀
• 通讯作者: 森敦紀