1-(2-azido-5-methoxyphenyl)ethanone | 180343-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-azido-5-methoxyphenyl)ethanone
• CAS: 180343-65-1
• 化学式: C₉H₉N₃O₂
• 分子量: 191.189
• InChiKey: RJIHCYFNHKUKAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-azido-5-methoxyphenyl)ethanone 在 copper(l) iodide 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-methyl-5-methoxy-2-(4-methoxyphenyl)-2H-indazole
  参考文献：
  名称：

  A general and efficient approach to 2H-indazoles and 1H-pyrazoles through copper-catalyzed intramolecular N–N bond formation under mild conditions

  摘要：

  一种新型高效的铜催化分子内胺化反应已被开发出来，可以在温和条件下从易于获得的起始材料直接合成各种多取代2H-吲唘和1H-吡唑衍生物。通过采用这种方法，仅用三步就制备出了一种高选择性的雌激素受体β配体。

  DOI：

  10.1039/c1cc13908h
• 作为产物：
  描述：

  1-(2-氨基-5-甲氧基苯基)-乙酮 在 sodium nitrite 、 sodium azide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以81%的产率得到1-(2-azido-5-methoxyphenyl)ethanone
  参考文献：
  名称：

  A general and efficient approach to 2H-indazoles and 1H-pyrazoles through copper-catalyzed intramolecular N–N bond formation under mild conditions

  摘要：

  一种新型高效的铜催化分子内胺化反应已被开发出来，可以在温和条件下从易于获得的起始材料直接合成各种多取代2H-吲唘和1H-吡唑衍生物。通过采用这种方法，仅用三步就制备出了一种高选择性的雌激素受体β配体。

  DOI：

  10.1039/c1cc13908h

文献信息

• Pyrolysis of Aryl Azides. XIII. Conformational Effects on the Ability of Carbonyl as a Neighbouring Group
  作者：LK Dyall、JA Ferguson、TB Jarman

  DOI：10.1071/ch9961197

  日期：——

  Our previous claim, that locking an ortho carbonyl group into a favourable conformation causes very large increases in the rate of thermolysis of aryl azides , has been reexamined. In 8-azido-5-methoxy-1-tetralone the rate advantage over an azide with a rotatable ortho acetyl group is estimated to be only 18-fold. Nevertheless, this factor is large enough to invalidate attempts to explain relative neighbouring group abilities on simple electronic effects alone. The very large rate increases we reported previously for 1-azidoacridin-g(10H)-one and 1-azidoanthracene-9,10-dione are partly due to favourable retention of conjugation in the transition state.

  我们之前的说法是，将一个正交羰基锁定在一个有利的构象中会导致芳基叠氮化合物的热解速率大幅增加，这一说法已经重新审视。在8-叠氮基-5-甲氧基-1-四氢萘中，与一个具有可旋转的正交乙酰基团的叠氮基相比，速率优势仅估计为18倍。然而，这一因素足够大，以至于无法仅通过简单的电子效应来解释相对邻基能力。我们之前报告的1-叠氮基吖啶-9(10H)-酮和1-叠氮基蒽-9,10-二酮的非常大的速率增加部分是由于过渡态中共轭的有利保留。
• Substituent Effects on the Lifetimes and Reactivities of Arylnitrenium Ions Studied by Laser Flash Photolysis and Photothermal Beam Deflection
  作者：Rebecca J. Robbins、David M. Laman、Daniel E. Falvey

  DOI：10.1021/ja961518z

  日期：1996.1.1

  Photolysis of 5-substituted-N-tert-butyl-3-methylanthranilium produces transient N-tert-butyl-(2-acetyl-4-substituted) phenylnitrenium ions. This is confirmed by identification of the stable products, transient absorption experiments, and photothermal beam deflection experiments. Analysis of the stable photoproducts shows that the major decay pathway for these species is addition of nucleophiles to the aromatic ring. The kinetics of the these reactions were examined with the goal of determining how various ring substituents affect arylnitrenium ion stability. Rate constants measured for the 4-phenyl and 4-methoxy derivatives are compared with those from previous work. It is shown that a 4-phenyl group stabilizes the nitrenium ion to approximately the same extent as a 4-methoxy group. Both of these substituents stabilize the arylnitrenium ions considerably more than 4-halogens or a 4-methyl group. Time resolved photothermal beam deflection experiments were applied to the 4-cyano and 4-unsubstituted derivatives, which gave no transient absorption spectra. The latter two compounds are shown to have lifetimes of less than 100 ns.
• A general and efficient approach to 2H-indazoles and 1H-pyrazoles through copper-catalyzed intramolecular N–N bond formation under mild conditions
  作者：Jiantao Hu、Yongfeng Cheng、Yiqing Yang、Yu Rao

  DOI：10.1039/c1cc13908h

  日期：——

  A new efficient copper-catalyzed intramolecular amination reaction has been developed to readily synthesise a wide variety of multi-substituted 2H-indazole and 1H-pyrazole derivatives from easily accessible starting materials under mild conditions. A highly selective ligand for estrogen receptor β was prepared in three steps by employing this method.

  一种新型高效的铜催化分子内胺化反应已被开发出来，可以在温和条件下从易于获得的起始材料直接合成各种多取代2H-吲唘和1H-吡唑衍生物。通过采用这种方法，仅用三步就制备出了一种高选择性的雌激素受体β配体。