diethyl 3-oxabicyclo[2.2.2]oct-5-ene-2,2-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: diethyl 3-oxabicyclo[2.2.2]oct-5-ene-2,2-dicarboxylate
• 英文别名: diethyl (1R,4S)-2-oxabicyclo[2.2.2]oct-5-ene-3,3-dicarboxylate
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: CDWKQQJMZZEEGK-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-环己二烯 、 酮基丙二酸二乙酯 在 oxo[2-[[oxophenyl(trifluoromethyl)-λ⁶-sulfanylidene]amino]phenyl]iminophenyl(trifluoromethyl)-λ⁶-sulfane 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以55%的产率得到diethyl 3-oxabicyclo[2.2.2]oct-5-ene-2,2-dicarboxylate
  参考文献：
  名称：

  Functionalized S-perfluorinated sulfoximines: Preparation and evaluation in catalytic processes

  摘要：

  N-substituted S-perfluoroalkylated sulfoximines were synthesized from the NH sulfoximines either by a copper coupling reaction with aryl halides or by a reaction with electrophilic substrates. The procedure allowed the preparation of N,N'-bridged bis sulfoximines and of thioureas. The potential of these new sulfoximines was evaluated in different catalytic processes. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2015.06.020

文献信息

• Chiral CO₂-Synthons via Catalytic Asymmetric Hetero-Diels−Alder Reactions of Ketomalonate and Dienes
  作者：Sulan Yao、Mark Roberson、Frank Reichel、Rita G. Hazell、Karl Anker Jørgensen

  DOI：10.1021/jo990696i

  日期：1999.9.1

  A catalytic enantioselective approach for the formation of chiral CO(2)-synthons is presented. The described methodology is based on the reaction of dienes with diethyl ketomalonate using C(2)-symmetric bisoxazolines as the chiral ligands and copper(II) and zinc(II) as the Lewis acids. For cyclic dienes the reaction proceeds in good yield and with up to 93% ee for 1,3-cyclohexadiene, while for cyclopentadiene

  提出了一种手性CO（2）合成子形成催化对映选择性方法。所描述的方法是基于二烯与酮丁二酸二乙酯的反应，使用C（2）对称的双恶唑啉作为手性配体，铜（II）和锌（II）作为路易斯酸。对于环状二烯，反应以良好的收率进行，并且对于1，3-环己二烯，ee高达93％，而对于环戊二烯，该反应在低温下也进行得很好，但是升高温度会导致逆Diels-Alder反应。已经在不同条件下和针对各种二烯对反应进行了研究，并且发现对于活化的二烯，杂-Diels-Alder和Mukaiyama Aldol产物均被分离。由1的对映选择性杂Diels-Alder反应形成的化合物 3-ketolononate的3-环己二烯已转化为原理上从CO（2）和1,3-环己二烯的[2 + 4]环加成反应形成的CO（2）-合成子，以及有吸引力的光学活性1,4-二取代环己二醇。杂-Diels-Alder加合物的绝对构型是基于1,4-二取代的环己
• A new class of C₁-symmetric monosulfoximine ligands for enantioselective hetero Diels–Alder reactions
  作者：Carsten Bolm、Marinella Verrucci、Oliver Simic、Pier Giorgio Cozzi、Gerhard Raabe、Hiroaki Okamura

  DOI：10.1039/b309556h

  日期：——

  Quinoline-based C1-symmetric sulfoximines have been used as chiral ligands in copper-catalyzed asymmetric hetero Diels-Alder reactions leading to cycloadducts with up to 96% ee.

  在铜催化的不对称杂Diels-Alder反应中，基于喹啉的C1对称亚砜基已被用作手性配体，从而产生具有高达96％ee的环加合物。
• Ethylene-Bridged Bissulfoximines in Copper-Catalyzed Enantioselective Hetero-Diels--Alder Reactions
  作者：Carsten Bolm、Marinella Verrucci、Oliver Simic、Christian P. R. Hackenberger

  DOI：10.1002/adsc.200505104

  日期：2005.10

  Ethylene-bridged bissulfoximines were applied as chiral ligands in copper-catalyzed enantioselective hetero-Diels–Alder reactions. After optimization of the reaction conditions, products with up to 99% ee were obtained.

  在铜催化的对映选择性杂-Diels-Alder反应中，乙烯桥联的双硫代亚砜被用作手性配体。在优化反应条件后，获得具有高达99％ee的产物。
• Functionalized S-perfluorinated sulfoximines: Preparation and evaluation in catalytic processes
  作者：Thanh-Nghi Le、Patrick Diter、Bruce Pégot、Chloée Bournaud、Martial Toffano、Regis Guillot、Giang Vo-Thanh、Yurii Yagupolskii、Emmanuel Magnier

  DOI：10.1016/j.jfluchem.2015.06.020

  日期：2015.11

  N-substituted S-perfluoroalkylated sulfoximines were synthesized from the NH sulfoximines either by a copper coupling reaction with aryl halides or by a reaction with electrophilic substrates. The procedure allowed the preparation of N,N'-bridged bis sulfoximines and of thioureas. The potential of these new sulfoximines was evaluated in different catalytic processes. (C) 2015 Elsevier B.V. All rights reserved.