5,5-bis(cinnamyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

• 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: 5,5-bis(cinnamyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5,5-dicinnamyl-2,2-dimethyl-1,3-dioxane-4,6-dione；2,2-dimethyl-5,5-bis(3-phenylprop-2-enyl)-1,3-dioxane-4,6-dione
• 化学式: C₂₄H₂₄O₄
• 分子量: 376.452
• InChiKey: FRIXIYVBZBDPGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 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：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 肉桂醇 在 二(氰基苯)二氯化钯 、 三苯基膦 作用下， 以 水 为溶剂， 反应 1.0h， 以77%的产率得到5,5-bis(cinnamyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Activator-free and one-pot C-allylation by simple palladium catalyst in water

  摘要：

  For atom economic and green chemistry concepts, we develop a reaction that involves one-pot and one step to construct the C-C bond without the help of any activating reagents for allylic alcohols in water. The palladium-catalyzed allylation of cyclic 1,3-diones using allylic alcohols directly gave the corresponding allylated products in 8-99% yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.022

文献信息

• Enantiodivergent Synthesis of Tertiary α-Aryl 1-Indanones: Evidence Toward Disparate Mechanisms in the Palladium-Catalyzed Decarboxylative Asymmetric Protonation
  作者：Cian Kingston、Patrick J. Guiry

  DOI：10.1021/acs.joc.7b00303

  日期：2017.4.7

  Herein, we describe a study into the scope and origin of an enantiodivergent effect in the palladium-catalyzed decarboxylative asymmetric protonation. By switching the achiral proton source, both enantiomers of a series of tertiary α-aryl-1-indanones are readily accessed from the corresponding α-aryl-β-keto allyl esters. In this example of dual stereocontrol, enantioselectivities up to 94% (S) and

  在这里，我们描述了对钯催化的脱羧不对称质子化中对映发散作用的范围和起源的研究。通过切换非手性质子源，可以容易地从相应的α-芳基-β-酮烯丙基酯获得一系列叔α-芳基-1-茚满酮的两个对映体。在双重立体控制的这个例子中，分别使用Meldrum的酸和甲酸可实现高达94％（S）和92％（R）的对映选择性。为了合理化这种绝对构型的开关，对脱羧不对称质子化的模棱两可机理进行了研究。提出了与甲酸反应的新型催化循环，并进行了各种实验研究。
• Et3B–Pd-promoted allylation of benzaldehyde with allylic alcohols
  作者：Masanari Kimura、Tatsuya Tomizawa、Yoshikazu Horino、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1016/s0040-4039(00)00429-9

  日期：2000.5

  In the presence of Pd(OAc)(2) (0.05 equiv.) and PPh3 (0.1 equiv.), triethylborane promotes a variety of allyl alcohols to undergo allylation of benzaldehyde to provide homoallyl alcohols in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Palladium Catalyzed Alkylation with Allylic Acetates under Neutral Conditions
  作者：Giuliano Giambastiani、Giovanni Poli

  DOI：10.1021/jo981599c

  日期：1998.12.1
• Activator-free and one-pot C-allylation by simple palladium catalyst in water
  作者：Yi-Jen Shue、Shyh-Chyun Yang

  DOI：10.1016/j.tetlet.2012.01.022

  日期：2012.3

  For atom economic and green chemistry concepts, we develop a reaction that involves one-pot and one step to construct the C-C bond without the help of any activating reagents for allylic alcohols in water. The palladium-catalyzed allylation of cyclic 1,3-diones using allylic alcohols directly gave the corresponding allylated products in 8-99% yields. (C) 2012 Elsevier Ltd. All rights reserved.