3-tosyloxyflavone | 13800-28-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-tosyloxyflavone
• 英文别名: 2-phenyl-3-(toluene-4-sulfonyloxy)-chromen-4-one；3-(p-Toluolsulfonyloxy)flavenon；3-(p-Toluolsulfonyloxy)-flavon；Tosyloxyflavone；(4-oxo-2-phenylchromen-3-yl) 4-methylbenzenesulfonate
• CAS: 13800-28-7
• 化学式: C₂₂H₁₆O₅S
• 分子量: 392.432
• InChiKey: IWCGDOHZQXIFFP-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C(Solv: ethanol (64-17-5))
• 沸点：
  556.6±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-tosyloxyflavone 在 吡啶 、 氨 作用下， 以 四氢呋喃 为溶剂， 生成 3-N-acetylaminoflavone
  参考文献：
  名称：

  Synthesis of 3-Aminoflavones from 3-Hydroxyflavones via 3-Tosyloxy- or 3-Mesyloxyflavones

  摘要：

  三甲磺酸基氧黄酮或三甲砜酸基氧黄酮与氨或伯胺反应，以高产率生成相应的3-氨基黄酮。通过此方法，从芸香苷高效制备了3-氨基芦丁。

  DOI：

  10.1246/cl.2006.128
• 作为产物：
  描述：

  2'-羟基查耳酮 在 双氧水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 3-tosyloxyflavone
  参考文献：
  名称：

  The rearrangement of tosylated flavones to 1′-(alkylamino)aurones with primary amines

  摘要：

  A rearrangement of 3-tosylflavone to the corresponding 1'-(alkylamino)aurone proceeds under mild conditions in the presence of primary amines in high yields. The reaction is applicable to different substituted 3-tosylflavones and alkyl amines and the respective aurones were isolated as a mixture of E/Z isomers. Further conversion of 1'-(methylamino)aurone to the corresponding thionated compound was performed by reaction with Lawesson's reagent and only the E isomer was obtained. This observation can be explained by the weaker exocyclic double bond, which facilitates rotation and the formation of the thermodynamically preferred E form. The characterization, preliminary biological investigations of the synthesized compounds and lipophilicity studies are discussed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.062

文献信息

• Chroman‐4‐one‐Based Amino Bidentate Ligand: An Efficient Ligand for Suzuki‐Miyaura and Mizoroki‐Heck Coupling Reactions in Aqueous Medium
  作者：Danish Khan、Iram Parveen

  DOI：10.1002/ejoc.202100866

  日期：2021.9.21

  A new family of phosphine-free, air and moisture stable ligand are developed for coupling reaction. The synthesised ligand efficiently catalyzed the coupling reaction with PdCl2. The main advantage of the developed protocol is the tolerance of wide substrate including sterically hindered substrates, low ligand loading and short reaction time with good-to-excellent yield.

  为偶联反应开发了一个新的不含膦、空气和水分稳定的配体系列。合成的配体有效地催化了与 PdCl 2的偶联反应。所开发的协议的主要优点是对宽底物的耐受性，包括空间位阻底物、低配体负载和短反应时间，产率良好。
• PATONAY T.; RAKOSI M.; LITKEI G.; BOGNAR R., LIEBIGS ANN. CHEM., 1979, NO 2, 162-173
  作者：PATONAY T.、 RAKOSI M.、 LITKEI G.、 BOGNAR R.

  DOI：——

  日期：——
• Synthesis of 3-Aminoflavones from 3-Hydroxyflavones via 3-Tosyloxy- or 3-Mesyloxyflavones
  作者：Atsushi Takechi、Hirosato Takikawa、Hideyoshi Miyake、Mitsuru Sasaki

  DOI：10.1246/cl.2006.128

  日期：2006.1

  Reaction of 3-tosyloxy- or 3-mesyloxyflavones with ammonia or primary amines proceeded to give the corresponding 3-aminoflavones in high yields. 3-Aminoluteorin was efficiently prepared from rutin using this method.

  三甲磺酸基氧黄酮或三甲砜酸基氧黄酮与氨或伯胺反应，以高产率生成相应的3-氨基黄酮。通过此方法，从芸香苷高效制备了3-氨基芦丁。
• The rearrangement of tosylated flavones to 1′-(alkylamino)aurones with primary amines
  作者：Wolfgang Kandioller、Mario Kubanik、Anna K. Bytzek、Michael A. Jakupec、Alexander Roller、Bernhard K. Keppler、Christian G. Hartinger

  DOI：10.1016/j.tet.2015.09.062

  日期：2015.11

  A rearrangement of 3-tosylflavone to the corresponding 1'-(alkylamino)aurone proceeds under mild conditions in the presence of primary amines in high yields. The reaction is applicable to different substituted 3-tosylflavones and alkyl amines and the respective aurones were isolated as a mixture of E/Z isomers. Further conversion of 1'-(methylamino)aurone to the corresponding thionated compound was performed by reaction with Lawesson's reagent and only the E isomer was obtained. This observation can be explained by the weaker exocyclic double bond, which facilitates rotation and the formation of the thermodynamically preferred E form. The characterization, preliminary biological investigations of the synthesized compounds and lipophilicity studies are discussed. (C) 2015 Elsevier Ltd. All rights reserved.