2-(芴-9-亚基甲基)噻吩 | 843638-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 2-(芴-9-亚基甲基)噻吩
• 英文名称: 2-((9H-fluoren-9-ylidene)methyl)thiophene
• 英文别名: 2-Fluoren-9-ylidenemethylthiophene；2-(fluoren-9-ylidenemethyl)thiophene
• CAS: 843638-98-2
• 化学式: C₁₈H₁₂S
• 分子量: 260.359
• InChiKey: PXFBPSLHTWGNSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(芴-9-亚基甲基)噻吩 在 吡啶 、 sodium azide 、 盐酸羟胺 、 三乙胺盐酸盐 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 34.5h， 生成 2-[5-(9H-fluoren-9-ylidenemethyl)thiophen-2-yl]-5-(naphthalen-2-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Theoretical and experimental study of donor-bridge-acceptor system: model 2-[5-(9H-fluoren-9-ylidenemethyl)thiophen-2-yl]-1,3,4-oxadiazole derivatives

  摘要：

  The theoretical study of the titled model acceptor-bridge-donor molecular series based on 9H-fluoren-9-ylidenemethyl and 1,3,4-oxadiazole heterocycles is presented. The subunits are linked through a thienyl moiety, and the second alpha-site of oxadiazole was modified. The quantum chemical model indicated that the electron-donating properties of 9H-fluoren-9-ylidenemethyl were significantly supported or suppressed by the terminal substitution of 1,3,4-oxadiazole which affected the possible semiconductivity. Finally, the possible synthesis of selected molecules is described, and the prepared derivatives were fully characterized by H-1 NMR, C-13 NMR, IR, and elemental analysis together with optical and electrochemical measurements.

  DOI：

  10.1007/s00706-016-1843-2
• 作为产物：
  描述：

  2-噻吩甲醛 、 芴 在 potassium hydroxide 作用下， 以 甲苯 为溶剂， 生成 2-(芴-9-亚基甲基)噻吩
  参考文献：
  名称：

  连续工艺下 Amberlyst-A26 介导的 9-亚烷基-9H-芴的 Corey-Chaykovsky 环丙烷化反应

  摘要：

  在此，我们开发了一种连续工艺，使用三甲基碘化亚砜作为亚甲基源，在 Amberlyst-A26 作为非均相碱存在下，通过 Corey-Chaykovsky 环丙烷化反应直接环丙烷化各种不与羰基共轭的烯烃。几种 9-亚烷基-9 H-芴衍生物在连续工艺模块下成功进行 Corey-Chaykovsky 环丙烷化，以优异的产率提供螺[环丙烷-1,9'-芴]。此外，还描述了使用 Amberlyst-A26 作为多相碱对 3-亚苄基二氢吲哚-2-酮衍生物进行环丙烷化的连续方法，得到螺[环丙烷-1,3'-二氢吲哚]-2'-酮衍生物。

  DOI：

  10.1021/acs.joc.3c02260

文献信息

• Synthesis of 9-Fluorenylidenes via Pd-Catalyzed C–H Vinylation with Vinyl Bromides
  作者：Shuai Yang、Yanghui Zhang

  DOI：10.1021/acs.orglett.1c02722

  日期：2021.10.15

  A facile and efficient approach for the synthesis of 9-fluorenylidenes has been developed via the palladium-catalyzed cross-coupling of 2-iodobiphenyls and vinyl bromides. The reaction involves the C–H activation of 2-iodobiphenyls and dual C–C bond formations. A range of 9-fluorenylidene derivatives, including diphenyldibenzofulvenes, can be synthesized with the reaction.

