6-fluoro-3-methylphenanthrene | 84194-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 6-fluoro-3-methylphenanthrene
• 英文别名: 3-Fluoro-6-methylphenanthrene
• CAS: 84194-33-2
• 化学式: C₁₅H₁₁F
• 分子量: 210.251
• InChiKey: IIVOKFHMSIJKHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-fluoro-3-methylphenanthrene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 碘 、 sodium 、 三苯基膦 作用下， 以 四氯化碳 、 xylene 为溶剂， 反应 2.0h， 生成 trans-3-(2-chlorostyryl)-6-fluorophenanthrene
  参考文献：
  名称：

  Photocyclization of stilbenes. VII. Unusual fluorine atom rearrangement in the photocyclization of 1-fluoro[5]helicenes

  摘要：

  DOI：

  10.1021/jo00152a022
• 作为产物：
  描述：

  4-fluoro 4'-methyl stilbene 在 碘 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 以96%的产率得到6-fluoro-3-methylphenanthrene
  参考文献：
  名称：

  Expeditious synthesis of fluorinated styrylbenzenes and polyaromatic hydrocarbons

  摘要：

  A series of fluorinated styrylbenzene derivatives were synthesized by the Mizoroki-Heck reaction using phosphine-free catalytic conditions or by adopting the one-pot Wittig-Heck reaction sequence. The fluorinated styrylbenzenes were converted into polyaromatic hydrocarbons such as phenanthrenes, [4]helicenes, and benzo[ghi]perylene by a modified photocyclization procedure involving I-2-THF condition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.022

文献信息

• Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels–Alder Reaction/Aromatization
  作者：Vikram Singh、Ram Subhawan Verma、Anil K. Khatana、Bhoopendra Tiwari

  DOI：10.1021/acs.joc.9b01644

  日期：2019.11.1

  A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the

  已开发出一种高效的无过渡金属的通用方法，该方法可从β-溴乙烯基芳烃和芳烃中合成诸如菲和菲（及四苯）之类的多环芳烃。该反应通过芳烃Diels-Alder（ADA）反应进行，然后进行容易的芳构化。这是有关使用ADA方法直接构建车菊（和四苯酚）的第一份报告。与仅限于9/10取代衍生物的文献方法不同，该方法可使用多种官能化的菲。
• Photocyclization of stilbenes. VII. Unusual fluorine atom rearrangement in the photocyclization of 1-fluoro[5]helicenes
  作者：Frank B. Mallory、Clelia W. Mallory

  DOI：10.1021/jo00152a022

  日期：1983.2
• Expeditious synthesis of fluorinated styrylbenzenes and polyaromatic hydrocarbons
  作者：Ashutosh V. Bedekar、Anju R. Chaudhary、M. Shyam Sundar、Murali Rajappa

  DOI：10.1016/j.tetlet.2012.11.022

  日期：2013.1

  A series of fluorinated styrylbenzene derivatives were synthesized by the Mizoroki-Heck reaction using phosphine-free catalytic conditions or by adopting the one-pot Wittig-Heck reaction sequence. The fluorinated styrylbenzenes were converted into polyaromatic hydrocarbons such as phenanthrenes, [4]helicenes, and benzo[ghi]perylene by a modified photocyclization procedure involving I-2-THF condition. (C) 2012 Elsevier Ltd. All rights reserved.