pyridin-2-yl(3-p-tolylbicyclo[2.2.1]hept-5-en-2-yl)methanone | 1407183-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pyridin-2-yl(3-p-tolylbicyclo[2.2.1]hept-5-en-2-yl)methanone
• 英文别名: [(1S,2R,3R,4R)-3-(4-methylphenyl)-2-bicyclo[2.2.1]hept-5-enyl]-pyridin-2-ylmethanone
• CAS: 1407183-51-0
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: FEBGSNCSZXRUGE-QFHJOOASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 pyridin-2-yl(3-p-tolylbicyclo[2.2.1]hept-5-en-2-yl)methanone
  参考文献：
  名称：

  一种有效的基于环Di-AMP的人工金属核酶，用于对映选择性Diels-Alder反应

  摘要：

  少量的c-di-AMP和Cu 2+离子环状RNA可以组装成人工金属核酶，该酶​​能够以高达80％ee的催化对映选择性Diels-Alder反应。金属核酶中c-di-AMP的存在不仅实现了手性转移，而且还大大提高了速率。

  DOI：

  10.1002/ejoc.202000652

文献信息

• Asymmetric Catalysis of Diels-Alder Cycloaddition of 2-Alkenoyl Pyridine with Cyclopentadiene by Binaphthol-Titanium Complex
  作者：Li Wang、Ji Zhang、Na Wang、Xin-Bin Yang、Qin Wang、Xiao-Qi Yu

  DOI：10.2174/157017809788681419

  日期：2009.7.1

  Asymmetric Diels-Alder reactions between aza-chalcone and cyclopentadiene (CP) catalyzed by the binaphthol-titanium (BINOL – Ti) in the presence of HMPA (80 mole %) were studied. The products were obtained with up to 87% ees.

  研究了在HMPA（80摩尔％）存在下联萘酚钛（BINOL-Ti）催化的氮杂查尔酮与环戊二烯（CP）之间的不对称Diels-Alder反应。获得的产品具有高达87％的ee。
• N,N′-Dioxide/nickel(<scp>ii</scp>)-catalyzed asymmetric Diels–Alder reaction of cyclopentadiene with 2,3-dioxopyrrolidines and 2-alkenoyl pyridines
  作者：Yan Lu、Yuhang Zhou、Lili Lin、Haifeng Zheng、Kai Fu、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c6cc03346f

  日期：——

  A chiral N,N[prime or minute]-dioxide/Ni(OTf)2 complex-catalyzed asymmetric Diels-Alder reaction of cyclopentadiene with 2,3-dioxopyrrolidines and 2-alkenoyl pyridines has been achieved, leading to the corresponding chiral bridged compounds in up to 97% yield, 95 : 5 dr and 97% ee.

  已实现环戊二烯与2,3-二氧杂吡咯烷和2-链烯基吡啶的手性N，N [原始或分钟]-二氧化物/ Ni（OTf）2络合物催化的不对称Diels-Alder反应，从而导致相应的手性桥联化合物产率高达97％，95：5 dr和97％ee。
• Enantioselective Diels-Alder Reactions with G-Quadruplex DNA-Based Catalysts
  作者：Changhao Wang、Guoqing Jia、Jun Zhou、Yinghao Li、Yan Liu、Shengmei Lu、Can Li

  DOI：10.1002/anie.201204850

  日期：2012.9.10

  DNA in command: An enantioselective Diels–Alder reaction can be achieved using human telomeric G‐quadruplex DNA‐based catalysts. The absolute configuration of the product can be reversed when the conformation of G‐quadruplex DNA is switched from antiparallel to parallel, and both the reaction rate and the enantioselectivity of the Diels–Alder reaction were found to be dependent on the DNA sequence

  掌握的DNA：使用基于人类端粒的G-四链体DNA的催化剂可以实现对映选择性Diels-Alder反应。当G-四链体DNA的构象从反平行转换为平行时，产物的绝对构型可以颠倒，并且发现Diels-Alder反应的反应速率和对映选择性均取决于DNA序列。
• Enantioselective Diels–Alder reactions using a G-triplex DNA-based catalyst
  作者：Xiaowei Xu、Wuxiang Mao、Feng Lin、Jianlin Hu、Zhiyong He、Xiaocheng Weng、Chun-Jiang Wang、Xiang Zhou

  DOI：10.1016/j.catcom.2015.09.012

  日期：2016.1

  found that the G-triplex DNA could be used as an enantioselective catalyst without further addition of ligands in Diels–Alder reactions when coordinated with copper ions, for the first time. The efficiency and selectivity of the catalyst were investigated. The kinetic measurements were made using ultraviolet (UV) light. The stability of the catalyst in aqueous buffer was confirmed by circular dichroism

  在这项研究中，发现当与铜离子配合使用时，在Diels-Alder反应中无需进一步添加配体，就可以将G-三重体DNA用作对映选择性催化剂。研究了催化剂的效率和选择性。动力学测量是使用紫外线（UV）进行的。催化剂在水性缓冲液中的稳定性通过圆二色性（CD）和核磁共振（NMR）光谱确定。
• A Pyrene-Linked Cavity within a β-Barrel Protein Promotes an Asymmetric Diels-Alder Reaction
  作者：Tomoki Himiyama、Naomasa Taniguchi、Shunsuke Kato、Akira Onoda、Takashi Hayashi

  DOI：10.1002/anie.201704524

  日期：2017.10.23

  Selectivity by the barrel-load: A reaction cavity with a tethered polycyclic pyrene moiety, which acts as a platform to provide aromatic interactions, is constructed within the rigid scaffold of the β-barrel nitrobindin protein. An asymmetric Diels–Alder reaction between azachalcone and cyclopentadiene proceeds within the reaction cavity of the pyrene-linked nitrobindin with high stereoselectivity

  通过桶负载的选择性：在β桶硝基硝基丁蛋白的刚性支架内构建了一个带有系留多环pyr部分的反应腔，该平台充当提供芳香相互作用的平台。za唑烷酮与环戊二烯之间的不对称Diels-Alder反应在stereo连接的硝基bindin的反应腔内以高立体选择性进行。