2,2-dimethyl-4,6-dioxo-5,5-di(3-phenyl-2-propenyl)-1,3-dioxane | 121740-85-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,2-dimethyl-4,6-dioxo-5,5-di(3-phenyl-2-propenyl)-1,3-dioxane
• 英文别名: 5,5-bis(trans-cinnamyl)-2,2-dimethyl-1,3-dioxane-4,6-dione；5,5-dicinnamyl-2,2-dimethyl-1,3-dioxane-4,6-dione；5,5-dicinnamyl-2,2-dimethyl-1,3-dioxan-4,6-dione；2,2-dimethyl-5,5-bis[(E)-3-phenylprop-2-enyl]-1,3-dioxane-4,6-dione
• CAS: 121740-85-0
• 化学式: C₂₄H₂₄O₄
• 分子量: 376.452
• InChiKey: FRIXIYVBZBDPGI-KAVGSWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  丙二酸环(亚)异丙酯 、 3-苯基丙-2-烯-1-醇 在 四(三苯基膦)钯 溶剂黄146 作用下， 反应 0.5h， 以71%的产率得到2,2-dimethyl-4,6-dioxo-5,5-di(3-phenyl-2-propenyl)-1,3-dioxane
  参考文献：
  名称：

  在纯净条件下，在钯/羧酸催化剂存在下，碳亲核试剂将烯丙醇直接烯丙基取代

  摘要：

  在纯条件下（无有机溶剂或无水作为溶剂），在Pd（PPh 3）4 /羧酸联合催化体系存在下，烯丙醇与碳原核亲核试剂的反应使原核亲核试剂直接烯丙基化，得到相应的烯丙基化产品，收率很高。

  DOI：

  10.1016/j.tetlet.2004.02.094

文献信息

• Practical Pd/C-Mediated Allylic Substitution in Water
  作者：François-Xavier Felpin、Yannick Landais

  DOI：10.1021/jo050952t

  日期：2005.8.1

  Pd/C-mediated allylic substitution in water is described as an interesting alternative to classical homogeneous conditions. The reaction applied to allylic acetates showed a wide range of compatibility with various nitrogen, sulfur, oxygen, and carbon nucleophiles. Notably, the method features inexpensive reagents and a nontoxic solvent. Moreover, measurement of the palladium content in water by ICP-MS

  水中Pd / C介导的烯丙基取代被描述为经典均质条件的一种有趣替代方法。应用于烯丙基乙酸酯的反应显示出与各种氮，硫，氧和碳亲核试剂的广泛相容性。值得注意的是，该方法具有廉价的试剂和无毒的溶剂的特点。此外，通过ICP-MS测量水中的钯含量显示出低的钯污染（4 ppm），与均匀条件相比，该方法对环境更安全。还公开了Pd / C介导的烯丙基取代的第一个不对称实例。
• Green and Scalable Palladium-on-Carbon-Catalyzed Tsuji-Trost Coupling Reaction Using an Efficient and Continuous Flow System
  作者：Clément Cazorla、Muriel Billamboz、Hervé Bricout、Eric Monflier、Christophe Len

  DOI：10.1002/ejoc.201601311

  日期：2017.2.10

  continuous flow Tsuji-Trost coupling reaction between allylic compounds and various nucleophiles was successfully achieved within only ca. 40 s during the single-pass through a cartridge filled with palladium on carbon (Pd/C). Two methods have been designed using the H-cube ThalesNano technology and enable the efficient production of add-valued compounds in the gramm-scale with high productivity. Under

  烯丙基化合物和各种亲核试剂之间的第一个连续流动的Tsuji-Trost偶联反应仅在大约20分钟内成功实现。单程通过充满钯碳 (Pd/C) 的墨盒需要 40 秒。使用 H-cube ThalesNano 技术设计了两种方法，能够以高生产率高效生产克级增值化合物。在优化条件下，筒式催化剂可连续使用 60 分钟，反应性不会降低。大量的底物和亲核试剂成功地提交给标准方法，具有良好的收率和生产力。
• Palladium catalyzed c-allylation of highly acidic carbo and heterocyclic β-dicarbonyl compounds
  作者：M. Prat、M. Moreno-Mañas、J. Ribas

  DOI：10.1016/s0040-4020(01)86091-9

  日期：1988.1

  Highly acidic carbo and heterocyclic β-dicarbonyl compounds such as barbituric acid, 3,5-dimethyl-2-1,2,6-thiadiazine 1,1-dioxide, cyclohexane-1,3-dione, tetronic acids, Meldrum acid and 1,2-diphenylpyrazolidine-3,5-dione are efficiently C-allylated with primary and secondary allylating agents under palladium catalysis.

  高酸性碳和杂环β-二羰基化合物，例如巴比妥酸，3,5-二甲基-2 -1,2,6-噻二嗪1,1-二氧化物，环己烷-1,3-二酮，四氢代酸，Meldrum酸和1在钯催化下，用伯和仲烯丙基化剂有效地将2--二苯基吡唑烷-3,5-二酮进行C-烯丙基化。
• Palladium-Catalyzed, Carboxylic Acid-Assisted Allylic Substitution of Carbon Nucleophiles with Allyl Alcohols as Allylating Agents in Water
  作者：Kei Manabe、Shū Kobayashi

  DOI：10.1021/ol035126q

  日期：2003.9.1

  [structure: see text] Allylic substitution of allyl alcohols in water as a suspension medium has been realized using a combination of tetrakis(triphenylphosphine)palladium and a carboxylic acid such as 1-adamantanecarboxylic acid. Various substrates turned out to be applicable to this catalytic system.

  [结构：见正文]使用四（三苯基膦）钯和羧酸如1-金刚烷羧酸的组合已经实现了作为悬浮介质的水中烯丙醇的烯丙基取代。事实证明，各种底物可适用于该催化体系。
• Et3B-promoted, Pd(0)-catalyzed allylation of active methylene compounds with allylic alcohols
  作者：Yoshinao Tamaru、Yoshikazu Horino、Misato Araki、Shuji Tanaka、Masanari Kimura

  DOI：10.1016/s0040-4039(00)00934-5

  日期：2000.7

  Triethylborane promotes the Pd(0)-catalyzed allylation of active methylene compounds (Meldrum's acid and malonates) with a variety of allylic alcohols. The reaction proceeds smoothly at room temperature and provides the allylation products in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.