diethyl 2-(1-((benzyloxy)carbonyl)pyrrolidin-2-yl)succinate | 88001-45-0

• 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: diethyl 2-(1-((benzyloxy)carbonyl)pyrrolidin-2-yl)succinate
• 英文别名: diethyl 2-(1-phenylmethoxycarbonylpyrrolidin-2-yl)butanedioate
• CAS: 88001-45-0
• 化学式: C₂₀H₂₇NO₆
• 分子量: 377.437
• InChiKey: WMWFDNMJEMEEPY-UHFFFAOYSA-N

物化性质

• 沸点：
  483.7±25.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-(1-((benzyloxy)carbonyl)pyrrolidin-2-yl)succinate 在 W-2 Raney Ni lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、1.47 MPa 条件下， 反应 21.0h， 生成 [(1S,8R)-2,3,5,6,7,8-六氢-1H-吡咯里嗪-1-基]甲醇
  参考文献：
  名称：

  Electroorganic chemistry. 79. Efficient synthesis of pyrrolizidine and indolizidine alkaloids utilizing anodically prepared .alpha.-methyoxy carbamates as key intermediates

  摘要：

  DOI：

  10.1021/jo00176a016
• 作为产物：
  描述：

  1-Cbz-吡咯烷 在 盐酸 、 sodium hydroxide 、 硫酸 、 水 、 sodium 、 四氯化钛 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 39.5h， 生成 diethyl 2-(1-((benzyloxy)carbonyl)pyrrolidin-2-yl)succinate
  参考文献：
  名称：

  Electroorganic chemistry. 79. Efficient synthesis of pyrrolizidine and indolizidine alkaloids utilizing anodically prepared .alpha.-methyoxy carbamates as key intermediates

  摘要：

  DOI：

  10.1021/jo00176a016

文献信息

• 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。
• Lessons learnt in photocatalysis – the influence of solvent polarity and the photostability of the photocatalyst
  作者：Megan Amy Bryden、Francis Millward、Oliver S. Lee、Lauren Cork、Malte C. Gather、Andreas Steffen、Eli Zysman-Colman

  DOI：10.1039/d3sc06499a

  日期：——

  properties of photocatalysts as a function of solvent based on a study of eight PCs in four solvents of varying polarity. A range of photocatalytic electron and energy transfer reactions were investigated using a subset of the PCs. For the photoredox reactions, the yields are not correlated with solvent polarity. Instead, when the PC could promote the formation of the target product, we observed photodegradation

  在此，我们通过对四种不同极性溶剂中的八种 PC 的研究表明，光催化剂的三线态能量和氧化还原性质随着溶剂的变化而存在显着变化。使用 PC 的子集研究了一系列光催化电子和能量转移反应。对于光氧化还原反应，产率与溶剂极性无关。相反，当 PC 可以促进目标产物的形成时，我们观察到所有 PC 在所有溶剂中都会发生光降解，这是文献中很少研究的。因此，这使得很难确定母体PC和/或光降解产物是否负责光化学，或者实际上光降解是否实际上对反应产率有害。相反，PCs被发现对于能量转移反应具有光稳定性；然而，产率与 PC 的三重态能量无关，这凸显出三重态能量本身并不是区分 PC 在光诱导能量转移过程中性能的合适描述符。
• Mechanophotocatalysis: A Generalizable Approach to Solvent‐minimized Photocatalytic Reactions for Organic Synthesis
  作者：Francis Millward、Eli Zysman‐Colman

  DOI：10.1002/anie.202316169

  日期：2024.3.22

  Via the synergistic union with mechanochemistry, four archetypal photocatalysis reactions have been realized under solvent-free or solvent-minimized conditions. The mechanophotocatalytic versions feature competitive or superior efficiencies to the solution-state reactions, while also showcasing an enhanced tolerance to aerobic conditions.

  通过与机械化学的协同结合，在无溶剂或溶剂最小化条件下实现了四种典型的光催化反应。机械光催化版本具有与溶液态反应相比具有竞争性或优越的效率，同时还表现出对有氧条件的增强的耐受性。
• A Toolbox Approach To Construct Broadly Applicable Metal-Free Catalysts for Photoredox Chemistry: Deliberate Tuning of Redox Potentials and Importance of Halogens in Donor–Acceptor Cyanoarenes
  作者：Elisabeth Speckmeier、Tillmann G. Fischer、Kirsten Zeitler

  DOI：10.1021/jacs.8b08933

  日期：2018.11.14

  The targeted choice of specific photocatalysts has been shown to play a critical role for the successful realization of challenging photoredox catalytic transformations. Herein, we demonstrate the successful implementation of a rational design strategy for a series of deliberate structural manipulations of cyanoarene-based, purely organic donor-acceptor photocatalysts, using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a starting point. Systematic modifications of both the donor substituents as well as the acceptors' molecular core allowed us to identify strongly oxidizing as well as strongly reducing catalysts (e.g., for an unprecedented detriflation of unactivated naphthol triflate), which additionally offer remarkably balanced redox potentials with predictable trends. Especially halogen arene core substitutions are instrumental for our targeted alterations of the catalysts' redox properties. Based on their preeminent electrochemical and photophysical characteristics, all novel, purely organic photoredox catalysts were evaluated in three challenging, mechanistically distinct classes of benchmark reactions (either requiring balanced, highly oxidizing or strongly reducing properties) to demonstrate their enormous potential as customizable photocatalysts, that outperform and complement prevailing typical best photocatalysts.