diethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate | 75992-52-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: diethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate
• 英文别名: diethyl (1R,2S,3R,4S)-3,4-diphenylcyclobutane-1,2-dicarboxylate
• CAS: 75992-52-8
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: BULTWXSCCHUVCB-JVSBHGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-<7-(Cinnamoyloxy)heptyl>-6-<6-(cinnamoyloxy)hexyl>-2-pyridone 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 61.0h， 生成 diethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate
  参考文献：
  名称：

  Molecular organization by hydrogen bonding: juxtaposition of remote double bonds for photocyclization in a 2-pyridone dimer

  摘要：

  DOI：

  10.1021/jo00316a027

文献信息

• Photosensitised regioselective [2+2]-cycloaddition of cinnamates and related alkenes
  作者：Santosh K. Pagire、Asik Hossain、Lukas Traub、Sabine Kerres、Oliver Reiser

  DOI：10.1039/c7cc06710k

  日期：——

  An efficient method for the synthesis of substituted cyclobutanes from cinnamates, chalcones, and styrenes has been developed utilizing a visible-light triplet sensitisation mode. This reaction provides a diverse range of substituted cyclobutanes in high yields under mild conditions without the need of external additives. Good regioselectivity is obtained due to strong π–π-stacking of arene moieties

  利用可见光三重态敏化模式已经开发了一种从肉桂酸酯，查耳酮和苯乙烯合成取代环丁烷的有效方法。该反应在温和条件下无需外部添加剂即可高收率地提供各种范围的取代的环丁烷。良好的区域选择性是由于芳烃部分的强烈π-π堆积而获得的，而非对映选择性则取决于芳烃底物的电子效应或邻位取代。木质素天然产物（±）-丹哥酚的形式合成证明了这种转化的效用。
• Using non-covalent interactions to direct regioselective 2+2 photocycloaddition within a macrocyclic cavitand
  作者：Nga Nguyen、Aspen Rae Clements、Mahesh Pattabiraman

  DOI：10.1039/c5nj02376a

  日期：——

  completely from a head-to-head dimer to a head-to-tail dimer. The reactions were also stereoselective in most cases. Stoichiometry experiments were performed to explore relative stabilities of the complexes, which indicate that the ternary complex is more stable than others. Selectivity in the photocycloaddition reaction was also applied retrospectively to deduce intermolecular orientations. Time-dependent

  客体在三元包含复合物中的相对取向受主客体和客客体超分子相互作用的支配。可以使用非共价相互作用来控制大环空分子（γ-环糊精）中包含的两个烯烃之间的2 + 2光环加成反应的选择性。在此手稿中，我们报告了使用非共价相互作用的空泡蛋白介导的烷基肉桂酸酯之间区域选择性的控制。使用这种方法，我们已经表明区域选择性可以完全从头对头二聚体切换到头对尾二聚体。在大多数情况下，反应也是立体选择性的。进行了化学计量学实验以探索配合物的相对稳定性，这表明三元配合物比其他三元配合物更稳定。还追溯应用了光环加成反应中的选择性以推断分子间取向。我们进行的时间依赖性转换研究表明，所观察到的烯烃的反应性代表了复杂介质整体中的分子间取向。通过实验观察和计算研究来定性地了解复杂结构以及弱相互作用的相对强度。以淤浆形式研究了复合物的反应，反应控制的程度表明了类似固态的行为。通过实验观察和计算研究来定性地了解复杂结构以及弱相互作用
• General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible‐Light Catalysis
  作者：Tao Lei、Chao Zhou、Mao‐Yong Huang、Lei‐Min Zhao、Bing Yang、Chen Ye、Hongyan Xiao、Qing‐Yuan Meng、Vaidhyanathan Ramamurthy、Chen‐Ho Tung、Li‐Zhu Wu

  DOI：10.1002/anie.201708559

  日期：2017.11.27

  which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid‐state, molten‐state, or host–guest systems under ultraviolet‐light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular

  [2 + 2]光环加成反应（例如，查耳酮和肉桂酸衍生物的二聚化）是构建环丁烷的独特策略，环丁烷是多种生物活性分子和天然产物的基础。然而，为了克服非刚性烯烃的简便几何异构化的竞争，大多数对上述[2 + 2]的尝试都集中在紫外光照射下的固态，熔融态或主客体系统。我们报告了一种通用且简单的方法来实现这些无环烯烃的分子间[2 + 2]二聚反应，以在可见光下以高度区域和非对映选择性的方式构建环丁烷，这为长期存在的问题提供了有效的解决方案。
• Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides
  作者：Qing-An Wu、Chen-Chao Ren、Feng Chen、Tian-Qi Wang、Yu Zhang、Xue-Fen Liu、Jian-Bin Chen、Shu-Ping Luo

  DOI：10.1016/j.tetlet.2021.153091

  日期：2021.5

  The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the

  查耳酮，肉桂酸酯和肉桂酰胺的[2 + 2]光二聚反应可通过杂配铜（I）配合物有效地催化。反应在温和的反应条件下进行，在可见光照射下以20-72％的收率获得产物。由刚性菲咯啉配体在2,9-位和4,7-位带有取代基的铜基光催化剂在通过能量转移途径的光二聚反应中显示出高活性。
• Donor–acceptor fluorophores as efficient energy transfer photocatalysts for [2 + 2] photodimerization
  作者：Qing-An Wu、Feng Chen、Chen-Chao Ren、Xue-Fen Liu、Hao Chen、Liang-Xuan Xu、Xiao-Cong Yu、Shu-Ping Luo

  DOI：10.1039/c9ob02735a

  日期：——

  Mild [2 + 2] photodimerization of enone substrates was induced by donor-acceptor fluorophores. Enone substrates were activated efficiently for anti-head to head dimerizations with a high yield (up to 83%) and high selectivity. The adjustable excited state potential also allows donor-acceptor fluorophores to be used for isomerization of the above substrates, confirming the potential of donor-acceptor

  供体-受体荧光团诱导了烯酮底物的轻度[2 + 2]光二聚化。高效率（高达83％）和高选择性的Enone底物被有效激活，以防止头对头二聚化。可调的激发态电势还允许将供体-受体荧光团用于上述底物的异构化，证实了供体-受体荧光团作为能量转移光催化剂的潜力。