9-(4-bromobenzyl)-9H-fluorene | 16305-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-(4-bromobenzyl)-9H-fluorene
• 英文别名: 9-(4-Bromobenzyl)fluorene；9-[(4-bromophenyl)methyl]-9H-fluorene
• CAS: 16305-98-9
• 化学式: C₂₀H₁₅Br
• 分子量: 335.243
• InChiKey: PIBMMIJPNSDLKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  9-(4-bromobenzylidene)-9H-fluorene 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 9-(4-bromobenzyl)-9H-fluorene
  参考文献：
  名称：

  Lavie; Bergmann, Bulletin de la Societe Chimique de France, 1951, p. 250,253

  摘要：

  DOI：

文献信息

• Nickel-catalyzed synthesis of 9-monoalkylated fluorenes from 9-fluorenone hydrazone and alcohols
  作者：Jiang-Tao Fan、Xin-Heng Fan、Yong-Jie Chen、Cai-Yan Gao、Lian-Ming Yang

  DOI：10.1080/00397911.2019.1647438

  日期：——

  Abstract A practical protocol was disclosed for the nickel-catalyzed C-alkylation of 9-fluorenone hydrazone with alcohols using t-BuOK as the base, and 9-monoalkylated fluorene derivatives were obtained in good yields under the benign conditions. GRAPHICAL ABSTRACT

  摘要 公开了一种以t-BuOK为碱，镍催化9-芴酮腙与醇C-烷基化的实用方案，并在良性条件下以良好的收率获得了9-单烷基化芴衍生物。图形概要
• Aldehyde/ketone-catalyzed highly selective synthesis of 9-monoalkylated fluorenes by dehydrative C-alkylation with primary and secondary alcohols
  作者：Jianhui Chen、Yang Li、Shuangyan Li、Jianping Liu、Fei Zheng、Zhengping Zhang、Qing Xu

  DOI：10.1039/c6gc02518h

  日期：——

  By using aldehydes or ketones as the catalyst and screening CsOH out as the more effective base than KOH in many instances, an efficient 9-C-alkylation of fluorenes with alcohols was...

  在许多情况下，通过使用醛或酮作为催化剂，并筛选出CsOH作为比KOH更有效的碱，芴与醇的有效9-C-烷基化反应...
• 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。
• <i>t</i>-BuOK-catalysed alkylation of fluorene with alcohols: a highly green route to 9-monoalkylfluorene derivatives
  作者：Jiang-Tao Fan、Xin-Heng Fan、Cai-Yan Gao、Zhenpeng Wang、Lian-Ming Yang

  DOI：10.1039/c9ra07557g

  日期：——

  A simple, mild and efficient protocol was developed for the alkylation of fluorene with alcohols in the presence of t-BuOK as catalyst, affording the desired 9-monoalkylfluorenes with near quantitative yields in most cases.

  开发了一种简单、温和且高效的方案，用于在t -BuOK 作为催化剂的情况下用醇对芴进行烷基化，在大多数情况下以接近定量的产率提供所需的 9-单烷基芴。
• Ligand-assisted nickel catalysis enabling sp³ C–H alkylation of 9<i>H</i>-fluorene with alcohols
  作者：Ayanangshu Biswas、Amreen K. Bains、Debashis Adhikari

  DOI：10.1039/d2cy00638c

  日期：——

  Herein we report a nickel-catalyzed sp3 C–H alkylation protocol of 9H-fluorene using cheap and abundant alcohols as the source of alkyl groups. The developed method spans a host of primary, secondary, aliphatic and alicyclic alcohols as the alkylation partner and exhibits chemoselectivity during alkylation. The alkylated products were synthesized in moderate to high yields that can rival those of a

  在这里，我们报告了镍催化的 9 H sp 3 C-H 烷基化方案-芴使用廉价和丰富的醇作为烷基来源。所开发的方法涵盖了许多伯醇、仲醇、脂肪醇和脂环醇作为烷基化伙伴，并在烷基化过程中表现出化学选择性。烷基化产物以中等至高产率合成，可与少数其他金属催化工艺相媲美。该烷基化反应中的重要中间体之一是 9-亚烷基芴，它经过加氢得到最终产物。该过程以配体为主并遵循自由基途径，这与所有先前烷基化芴的方法明显不同。为了展示氢储存在配体骨架中，