4-(N-(4-methoxyphenyl)benzamido)-6-phenylpyridin-3-yl benzoate | 1426821-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(N-(4-methoxyphenyl)benzamido)-6-phenylpyridin-3-yl benzoate
• 英文别名: N-allyl-N-(1-phenylvinyl)benzamide
• CAS: 1426821-40-0
• 化学式: C₁₈H₁₇NO
• 分子量: 263.339
• InChiKey: RHHYHCPIRIMLIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(N-(4-methoxyphenyl)benzamido)-6-phenylpyridin-3-yl benzoate 在 zinc trifluoromethanesulfonate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.25h， 生成 4-(N-butylbenzamido)-6-phenylpyridin-3-yl benzoate
  参考文献：
  名称：

  Synthesis of Substituted Pyridines from Cascade [1 + 5] Cycloaddition of Isonitriles to N-Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction

  摘要：

  A novel strategy for de novo synthesis of pyridines featuring an unprecedented a-addition of aldehyde and enamide to isonitrile as a key step is described. Under mild conditions, a cascade reaction involving Zn(OTf)(2)-promoted [1 + 5] cycloaddition of isonitrile with N-formylmethyl-substituted enamide, facile aerobic oxidative aromatization and intermolecular acyl transfer from the pyridinium nitrogen to the 5-hydroxy oxygen, and finally acylation of the 4-amino group by an external acyl chloride efficiently afforded 2-substituted 4-acylamino-5-acyloxypyridines in good to excellent yields.

  DOI：

  10.1021/ja401701x
• 作为产物：
  描述：

  苯乙酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 44.0h， 生成 4-(N-(4-methoxyphenyl)benzamido)-6-phenylpyridin-3-yl benzoate
  参考文献：
  名称：

  光化学生产的氨基环丁烷在热电级联反应中作为掩蔽二烯

  摘要：

  已显示三重态敏化的烯酰胺-烯烃分子内[2 + 2]光环加成反应的环丁烷产物在酸性条件下会发生断裂。通过诱导产生复杂性的热电级联序列，包括原位形成环丁烯，随后进行电环开环，Diels-Alder环加成和随后的内酰胺化，来开发这种不稳定性。激发态光化学和热电级联反应的这种组合允许简单的平面分子迅速转化为富含sp 3的支架。

  DOI：

  10.1021/acs.orglett.9b00211

文献信息

• Rational Design of Triplet Sensitizers for the Transfer of Excited State Photochemistry from UV to Visible
  作者：Luke D. Elliott、Surajit Kayal、Michael W. George、Kevin Booker-Milburn

  DOI：10.1021/jacs.0c05069

  日期：2020.9.2

  Time Dependent Density Functional Theory (TD-DFT) has been used to assist the design and synthesis of a series thioxanthone triplet sensitizers. Calculated energies of the triplet excited state (ET) informed both the type and position of auxochromes placed on the thioxanthone core, enabling fine-tuning of the UV-Vis absorptions and associated triplet energies. The calculated results were highly consistent

  时间相关密度泛函理论 (TD-DFT) 已被用于协助设计和合成一系列噻吨酮三线态敏化剂。计算出的三重激发态 (ET) 能量可以了解位于噻吨酮核心上的辅助色素的类型和位置，从而能够微调 UV-Vis 吸收和相关的三重能量。计算结果在 λmax 和 ET 值的顺序上与实验观察高度一致。然后评估合成的化合物在各种紫外和可见光制备光化学反应中作为三线态敏化剂的功效。这项研究的结果超出了预期；特别是之前在 UV 中敏化的 [2+2] 环加成化学被发现在 455nm（蓝色）发生环加成，相对于输入功率，生产率 (g/h) 增加了 2 到 9 倍。这项研究证明了强大的现代计算方法能够帮助设计成功且高效的三重态敏化光化学反应。
• Manganese(<scp>iii</scp>)-promoted highly stereoselective phosphorylation of acyclic tertiary enamides to synthesize <i>E</i>-selective β-phosphoryl enamides
  作者：Xin-Ming Xu、Wenzhong Li、Qiwei Li、Sen Chen、Xuesi Zhang、Bin Yang、Wei-Li Wang

  DOI：10.1039/d2ob00980c

  日期：——

  A concise manganese(iii)-promoted stereoselective β-phosphorylation of tertiary enamides and diverse H-phosphine oxides was achieved, which proceeds with absolute E-selectivity in high efficiency and is the first case of E-selective β-phosphorylation of tertiary enamides.

  通过简明的锰(iii)促进的立体选择性三级烯酰胺和多样化的H-膦氧的β-磷酸化反应，实现了绝对E选择性高效率的反应，并且是三级烯酰胺E选择性β-磷酸化反应的第一个案例。
• Daisy-Chaining Photo- and Thermal Chemistry: Multistep Continuous Flow Synthesis of Visible-Light-Mediated Photochemistry with a High-Temperature Cascade Reaction
  作者：Luke D. Elliott、Kevin I. Booker-Milburn、Alastair J. J. Lennox

  DOI：10.1021/acs.oprd.1c00187

  日期：2021.8.20

  with an atom economic thermal cascade reaction in a continuous flow process. By moving the photochemistry from ultraviolet (UV) to visible, it is made more energy-efficient and can be conducted with readily available equipment. The application of high-temperature flow chemistry to the thermal cascade step allows for safe and reliable scale-up with short reaction times. Thus, we demonstrate a rare example

  在连续流动过程中，高效的可见光介导的光化学 [2 + 2] 环加成与原子经济的热级联反应相结合。通过将光化学从紫外线 (UV) 转移到可见光，它变得更加节能，并且可以使用现成的设备进行。将高温流动化学应用于热级联步骤可以在较短的反应时间内实现安全可靠的放大。因此，我们展示了一个罕见的光/热菊花链过程的例子，特别是第一个可见光介导的激发态作为一个完全连续的过程 (20 g/h) 的热级联反应。流动化学的合成效用通过在批量条件下不可能的量分离反应性中间体而进一​​步展示。
• A Small-Footprint, High-Capacity Flow Reactor for UV Photochemical Synthesis on the Kilogram Scale
  作者：Luke D. Elliott、Malcolm Berry、Bashir Harji、David Klauber、John Leonard、Kevin I. Booker-Milburn

  DOI：10.1021/acs.oprd.6b00277

  日期：2016.10.21

  The development of a highly compact and powerful reactor for synthetic organic photochemistry is described enabling a 10-fold reduction in reaction times, with up to 30% more power efficiency than previous fluorinated ethylene propylene tube reactors. Two reactions gave over 1 kg of product in 24 h. Two other reactions had productivities of 4 and 8 kg in 24 h. The reactor consists of a succession of quartz tubes connected together in series and arranged axially around a variable power mercury lamp. This compact and relatively simple device can be safely operated in a standard fumehood.