benzyl 2-(4-cyanophenyl)pyrrolidine-1-carboxylate | 1588517-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: benzyl 2-(4-cyanophenyl)pyrrolidine-1-carboxylate
• 英文别名: Benzyl 2-(4-cyanophenyl)pyrrolidine-1-carboxylate
• CAS: 1588517-10-5
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: LOAHKKCDUMTTNK-UHFFFAOYSA-N

物化性质

• 沸点：
  484.0±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对苯二腈 、 N-carbobenzyloxyproline 在 1-(4-(9H-carbazol-9-yl)phenyl)-3-amino-9H-fluorene-2,4-dicarbonitrile 、 cesium fluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以79%的产率得到benzyl 2-(4-cyanophenyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  3-Amino-fluorene-2,4-dicarbonitriles (AFDCs) as Photocatalysts for the Decarboxylative Arylation of α-Amino Acids and α-Oxy Acids with Arylnitriles

  摘要：

  1-(4-(9H-Carbazol-9-yl)phenyl)-3-amino-9H-fluorene-2,4-dicarbonitrile as a new photocatalyst for the decarboxylative cross-coupling reaction of alpha-amino acids or alpha-oxy carboxylic acids with arylnitriles is described. This light-driven reaction enables a variety of benzylic amines and ethers to be prepared from readily available starting materials under mild conditions.

  DOI：

  10.1021/acs.orglett.9b00443

文献信息

• Decarboxylative Arylation of α-Amino Acids via Photoredox Catalysis: A One-Step Conversion of Biomass to Drug Pharmacophore
  作者：Zhiwei Zuo、David W. C. MacMillan

  DOI：10.1021/ja501621q

  日期：2014.4.9

  The direct decarboxylative arylation of α-amino acids has been achieved via visible light-mediated photoredox catalysis. This method offers rapid entry to prevalent benzylic amine architectures from an abundant biomass, specifically α-amino acid precursors. Significant substrate scope is observed with respect to both the amino acid and arene components.

  α-氨基酸的直接脱羧芳基化是通过可见光介导的光氧化还原催化实现的。这种方法提供了从丰富的生物质，特别是 α-氨基酸前体快速进入流行的苄胺结构的途径。在氨基酸和芳烃组分方面都观察到显着的底物范围。
• Moving Beyond Cyanoarene Thermally Activated Delayed Fluorescence Compounds as Photocatalysts: An Assessment of the Performance of a Pyrimidyl Sulfone Photocatalyst in Comparison to 4CzIPN
  作者：Megan Amy Bryden、Francis Millward、Tomas Matulaitis、Dongyang Chen、Marco Villa、Andrea Fermi、Sultan Cetin、Paola Ceroni、Eli Zysman-Colman

  DOI：10.1021/acs.joc.2c01137

  日期：——

  increased conjugation of pDTCz-DPmS relative to 4CzIPN presents a more intense CT band in the UV–vis absorption spectrum, aiding in the light absorption of this molecule. Prompt and delayed emission lifetimes are observed for pDTCz-DPmS, confirming the TADF nature, both of which are sufficiently long-lived to participate in productive photochemistry. These combined properties make pDTCz-DPmS useful in

  近年来，表现出热激活延迟荧光 (TADF) 的咔唑基二氰基苯 (CDCB) 衍生物已证明自己是出色的光催化剂，尤其是4CzIPN，尽管对有机 TADF 化合物作为 CDCB 组之外的光催化剂的研究受到限制。在此，我们报告了另一种供体-受体 TADF 结构，9,9'-(sulfonylbis(pyrimidine-5,2-diyl))bis(3,6-di-tert - butyl-9H-carbazole)，pDTCz-DPmS，用作光催化剂（PC）。pDTCz-DPmS与4CzIPN的电化学和光物理性质比较在一系列溶剂中，将前者确定为更好的基态还原剂和光还原剂，而两者在基态和激发态下都表现出相似的氧化能力。pDTCz-DPmS相对于4CzIPN增加的共轭在紫外-可见吸收光谱中呈现出更强的 CT 带，有助于该分子的光吸收。观察到pDTCz-DPmS的快速和延迟发射寿命，证实了 TADF 的性
• Multi‐Resonant Thermally Activated Delayed Fluorescent (MR‐TADF) Compounds as Photocatalysts**
  作者：Callum Prentice、James Morrison、Andrew D. Smith、Eli Zysman‐Colman

  DOI：10.1002/chem.202202998

  日期：2023.1.9

  Mes3DiKTa, are shown to be excellent photocatalysts in a range of different reactions, benchmarked against the widely used donor-acceptor TADF photocatalyst, 4CzIPN. Advantages of using these MR-TADF photocatalysts include robust and inexpensive photocatalyst synthesis, lower required photocatalyst loadings and faster reaction rates, while achieving comparable or improved product yields.

  多共振热激活延迟荧光 (MR-TADF) 化合物DiKTa和Mes 3 DiKTa在一系列不同的反应中被证明是出色的光催化剂，以广泛使用的供体-受体 TADF 光催化剂4CzIPN为基准。使用这些 MR-TADF 光催化剂的优势包括稳健且廉价的光催化剂合成、所需的光催化剂负载量更低和反应速率更快，同时实现可比或更高的产品收率。
• 10.1055/a-2338-4243
  作者：Azami, Masaya、Sumimoto, Michinori、Nakamura, Reika、Murafuji, Toshihiro、Kamijo, Shin

  DOI：10.1055/a-2338-4243

  日期：——

  electron-deficient (trifluoromethylsulfonyl)benzene derivatives, as a phenyl precursor, was critical to realizing the present transformation. Moreover, the DFT calculations indicated that the present transformation proceeds via a concerted homolytic aromatic substitution rather than via a stepwise one involving the formation of a cyclohexadienyl radical intermediate.

  使用光激发的 4-苯甲酰吡啶作为氢原子转移，在连接到醚和 N-Boc-胺的杂原子上的非酸性 C(sp 3 )–H 键上实现了一步苯基化（ HAT）催化剂。作为苯基前体的缺电子（三氟甲基磺酰基）苯衍生物的设计对于实现目前的转变至关重要。此外，DFT计算表明，本发明的转化是通过协同均裂芳族取代进行的，而不是通过涉及环己二烯基自由基中间体形成的逐步取代进行的。
• 3-Amino-fluorene-2,4-dicarbonitriles (AFDCs) as Photocatalysts for the Decarboxylative Arylation of α-Amino Acids and α-Oxy Acids with Arylnitriles
  作者：Yiyang Chen、Ping Lu、Yanguang Wang

  DOI：10.1021/acs.orglett.9b00443

  日期：2019.4.5

  1-(4-(9H-Carbazol-9-yl)phenyl)-3-amino-9H-fluorene-2,4-dicarbonitrile as a new photocatalyst for the decarboxylative cross-coupling reaction of alpha-amino acids or alpha-oxy carboxylic acids with arylnitriles is described. This light-driven reaction enables a variety of benzylic amines and ethers to be prepared from readily available starting materials under mild conditions.