acetyl p-anisoyldiazomethane | 13298-59-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: acetyl p-anisoyldiazomethane
• 英文别名: 2-diazo-1-(4-methoxyphenyl)butane-1,3-dione；Acetyl-(4-methoxy-benzoyl)-diazomethan
• CAS: 13298-59-4
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: QAKVQPXQXXSNOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2Z,4E)-2-azido-4-methyl-5-phenylpenta-2,4-dienoate 、 acetyl p-anisoyldiazomethane 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以85%的产率得到ethyl 6-(1-(4-methoxyphenyl)-1-oxopropan-2-yl)-4-methyl-5-phenylpicolinate
  参考文献：
  名称：

  A Cascade Approach to Pyridines from 2-Azido-2,4-dienoates and α-Diazocarbonyl Compounds

  摘要：

  A one-pot synthesis of substituted pyridines via a cascade reaction of 2-azido-24-dienoates with alpha-diazocarbonyl compounds and triphenylphosphine is reported. The process involves a Staudinger-Meyer reaction, a Wolff rearrangement, ail aza-Wittig reaction, and an electrocyclic ring- closure. The procedure is general and efficient. The substrates are readily available.

  DOI：

  10.1021/jo802159g
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 4-乙酰氨基苯磺酰叠氮 、 sodium hydride 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.03h， 生成 acetyl p-anisoyldiazomethane
  参考文献：
  名称：

  铑（ii）催化的环丙-1-烯-1-基酮的生成及其重排为5-芳基-2-甲硅烷氧基呋喃†

  摘要：

  由Enoldiazoketones形成的供体-受体环丙烯通过一种新的机制进行催化重排，生成5-芳基-2-硅氧基呋喃，该机制涉及将羰基氧亲核加成到铑活化的环丙烯上。

  DOI：

  10.1039/c8cc05623d

文献信息

• Untersuchungen zur Wolff-Umlagerung—II
  作者：K.-P. Zeller、H. Meier、E. Müller

  DOI：10.1016/s0040-4020(01)88926-2

  日期：1972.1

  The migration ability of hydrogen, the methyl, phenyl, p-methoxyphenyl, and p-nitrophenyl groups in the Wolff-rearrangement has been investigated with the aroyl-acyl-diazomethanes 1a-d. The results of the thermal and photochemical (direct and sensitized) reaction are discussed. The insertion of the intermediate aroyl-acylcarbenes 2 in the OH-bond of ethanol yielding 2-ethoxy-1,3-diketones 7 competes

  用芳酰基-酰基-重氮甲烷1a-d研究了氢，甲基，苯基，对甲氧基苯基和对硝基苯基在Wolff重排中的迁移能力。讨论了热和光化学（直接和敏化）反应的结果。中间的插入芳酰基acylcarbenes 2中的乙醇，得到2-乙氧基-1,3-二酮的OH键7米与重排竞速赛2成烯酮（3和4）和β酮酯的形成之后5和6。
• Tandem Synthesis of Benzo[<i>b</i>]carbazoles and Their Photoluminescent Properties
  作者：Yanpeng Xing、Binbin Hu、Qijun Yao、Ping Lu、Yanguang Wang

  DOI：10.1002/chem.201301887

  日期：2013.9.16

  5 H‐Benzo[b]carbazoles were prepared through a tandem reaction between 2‐ethynyl‐N‐triphenylphosphoranylidene anilines and α‐diazoketones through ketenimine intermediates in moderate‐to‐good yields. By using this approach, benzo[b]benzo[5,6]indolo[3,2‐h]carbazoles, fluoreno[9,1‐ab]carbazoles, and fluoreno[9,1‐ab]fluoreno[1′,9′:5,6,7]indolo[3,2‐h]carbazoles were constructed in one pot. Moreover, the

  通过2-乙炔基-N-三苯基磷酰亚苯胺苯胺和α-二氮酮通过酮亚胺中间体的串联反应，以中等至良好的产率制备了5  H-苯并[ b ]咔唑。通过使用这种方法，苯并[ b ]苯并[5,6]吲哚并[3,2- h ]咔唑，芴[9,1- ab ]咔唑和芴[9,1- ab ]氟[1'，9 ′：5,6,7] indolo [3,2- h ]咔唑是在一个锅中制成的。而且，最终产物发出的光在410-521 nm范围内，量子产率高达62％。
• A Tandem Approach to Isoquinolines from 2-Azido-3-arylacrylates and α-Diazocarbonyl Compounds
  作者：Yun-Yun Yang、Wang-Ge Shou、Zheng-Bo Chen、Deng Hong、Yan-Guang Wang

  DOI：10.1021/jo8003259

  日期：2008.5.1

  2-Azido-3-arylacrylates react with α-diazocarbonyl compounds and triphenylphosphine to furnish isoquinolines in 60−92% yields. The tandem process involves a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring closure. The procedure is efficient, rapid, and general, and the substrates are readily available.

  2-氮杂-3-芳基丙烯酸酯与α-重氮羰基化合物和三苯膦反应生成异喹啉，收率60-92％。串联过程涉及Wolff重排，aza-Wittig反应和电环闭合。该过程是有效，快速和通用的，并且基材是容易获得的。
• The Rhodium(II) Acetate-Catalyzed Reaction of Diacyldiazomethanes with Isothiocyanates: Formation of 2-Thioxo-2H-1,3-oxazin-4(3H)-one.
  作者：Hirofumi Nakano、Toshikazu Ibata

  DOI：10.1246/bcsj.66.238

  日期：——

  The rhodium(II) acetate-catalyzed reaction of diacyldiazomethanes such as dibenzoyldiazomethane, acetylaroyldiazomethanes, diacetyldiazomethane, and diazodimedone with isothiocyanates gave 2-thioxo-2H-1,3-oxazin-4(3H)-ones through the [4+2] cycloaddition of isothiocyanates with acylketenes which were derived by the Wolff rearrangement of the diacyldiazomethanes. Migration aptitude of methyl and aryl groups was discussed in the reaction of acetylaroyldiazomethanes.

  在乙酸铑（II）催化下，二苯甲酰二氮杂环丁烷、乙酰甲酰二氮杂环丁烷、二乙酰二氮杂环丁烷和重氮二甲酮等二乙酰二氮杂环丁烷与异硫氰酸盐发生反应，生成 2-硫酮-2H-1、3-恶嗪-4(3H)-酮、通过异硫氰酸酯与酰基烯烃的[4+2]环加成反应，得到 2-硫酮-2H-1, 3-恶嗪-4(3H)-酮。讨论了甲基和芳基在乙酰芳基二氮杂环甲烷反应中的迁移能力。
• Regitz,M., Chemische Berichte, 1966, vol. 99, p. 3128 - 3147
  作者：Regitz,M.

  DOI：——

  日期：——