每周分子 | Molecule of the Week
点击上方， 订阅话题 ，不错过每周分子！
每周分子：Cylindricine H
Molecule of the Week:
Cylindricine H
Cylindricines类化合物包括十一种海洋生物碱。1993-1995年间，塔斯马尼亚大学(霍巴特校区，澳大利亚)的科学家Adrian J. Blackman及合作者从海鞘1(Clavelina cylindrica)中分离出了Cylindricines类化合物。所有Cylindricines类化合物的相似之处在于它们均含有三环吡咯结构或吡咯并[1，2-j]喹啉结构，但又具有不同的官能团(C=C, C=O, -Cl, -OH, -OMe, -OAc, -SCN或-NCS)和烷基侧链(正丁基或正己基)。
科学家们还没有弄清所有Cylindricines类化合物的立体化学结构或在实验室完成了全合成。今年七月，科学家Mercedes Amat与巴塞罗那大学的合作者们报道了(-)-Cylindricine H的全合成工作，(-)-Cylindricine H同时具有乙酸酯和硫氰酸酯官能团。
据作者描述，立体选择性的关键步骤是在C10位形成季碳立体中心；在C4位引入乙酰氧基，以及在C2位引入丁基；并且以正确的构象组装吡咯烷环和硫氰酸甲基。
由于Cylindricine H并非商业化产品，其危害信息尚未被披露。
1. 也称为被囊动物，一种无脊椎海洋动物。
Cylindricine H信息速览
【关于每周分子】
自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的SciFinder中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。
The cylindricines are a group of 11 marine alkaloids that were isolated off the coast of Tasmania from the ascidian1Clavelina cylindrica between 1993 and 1995 by Adrian J. Blackman and co-workers at the University of Tasmania (Hobart). All the cylindricines have similar tricyclic pyrrolo- or pyrido[1,2-j]quinoline structures with varying functional groups (C=C, C=O, -Cl, -OH, -OMe, -OAc, -SCN, and/or -NCS) and alkyl side chains (n-butyl or n-hexyl).
Not all the cylindricines have fully worked-out stereochemistry or have been totally synthesized in the lab. But this past July, Mercedes Amat and co-workers at the University of Barcelona reported the total synthesis of (–)-cylindricine H, which has both acetate and thiocyanate functionalities.
According to the authors, the key stereoselective steps were the generation of a quaternary stereocenter at C10; the introduction of the acetoxy group at C4 and the butyl group at C2; and the assembly of the pyrrolidine ring with the thiocyanatomethyl group in the proper configuration.
Because cylindricine H is not a commercial product, no hazard information has been reported.
1. Also known as a tunicate, an invertebrate sea animal.
Cylindricine Hfast facts
About Molecule of the Week
MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.
每周分子Molecule of the Week：胍丁胺每周分子Molecule of the Week：雌四醇每周分子Molecule of the Week：丙戊酸每周分子Molecule of the Week：二硫化钯每周分子Molecule of the Week：胭脂红酸每周分子Molecule of the Week：阿朴吗啡每周分子Molecule of the Week：聚己双胍每周分子Molecule of the Week：甲基苯基缩水甘油酸乙酯每周分子Molecule of the Week：2-糠硫醇
每周分子Molecule of the Week：双三氟甲基磺酰亚胺锂每周分子Molecule of the Week：枯茗醛每周分子Molecule of the Week：苯甲酸乙酯和对异丙基甲苯每周分子Molecule of the Week：2-乙酰-1-吡咯啉每周分子Molecule of the Week：香芹酮每周分子Molecule of the Week：柠檬烯
每周分子Molecule of the Week：L-赖氨酸每周分子Molecule of the Week：丁酸钠每周分子Molecule of the Week：亚硒酸钠每周分子Molecule of the Week：二甲基亚砜每周分子Molecule of the Week：闭式-二碳十二硼烷每周分子Molecule of the Week：氟伏沙明
每周分子Molecule of the Week：四氟铍酸铵每周分子Molecule of the Week：氯甲烷每周分子Molecule of the Week：三硒化锑每周分子Molecule of the Week：D-阿洛酮糖每周分子Molecule of the Week：十二硼酸铯每周分子Molecule of the Week：松萝酸每周分子Molecule of the Week：五氯苯酚
每周分子Molecule of the Week：氟化氢每周分子Molecule of the Week：乙醇胺
每周分子Molecule of the Week：磷化锌每周分子Molecule of the Week：弗虫腈每周分子Molecule of the Week：尿胆素每周分子Molecule of the Week：庙宇烷每周分子Molecule of the Week：异丁腈每周分子Molecule of the Week：檀香醇每周分子Molecule of the Week：氯氟磺酰每周分子Molecule of the Week：1,2-异亚丙基甘油每周分子Molecule of the Week：氯法齐明每周分子Molecule of the Week：四甲基硅烷每周分子Molecule of the Week：印楝素每周分子Molecule of the Week：马兜铃酸每周分子Molecule of the Week：三磷酸腺苷每周分子Molecule of the Week：钙钛矿每周分子Molecule of the Week：正十二面体烷每周分子Molecule of the Week：抗坏血酸每周分子Molecule of the Week：氨每周分子Molecule of the Week：氯化十六烷基吡啶每周分子Molecule of the Week：槟榔碱每周分子Molecule of the Week：1,6-萘吡啶每周分子Molecule of the Week：尿素每周分子Molecule of the Week：双环辛四烯合铀每周分子Molecule of the Week：苯甲酸每周分子Molecule of the Week：角鲨烯每周分子Molecule of the Week：1H-1,2,3-三唑
