1,2-diacetoxy-4-phenylbut-3-ene | 119420-99-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-diacetoxy-4-phenylbut-3-ene
• 英文别名: (E)-4-phenylbut-3-ene-1,2-diyl diacetate；(E)-1,2-diacetoxy-4-phenylbut-3-ene；[(E)-2-acetyloxy-4-phenylbut-3-enyl] acetate
• CAS: 119420-99-4
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: BFXRFNMMZNRBQS-CMDGGOBGSA-N

物化性质

• 沸点：
  362.2±42.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  buta-1,3-dien-1-ylbenzene 、 乙酸酐 在 α,α,α-三联吡啶 、 氧气 、 palladium diacetate 、 溶剂黄146 、 联硼酸频那醇酯 作用下， 以 乙腈 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 以63%的产率得到1,2-diacetoxy-4-phenylbut-3-ene
  参考文献：
  名称：

  B₂pin₂-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O₂ as Oxygen Source and Sole Oxidant

  摘要：

  A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O-2) as both the sole oxidant and oxygen source is developed, which was identified by O-18-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (B(2)pin(2)) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.

  DOI：

  10.1021/acs.orglett.8b01806

文献信息

• Pincer Complex-Catalyzed Redox Coupling of Alkenes with Iodonium Salts via Presumed Palladium(IV) Intermediates
  作者：Juhanes Aydin、Johanna M. Larsson、Nicklas Selander、Kálmán J. Szabó

  DOI：10.1021/ol9010739

  日期：2009.7.2

  Palladium pincer complexes directly catalyze the redox coupling reactions of functionalized alkenes and iodonium salts. The catalytic process, which is suitable for mild catalytic functionalization of allylic acetates and electron-rich alkenes, probably occurs through Pd(IV) intermediates. Due to the strong metal−ligand interactions, the oxidation of phosphine and amine ligands of the pincer complexes

  钯钳配合物直接催化官能化烯烃和碘鎓盐的氧化还原偶联反应。适合于烯丙基乙酸酯和富含电子的烯烃的轻度催化官能化的催化过程，很可能是通过Pd（IV）中间体发生的。由于强的金属-配体相互作用，在所提出的反应中可以避免钳子配合物的膦和胺配体的氧化。
• Highly Regio- and Stereoselective Heck Reaction of Allylic Esters with Arenediazonium Salts: Application to the Synthesis of Kavalactones
  作者：Angélica Venturini Moro、Flávio Sega Pereira Cardoso、Carlos Roque Duarte Correia

  DOI：10.1021/ol901416e

  日期：2009.8.20

  highly efficient palladium-catalyzed Heck reaction of allylic esters with arenediazonium salts is described. The reaction proceeds under mild conditions, with excellent to total regio- and stereochemical control and with retention of the traditional leaving group. Furthermore, the generality of the present methodology is illustrated by the short total synthesis of the natural kavalactones, yangonine,

  描述了烯丙基酯与槟榔重氮盐的高效钯催化的Heck反应。反应在温和的条件下进行，对区域和立体化学的控制极好，并且保留了传统的离去基团。此外，本方法的一般性通过天然的kavalactones，仰光宁，（±）-甲基美替丁素和（±）-二氢甲基美替丁素的短的全合成来说明。
• Morimoto, Takashi; Hirano, Masao; Enokida, Takashi, Journal of the Chemical Society. Perkin transactions II, 1988, p. 1531 - 1536
  作者：Morimoto, Takashi、Hirano, Masao、Enokida, Takashi、Isomoto, Akihito、Hamaguchi, Takayoshi、Zhung, Xumin

  DOI：——

  日期：——
• MORIMOTO, TAKASHI;HIRANO, MASAO;ENOKIDA, TAKASHI;ISOMOTO, AKIHITO;HAMAGUC+, J. CHEM. SOC. PERKIN TRANS. PT 2,(1988) N 8, C. 1531-1535
  作者：MORIMOTO, TAKASHI、HIRANO, MASAO、ENOKIDA, TAKASHI、ISOMOTO, AKIHITO、HAMAGUC+

  DOI：——

  日期：——