9-cyclopentyl-9H-fluorene | 76390-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-cyclopentyl-9H-fluorene
• 英文别名: 9-cyclopentyl-fluorene；9-Cyclopentyl-fluoren
• CAS: 76390-49-3
• 化学式: C₁₈H₁₈
• 分子量: 234.341
• InChiKey: HUNMKXXKFPDTLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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-cyclopentylidene-9H-fluorene 在 sodium periodate 、 一水合肼 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 以30%的产率得到9-cyclopentyl-9H-fluorene
  参考文献：
  名称：

  Praefcke, Klaus; Weichsel, Christian, Liebigs Annalen der Chemie, 1980, # 10, p. 1604 - 1619

  摘要：

  DOI：

文献信息

• 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...
• 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，
• Unravelling a bench-stable zinc-amide compound as highly active multitasking catalyst for radical-mediated selective alk(en)ylation of unactivated carbocycles under mild conditions
  作者：Sangita Sahoo、Subarna Manna、Arnab Rit

  DOI：10.1039/d3sc06334h

  日期：——

  compound bearing an amidated imidazolium salt towards C–C bond-forming reactions utilizing an array of alcohols, ranging from aliphatic to aromatic and, attractively, even secondary alcohols. Moreover, this readily scalable protocol, which proceeds via an underdeveloped radical-mediated borrowing hydrogen protocol (an aldehyde is generated from an alcohol, and subsequent condensation with indene/fluorene

  通过C-C 键形成对未活化的有机部分进行直接官能化长期以来一直令合成化学家着迷。尽管贱金属系统在该领域稳步兴起，但在单一催化剂中实现多任务活性以在温和条件下执行多个此类功能化是具有挑战性的。为了解决这个问题，我们在此报告了一种有效的方案，首次使用天然丰富且环保的锌衍生化合物，用醇作为绿色烷化剂对茚/芴进行选择性C-烷（烯）基化。值得注意的是，这项研究揭示了带有酰胺化咪唑鎓盐的稳定锌化合物在使用一系列醇（从脂肪族到芳香族，甚至仲醇）进行C-C键形成反应方面的独特潜力。此外，这种易于扩展的方案通过基于一系列对照实验建立的不发达的自由基介导的借氢方案（由醇产生醛，随后与茚/芴缩合提供相应的烯基化产物）进行，有效在温和条件下使用低催化剂负载即可轻松实现。值得注意的是，这种方法对烷基化或烯基化产物具有显着的选择性，具有高水平的官能团耐受性和化学选择性。至关重要的是，这些锌化合物的催化活性可归因于它们
• Notes - The Base-Catalyzed Alkylation of Flourene with Secondary Alcohols
  作者：D. Matthews、Ernest Becker

  DOI：10.1021/jo01117a614

  日期：1956.11
• Zn(II)‐Stabilized Azo‐Anion Radical Catalyzed Sustainable C−C Bond Formation: Regioselective Alkylation of Fluorene, Oxindole, and Indoles
  作者：Subhasree Pal、Amit Kumar Guin、Subhajit Chakraborty、Nanda D. Paul

  DOI：10.1002/cctc.202400026

  日期：2024.5.21

  Herein we report a sustainable approach for the alkylation of ketones, 9H‐fluorene, oxindole, and indole using alcohols as the alkylating agent catalyzed by a well‐defined air‐stable zinc catalyst (1 a) of a tridentate redox non‐innocent arylazo ligand, 2‐((4‐chlorophenyl)diazenyl)‐1,10‐phenanthroline (La). 2–3 mol % of 1 a efficiently produces substituted α‐alkylated ketones, 9‐alkylated fluorenes, C3‐alkylated oxindoles, and C3‐alkylated indoles in moderate to good isolated yields. In aerial condition, the formation of bis(indolyl)methane (BIMs) derivatives were observed when indoles were subjected to alkylation by primary alcohols. A few drug molecules containing BIMs were prepared in good isolated yields. The catalyst 1 a exhibited good chemoselectivity during the functionalization of fluorene and indole with oleyl alcohol and β‐citronellol. A few control experiments, including deuterium labeling experiments, performed to unveil the reaction mechanism indicate that the one‐electron reduced azo‐anion radical species [1 a]‐formed in situ, acts as the active catalyst. All the redox events occur at the redox‐active aryl‐azo ligand, which acts as the reservoir of hydrogen and electrons throughout the catalytic cycle, keeping the Zn(II)‐center as a template.