每周分子Molecule of the Week：尿酸每周分子Molecule of the Week：2-乙酰基呋喃、2-乙酰基吡咯每周分子Molecule of the Week：硼烷-四氢呋喃每周分子Molecule of the Week：硬脂酸钠每周分子Molecule of the Week：4-甲氧基苯乙烯每周分子Molecule of the Week：硫化锌每周分子Molecule of the Week：螺旋内酯甾酮每周分子Molecule of the Week：白磷每周分子Molecule of the Week：紫杉醇每周分子Molecule of the Week：吡啶每周分子Molecule of the Week：正硅酸四乙酯每周分子Molecule of the Week：Zoliflodacin每周分子Molecule of the Week：Azidoazide azide每周分子Molecule of the Week：苯炔每周分子Molecule of the Week：D-葡萄糖胺每周分子Molecule of the Week：胍每周分子Molecule of the Week：地塞米松每周分子Molecule of the Week：六氟-2-丁烯每周分子Molecule of the Week：磁铁矿每周分子Molecule of the Week：氢气每周分子Molecule of the Week：蒽每周分子Molecule of the Week：EIDD-2801每周分子Molecule of the Week：四氯化碳每周分子Molecule of the Week：硼化铑
每周分子Molecule of the Week：铱络合物阳离子八聚体每周分子Molecule of the Week：去甲肾上腺素每周分子Molecule of the Week：氯霉素每周分子Molecule of the Week：氮化硼每周分子Molecule of the Week：镍钐氧化物每周分子Molecule of the Week：瑞德西韦每周分子Molecule of the Week：土臭素每周分子Molecule of the Week：二亚乙基三胺
每周分子Molecule of the Week：龙涎香醇每周分子Molecule of the Week：巴利替尼每周分子Molecule of the Week：二硫化钼每周分子 | Molecule of the Week：过氧乙酰硝酸酯每周分子Molecule of the Week：比马前列素每周分子 | Molecule of the Week：二氧化钒每周分子 | Molecule of the Week: 比马前列素每周分子 | Molecule of the Week：2-氰基丙烯酸乙酯每周分子 | Molecule of the Week：丁酸庚酯每周分子 | Molecule of the Week：丙烯酰胺每周分子 | Molecule of the Week: 氯酸钾每周分子 | Molecule of the Week：12-羟基硬脂酸锂每周分子 | Molecule of the Week：二烷基二硫代磷酸锌每周分子 | Molecule of the Week：熊去氧胆酸每周分子 | Molecule of the Week：糠醛每周分子 | Molecule of the Week：环氧乙烷每周分子 | Molecule of the Week：硝酸甘油每周分子 | Molecule of the Week：阿斯巴甜每周分子 | Molecule of the Week: 反式肉桂醛每周分子 | Molecule of the Week：Trivertal每周分子 | Molecule of the Week：甲醛次硫酸氢鈉每周分子 | Molecule of the Week：麦克风每周分子 | Molecule of the Week：缩水甘油每周分子 | Molecule of the Week：二恶烷四酮
每周分子 | Molecule of the Week：呋喃妥因每周分子 | Molecule of the Week：并四苯每周分子 | Molecule of the Week: 两性霉素B每周分子 | Molecule of the Week：肌苷每周分子 | Molecule of the Week：D-葡萄糖酸每周分子 | Molecule of the Week：糖精
每周分子 | Molecule of the Week：靛玉红每周分子 | Molecule of the Week: 二氧化銥每周分子 | Molecule of the Week: 硼烯每周分子 | Molecule of the Week：苦杏仁苷及其衍生物Laetrile每周分子 | Molecule of the Week：氦化氢每周分子 | Molecule of the Week: 白杨素和哈尔满每周分子 | Molecule of the Week：阿维巴坦钠每周分子 | Molecule of the Week：氟哌啶醇每周分子 | Molecule of the Week：2-己基肉桂醛每周分子 | Molecule of the Week：大蒜烯每周分子 | Molecule of the Week：替莫唑胺每周分子 | Molecule of the Week：二氢左旋葡萄糖酮每周分子 | Molecule of the Week：甲苯每周分子 | Molecule of the Week：乙酸乙酯每周分子 | Molecule of the Week：二氯甲烷每周分子 | Molecule of the Week：拉罗替尼每周分子 | Molecule of the Week：叶绿素每周分子 | Molecule of the Week： 苯乙腈葡糖苷每周分子Molecule of the Week：红花菜豆酸每周分子Molecule of the Week：盐酸氮卓斯汀每周分子Molecule of the Week：(+)-乙酸龙脑酯每周分子Molecule of the Week：阿波霉素δ2每周分子Molecule of the Week：L-半胱氨酸每周分子Molecule of the Week：磷烷每周分子Molecule of the Week: 莫西菌素每周分子Molecule of the Week：L-丙氨酸和L-丝氨酸每周分子Molecule of the Week: N,N-二甲基色胺每周分子Molecule of the Week：米拉贝隆每周分子Molecule of the Week：2,4-二硫杂戊烷每周分子 Molecule of the Week: 尼古丁每周分子 Molecule of the Week：透明质酸每周分子Molecule of the Week：羟苯甲酮和桂皮酸盐每周分子Molecule of the Week：苄青霉素每周分子Molecule of the Week: 水仙环素每周分子Molecule of the Week: 富勒烯
每周分子Molecule of the Week: 甜菊糖每周分子Molecule of the Week: 布洛芬
每周分子Molecule of the Week：月桂酸和肉豆蔻酸每周分子Molecule of the Week：索菲布韦每周分子Molecule of the Week：Cucurbitacins每周分子Molecule of the Week：Fluralaner
点击“阅读原文”
你“在看”我吗？