1r,2c-diacetyl-3t,4t-diphenyl-cyclobutane | 13518-50-8

• 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: 1r,2c-diacetyl-3t,4t-diphenyl-cyclobutane
• 英文别名: 1,1'-(3,4-diphenylcyclobutane-1,2-diyl)-diethanone；1,1'-(3,4-diphenylcyclobutane-1,2-diyl)diethanone；1r,2c-diacetyl-3t,4t-diphenyl-cyclobutane；1r,2c-Diacetyl-3t,4t-diphenyl-cyclobutan；cis-trans-cis-1.2-Diacetyl-3.4-diphenyl-cyclobutan
• CAS: 13518-50-8
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: ZSCUAUXGICQVOD-JVSBHGNQSA-N

物化性质

• 熔点：
  143 °C
• 沸点：
  432.1±45.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苄叉丙酮 生成 1r,2c-diacetyl-3t,4t-diphenyl-cyclobutane
  参考文献：
  名称：

  Butenandt et al., Justus Liebigs Annalen der Chemie, 1952, vol. 575, p. 123,137

  摘要：

  DOI：

文献信息

• 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。
• Quantum Dots Photocatalyze Intermolecular [2 + 2] Cycloadditions of Aromatic Alkenes Adsorbed to their Surfaces via van der Waals Interactions
  作者：Yishu Jiang、Rafael López-Arteaga、Emily A. Weiss

  DOI：10.1021/jacs.2c00833

  日期：2022.3.9

  mild and selective route to cycloadditions, radical rearrangements, couplings, fragmentations, and isomerizations. Colloidal quantum dots are proven visible-light photosensitizers and structural scaffolds for triplet-initiated reactions of molecules that are functionalized (with carboxylates) to anchor on the QD surface. Here, with the aid of polyaromatic energy shuttles that act as noncovalent adsorption

  三重激发态引发的光化学是一种温和且选择性的环加成、自由基重排、偶联、断裂和异构化途径。胶体量子点被证明是可见光光敏剂和结构支架，用于功能化（用羧酸盐）锚定在 QD 表面的分子的三重引发反应。在这里，借助作为 QD 表面上底物的非共价吸附位点的多环能量穿梭，QD 光催化的分子间 [2 + 2] 环加成的范围扩展到自由扩散的底物（无锚定基团）。QD-穿梭配合物光催化苯扎丙酮、查耳酮及其衍生物的同型和异型分子间 [2 + 2] 光环加成反应，产率高达 94%；3，但具有 2.5 倍的催化剂负载量低、稳定性好、能够通过简单的离心回收催化剂并将其重复用于多个反应循环的优点。实验暗示了两步三重态-三重态能量转移机制，一个能量从 QD 转移到能量穿梭，然后第二个能量从穿梭转移到瞬时吸附的基板。
• Singh, Anil K.; Lalitha, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 935 - 938
  作者：Singh, Anil K.、Lalitha, S.

  DOI：——

  日期：——