8-(trifluoromethyl)-6H-benzo[c]chromen-6-one | 1238196-86-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-(trifluoromethyl)-6H-benzo[c]chromen-6-one
• 英文别名: 8-(Trifluoromethyl)-6H-dibenzo[b,d]pyran-6-one；8-(trifluoromethyl)benzo[c]chromen-6-one
• CAS: 1238196-86-5
• 化学式: C₁₄H₇F₃O₂
• 分子量: 264.204
• InChiKey: KMGURWCOTUFSFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4'-(trifluoromethyl)-1,1'-biphenyl-2carboxylic acid 在 过氧乙酸 、 六氟异丙醇 、 4-碘甲苯 、 溶剂黄146 作用下， 反应 24.0h， 以67%的产率得到8-(trifluoromethyl)-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  轻度ArI催化的C（sp2）？H或C（sp3）？H功能化/ C ？O的形成：一个有趣的催化剂控制的选择性开关

  摘要：

  C（SP A串联2） H和C（SP 3） ħ官能/ C 由碘催化O键形成原位产生（III）的试剂已经被开发出来。该方法在温和条件下显示范围广，并且显示出前所未有的选择性曲线，可以根据所用催化剂进行切换。

  DOI：

  10.1002/anie.201407011

文献信息

• Novel and Efficient One-Step Parallel Synthesis of Dibenzopyranones via Suzuki−Miyaura Cross Coupling
  作者：Kodumuru Vishnumurthy、Alexandros Makriyannis

  DOI：10.1021/cc100068a

  日期：2010.9.13

  Microwave-promoted novel and efficient one-step parallel synthesis of dibenzopyranones and heterocyclic analogues from bromo arylcarboxylates and o-hydroxyarylboronic acids via Suzuki−Miyaura cross coupling reaction is described. Spontaneous lactonization gave dibenzopyranones and heterocyclic analogues bearing electron-donating and -withdrawing groups on both aromatic rings in good to excellent yields

  描述了通过微波促进的新型有效的一步苯并吡喃酮和杂环类似物通过Suzuki-Miyaura交叉偶联反应从溴代芳基羧酸盐和邻-羟基芳基硼酸平行合成的方法。自发的内酯化以良好或优异的产率得到了在两个芳族环上带有给电子和吸电子基团的二苯并吡喃酮和杂环类似物。
• Synthesis of Dibenzopyranones through Palladium-Catalyzed Directed C-H Activation/Carbonylation of 2-Arylphenols
  作者：Shuang Luo、Fei-Xian Luo、Xi-Sha Zhang、Zhang-Jie Shi

  DOI：10.1002/anie.201304295

  日期：2013.9.27

  Dibenzopyranones were synthesized by a palladium‐catalyzed phenol‐directed C–H activation/carbonylation of 2‐phenylphenol derivatives in the presence of CO. Pd(OAc)2 was used as a catalyst and Cu(OAc)2 as a catalytic oxidant in the presence of air.

  二苯并吡喃酮是在CO存在下，通过钯催化的苯酚引导的2-苯基苯酚衍生物的C–H活化/羰基化反应合成的。Pd（OAc）2作为催化剂，Cu（OAc）2作为催化剂氧化剂。空气的存在。
• Ruthenium-Catalyzed Carbonylative C–H Cyclization of 2-Arylphenols: A Novel Synthetic Route to 6<i>H</i>-Dibenzo[<i>b,d</i>]pyran-6-ones
  作者：Kiyofumi Inamoto、Jun Kadokawa、Yoshinori Kondo

  DOI：10.1021/ol401734m

  日期：2013.8.2

  Catalytic carbonylative C-H cyclization of 2-arylphenols can be achieved in the presence of a ruthenium-based catalytic system. The process proceeds efficiently under balloon pressure of CO and produces variously substituted 6H-dibenzo[b,d]pyran-6-one compounds, typically in good to high yields. Functional groups such as the alkoxycarbonyl and acetyl groups as well as halogen atoms (F, Cl, and Br) are well tolerated during the reaction.
• Mild ArI-Catalyzed C(sp²)H or C(sp³)H Functionalization/CO Formation: An Intriguing Catalyst-Controlled Selectivity Switch
  作者：Xueqiang Wang、Joan Gallardo-Donaire、Ruben Martin

  DOI：10.1002/anie.201407011

  日期：2014.10.6

  A tandem C(sp2)H and C(sp3)H functionalization/CO bond formation catalyzed by iodine(III) reagents generated in situ has been developed. The method shows wide scope under mild conditions and exhibits an unprecedented selectivity profile that can be switched depending on the catalyst employed.

  C（SP A串联2） H和C（SP 3） ħ官能/ C 由碘催化O键形成原位产生（III）的试剂已经被开发出来。该方法在温和条件下显示范围广，并且显示出前所未有的选择性曲线，可以根据所用催化剂进行切换。