  通过钯催化的 2-碘联苯和乙烯基溴的交叉偶联，开发了一种简便有效的合成 9-芴基的方法。该反应涉及 2-碘联苯的 C-H 活化和双 C-C 键的形成。通过该反应可以合成一系列 9-芴基衍生物，包括二苯基二苯并富烯。
• Palladium-catalyzed coupling reaction of 2-iodobiphenyls with alkenyl bromides for the construction of 9-(diorganomethylidene)fluorenes
  作者：Ya-Heng Zhao、Jian-Long Wang、Yun-Bing Zhou、Miao-Chang Liu、Hua-Yue Wu

  DOI：10.1039/d1ob01547h

  日期：——

  protocol for the construction of 9-(diorganomethylidene)fluorenes through palladium-catalyzed coupling reactions of 2-iodobiphenyls with alkenyl bromides has been reported. The reaction proceeds through the C–H activation/oxidative addition/reduction elimination/intramolecular Heck coupling reaction to afford a series of 9-(diorganomethylidene)fluorenes with good yields. Control experiments demonstrate that

  已经报道了通过钯催化的 2-碘联苯与烯基溴的偶联反应构建 9-（二有机亚甲基）芴的原子经济协议。该反应通过C-H活化/氧化加成/还原消除/分子内Heck偶联反应进行，以良好的收率得到一系列9-(二有机亚甲基)芴。对照实验表明，五元钯环作为关键中间体，β-H 消除作为限速步骤。
• Manganese catalyzed switchable <i>C</i>-alkylation/alkenylation of fluorenes and indene with alcohols
  作者：Avijit Mondal、Rahul Sharma、Debjyoti Pal、Dipankar Srimani

  DOI：10.1039/d1cc03529k

  日期：——

  central goal in catalysis. This would be especially interesting when the reactivity and selectivity patterns can be tuned. Herein, we introduced the first Mn-catalyzed selective C-alkylation and olefination of fluorene, and indene with alcohols. Various substrates including benzylic, heteroaromatic, and aliphatic primary and secondary alcohols are employed as alkylating agents. Mechanistic investigations

  使用地球上丰富的、无毒的过渡金属代替稀有贵金属是催化的中心目标。当可以调整反应性和选择性模式时，这将特别有趣。在此，我们首次介绍了 Mn 催化的芴和茚与醇的选择性C-烷基化和烯化。包括苄醇、杂芳族和脂肪族伯醇和仲醇在内的各种底物被用作烷化剂。机理研究和动力学研究支持烯化中间体的参与以提供烷基化产物。
• Synthesis of Benzo[<i>b</i>]fluoranthenes and Spiroacridines from Fluorene-Derived Alkenes and <i>N</i>-Arylimines via a Tandem Reaction with Benzynes
  作者：Weihua Wang、Hongwei Wan、Guangfen Du、Bin Dai、Lin He

  DOI：10.1021/acs.orglett.9b00659

  日期：2019.5.17

  Two tandem processes involving the cycloaddition of benzynes have been developed for the synthesis of polyaromatic hydrocarbons. Benzynes react with fluorene-derived alkenes through a tandem Diels–Alder reaction/dehydrogenation process to afford benzo[b]fluoranthenes in 35–87% yields. In addition, an unprecedented [2 + 2] cycloaddition/ring-opening sequence of benzynes and fluorene-derived N-arylimines

  已经开发了涉及联苯的环加成的两个串联方法来合成聚芳族烃。通过串联Diels-Alder反应/脱氢过程，苯并zy与芴衍生的烯烃反应，以35-87％的收率得到苯并[ b ]芴。此外，前所未有的[2 + 2]苯并炔和芴衍生的N-芳基嘧啶的环加成/开环顺序可轻松获得螺cr啶，收率为38-79％。
• New Synthesis of Dibenzofulvenes by Palladium-Catalyzed Double Cross-Coupling Reactions
  作者：Masaki Shimizu、Ikuhiro Nagao、Shin-ichi Kiyomoto、Tamejiro Hiyama

  DOI：10.1071/ch12060

  日期：——

  Palladium-catalyzed double cross-coupling reactions of 1,1-bis(pinacolato)borylalk-1-enes with 2,2′-dibromobiaryls and of 9-stannafluorenes with 1,1-dibromoalk-1-enes have been demonstrated to serve as new synthetic methods for dibenzofulvenes.

  已证明钯催化的1,1-双（频哪醇）硼烷基-1-烯与2,2'-二溴联芳基和9-芴与1,1-二溴烷基-1-烯的双交叉偶联可以用作二苯并富勒烯的新合成方法。