9-heptyl-9H-fluorene | 98609-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-heptyl-9H-fluorene
• 英文别名: 9-heptyl-fluorene；9-Heptyl-fluoren；9H-Fluorene, 9-heptyl-
• CAS: 98609-93-9
• 化学式: C₂₀H₂₄
• 分子量: 264.411
• InChiKey: KPRIUJJIMJNBCL-UHFFFAOYSA-N

物化性质

• 沸点：
  172 °C(Press: 1 Torr)
• 密度：
  1.017 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-heptyl-9H-fluorene 在 硫酸 、 硝酸 作用下， 生成 9-heptyl-2,7-dinitro-fluorene
  参考文献：
  名称：

  Condensation of Aldehydes with Fluorene and Nirofluorenes

  摘要：

  DOI：

  10.1021/jo50005a005
• 作为产物：
  描述：

  芴 在 乙醇 、 potassium ethoxide 、 铂 、 xylene 作用下， 生成 9-heptyl-9H-fluorene
  参考文献：
  名称：

  Condensation of Aldehydes with Fluorene and Nirofluorenes

  摘要：

  DOI：

  10.1021/jo50005a005

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...
• The Base-catalyzed Alkylation of Fluorene with Alcohols
  作者：Kurt L. Schoen、Ernest I. Becker

  DOI：10.1021/ja01627a068

  日期：1955.11
• 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.