2-biphenyl-diazoacetophenone | 343254-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-biphenyl-diazoacetophenone
• 英文别名: 2-Diazo-1-[2-(4-phenylphenyl)phenyl]ethanone
• CAS: 343254-62-6
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: LJZSCUNLYBXFEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-biphenyl-diazoacetophenone 在 dirhodium tetraacetate 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以48%的产率得到2-phenyl-9-phenanthrol
  参考文献：
  名称：

  New Fluorogenic Probes for Oxygen and Carbene Transfer:  A Sensitive Assay for Single Bead-Supported Catalysts

  摘要：

  A high-throughput screening assay for atom transfer catalysis has been developed. This assay is based on two probes, developed herein, which generate highly fluorescent products upon carbene or oxygen atom transfer. The emission wavelength of probes 1 and 5 shift significantly (up to 90 nm) upon epoxidation, allowing detection of product at 3% conversion. Probe 7 is not fluorescent, while fluorescence emission by carbene insertion/rearrangement product 8 allows detection at less than 1% conversion. Such sensitivity allows for examination of single-bead reactions in a high throughput array format (1536 wells per plate), and provides a broad detection window ranging from single to high turnover numbers. Thousands of metal complexes are evaluated in a single screening experiment. Preliminary screening of a diverse ligand library with probe 7 in the presence of Rh(II) uncovered new catalysts capable of cyclopropanation and C-H insertion.

  DOI：

  10.1021/ja003786+
• 作为产物：
  描述：

  在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 水 、 乙腈 为溶剂， 以0.96%的产率得到2-biphenyl-diazoacetophenone
  参考文献：
  名称：

  New Fluorogenic Probes for Oxygen and Carbene Transfer:  A Sensitive Assay for Single Bead-Supported Catalysts

  摘要：

  A high-throughput screening assay for atom transfer catalysis has been developed. This assay is based on two probes, developed herein, which generate highly fluorescent products upon carbene or oxygen atom transfer. The emission wavelength of probes 1 and 5 shift significantly (up to 90 nm) upon epoxidation, allowing detection of product at 3% conversion. Probe 7 is not fluorescent, while fluorescence emission by carbene insertion/rearrangement product 8 allows detection at less than 1% conversion. Such sensitivity allows for examination of single-bead reactions in a high throughput array format (1536 wells per plate), and provides a broad detection window ranging from single to high turnover numbers. Thousands of metal complexes are evaluated in a single screening experiment. Preliminary screening of a diverse ligand library with probe 7 in the presence of Rh(II) uncovered new catalysts capable of cyclopropanation and C-H insertion.

  DOI：

  10.1021/ja003786+

文献信息

• Two-Photon Induced Uncaging of a Reactive Intermediate. Multiphoton In Situ Detection of a Potentially Valuable Label for Biological Applications
  作者：Joanne Dyer、Steffen Jockusch、Vojtech Balsanek、Dalibor Sames、Nicholas J. Turro

  DOI：10.1021/jo048053c

  日期：2005.3.1

  [GRAPHICS]Two-photon induced Wolff rearrangement of a terphenyl diazoketone 1 was achieved by using focused laser pulses of 532 nm from a Q-switched Nd:YAG laser. The nonfluorescent terphenyl diazoketone 1 was transformed into a fluorescent ester derivative 4, which can be detected in situ using the focused laser pulses at 532 nm. Laser power dependence studies show that the Wolff rearrangement is induced by two-photon absorption of the terphenyl diazoketone 1, but suggests that more than two photons of 532 nm are involved (a multiphoton process) in excitation of the ester derivative 4.