Organocascade Synthesis of Bicyclo[3.3.1] nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones

Wang De-Chih; Huang Pin-Han; Huang Wan-Wun; Cheng You-Song; Chen Kwunmin

首页> 外文期刊>Advanced synthesis & catalysis >Organocascade Synthesis of Bicyclo[3.3.1] nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones

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Organocascade Synthesis of Bicyclo[3.3.1] nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones

机译：有机可口血基合成的双环[3.3.1]由不寻常的1,6-加入环己酮（E）-2-（3-芳基甲苯）-1H-茚-1,3（2H） - 二氧化硫而引发的壬酮-9-壬烯-9-诺-9-诺 - 9-诺 - 9- in-9--1

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An efficient organocatalytic cascade reaction for the synthesis of the bicyclo[3.3.1] nonan-9-one skeleton is reported. The cascade reaction proceeds smoothly between prochiral 4-substituted cyclohexanones and (E)-2-(3-arylallylidene)-indene1,3-diones involving a 1,6-/gamma-protonation/1,4-addition sequence to construct bicyclic products that contain five stereogenic centers in good to high chemical yields and excellent diastereo- and enantioselectivity (up to > 20: 1 dr and 97% ee) in the presence of a thioether-linked l-prolinol-camphor-derived organo-catalyst at ambient temperature. An interesting organocatalytic three-component triple cascade reaction has been performed to produce a bicyclo[2.2.2] octan-2-one in a favorable chemical yield and stereoselectivity (> 19: 1 dr and 97% ee) starting from 1,3-indanedione, an enal, and cyclohexenone in the presence of a primary amine organocatalyst.

机译：报道了一种有效的有机催化级联反应，用于合成双环[3.3.1]壬烃-9-一骨架。级联反应在普通4-取代的环己酮和（e）-2-（3-芳基甲苯） - 吲哚1,3-致偏转物之间平稳地进行，涉及1,6- /γ-质子/ 1,4-加成序列以构建双环制品在硫醚连接的L-脯酚酚蛋白 - 樟脑催化剂存在下，含有五种立体含量和优异的高分体和对映选择性（高达> 20：1和97％的EE）在环境中的含量良好温度。已经进行了一个有趣的有机催化三分组分三重级联反应，以获得有利的化学产率和立体选择性（> 19：1博士和97％ee）的辛西环辛烷-2- odan-2-1。从1,3-开始在伯胺有机催化剂存在下，indanedione，肿瘤和环己酮。

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来源
《Advanced synthesis & catalysis》 |2017年第17期|共9页
作者
Wang De-Chih; Huang Pin-Han; Huang Wan-Wun; Cheng You-Song; Chen Kwunmin;
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Natl Taiwan Normal Univ Dept Chem Taipei 11677 Taiwan;

Natl Taiwan Normal Univ Dept Chem Taipei 11677 Taiwan;

Natl Taiwan Normal Univ Dept Chem Taipei 11677 Taiwan;

Natl Taiwan Normal Univ Dept Chem Taipei 11677 Taiwan;

Natl Taiwan Normal Univ Dept Chem Taipei 11677 Taiwan;

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正文语种 eng
中图分类化学工业;物理化学（理论化学）、化学物理学;化学反应过程;
关键词
bicyclic compounds; cascade reaction; enantioselectivity; organocatalysis; vinylogous process;

机译：双环化合物;级联反应;对映选择性;有机成分分析;乙烯基工艺;

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专利

1. Organocascade Synthesis of Bicyclo[3.3.1] nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones [J] . Wang De-Chih, Huang Pin-Han, Huang Wan-Wun, Advanced synthesis & catalysis . 2017,第17期

机译：有机可口血基合成的双环[3.3.1]由不寻常的1,6-加入环己酮（E）-2-（3-芳基甲苯）-1H-茚-1,3（2H） - 二氧化硫而引发的壬酮-9-壬烯-9-诺-9-诺 - 9-诺 - 9- in-9--1
2. Twin applications of highly selective Cu2+ fluorescent chemosensor and cytotoxicity of 2-(2-phenylhydrazono)-1H-indene-1,3(2H)-dione and 2-(2-(4-methoxyphenyl)hydrazono)-1H-indene-1,3(2H)-dione: molecular docking and DFT studies [J] . Subhasri Annamalai, Anbuselvan Chinnadurai, Rajendraprasad Nagarajen RSC Advances . 2014,第105期

机译：高选择性Cu2 +荧光化学传感器的两次应用和2-（2-苯基hydr] -1H-茚-1,3（2H）-二酮和2-（2-（4-甲氧基苯基）hydr] -1H-茚-1的细胞毒性，3（2H）-dione：分子对接和DFT研究
3. Stereoselective synthesis of substituted bicyclo-[3.3.1]-nonan-9-ones by additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one [J] . Andrew RJ., Reid G., Mellor JM. Tetrahedron . 2000,第37期

机译：通过将环己酮的烯胺加到4-乙氧基-1,1,1-三氟丁-3-烯-2-酮中的立体选择性合成取代的双环-[3.3.1]-壬南-9-酮
4. Glassy 2-(1-benzyl-2-styryl-6-methylpyridin-4(1-H)-ylidene) fragment containing 1H-indene-1,3(2H)-dione and pyrimidine-2,4,6(1H,3H,5H)-trione derivatives with light-emitting and amplified spontaneous emission properties [C] . Elmars Zarins, Julija Pervenecka, Elina Misina, Conference on Fiber Lasers and Glass Photonics: Materials through Applications . 2020

机译：含1H-茚-1,3（2H）-二酮和嘧啶-2,4,6（1H）的玻璃状2-（1-苄基-2-苯乙烯基-6-甲基吡啶-4（1-H）-亚烷基）片段具有发光和放大的自发发射特性的3H，5H）-三酮衍生物
5. Crystal structures, syntheses, and spectroscopic and electrochemical measurements of two push–pull chromophores: 2-4-(dimethylamino)benzylidene-1H-indene-1,3(2H)-dione and (E)-2-{3-4-(dimethylamino)phenylallylidene}-1H-indene-1,3(2H)-dione [O] . Georgii Bogdanov, John P. Tillotson, Tatiana Timofeeva 2019

机译：两个推拉式发色团的晶体结构，合成和光谱和电化学测量：2- 4-（二甲基氨基）苄基 -1H-茚-1,3（2H） - 二氧化乙烯和（E）-2- {3- 4-（二甲基氨基）苯基烯丙基丙烯} -1H-茚-1,3（2H） - 二氧化乙烯

Organocascade Synthesis of Bicyclo[3.3.1] nonan-9-ones Initiated by an Unusual 1,6-Addition of Cyclohexanones to (E)-2-(3-Arylallylidene)-1H-indene-1,3(2H)-diones

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