ethyl 3,4-dimethyl-6-(2-oxooxazolidine-3-carbonyl)cyclohex-3-enecarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: ethyl 3,4-dimethyl-6-(2-oxooxazolidine-3-carbonyl)cyclohex-3-enecarboxylate
• 英文别名: ethyl (1R,6R)-3,4-dimethyl-6-(2-oxo-1,3-oxazolidine-3-carbonyl)cyclohex-3-ene-1-carboxylate
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: LXFGFMGLCBMGNY-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-[(E)-3-(ethoxycarbonyl)propenoyl]-2-oxazolidinone 、 2,3-二甲基-1,3-丁二烯 在 silver hexafluoroantimonate 、 N-trifluoroethyl-bis(tert-butanesulfinyl)imidoamidine 、 copper dichloride 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 ethyl 3,4-dimethyl-6-(2-oxooxazolidine-3-carbonyl)cyclohex-3-enecarboxylate 、 ethyl 3,4-dimethyl-6-(2-oxooxazolidine-3-carbonyl)cyclohex-3-enecarboxylate
  参考文献：
  名称：

  双（亚磺酰基）亚氨基am配体在铜催化的Diels-Alder反应中的制备及应用。

  摘要：

  描述了基于亚磺酰基亚胺官能团的新型配体的设计和制备。特别地，报道了双（亚磺酰基）亚氨基am（siam）配体的有效和模块化的合成。合成序列的多功能性通过制备各种类似物来证明，以探索关于配体骨架的取代对催化活性的影响。siam配体在不对称催化中的效用在Cu（II）催化的Diels-Alder反应中得到了证明，其中报道了一系列N-酰基氧杂唑烷酮二烯亲和体和二烯底物组合的高度对映和非对映选择性反应。特别值得注意的是这些不对称催化剂对涉及具有挑战性和相对不反应性的无环二烯底物的反应的效率。最后，

  DOI：

  10.1021/jo020524c

文献信息

• The Preparation and Utility of Bis(sulfinyl)imidoamidine Ligands for the Copper-Catalyzed Diels−Alder Reaction
  作者：Timothy D. Owens、Andrew J. Souers、Jonathan A. Ellman

  DOI：10.1021/jo020524c

  日期：2003.1.1

  The design and preparation of a novel class of ligands based on the sulfinyl imine functionality is described. In particular, an efficient and modular synthesis of bis(sulfinyl)imidoamidine (siam) ligands is reported. The versatility of the synthetic sequence is demonstrated by the preparation of various analogues to explore the effect of substitution about the ligand framework on catalytic activity

  描述了基于亚磺酰基亚胺官能团的新型配体的设计和制备。特别地，报道了双（亚磺酰基）亚氨基am（siam）配体的有效和模块化的合成。合成序列的多功能性通过制备各种类似物来证明，以探索关于配体骨架的取代对催化活性的影响。siam配体在不对称催化中的效用在Cu（II）催化的Diels-Alder反应中得到了证明，其中报道了一系列N-酰基氧杂唑烷酮二烯亲和体和二烯底物组合的高度对映和非对映选择性反应。特别值得注意的是这些不对称催化剂对涉及具有挑战性和相对不反应性的无环二烯底物的反应的效率。最后，
• Chiral Phosphinooxazolidine Ligands for Palladium- and Platinum-Catalyzed Asymmetric Diels−Alder Reactions
  作者：Hiroto Nakano、Kouichi Takahashi、Yuko Okuyama、Chieko Senoo、Natsumi Tsugawa、Yuichiro Suzuki、Reiko Fujita、Kazuo Sasaki、Chizuko Kabuto

  DOI：10.1021/jo049375j

  日期：2004.10.1

  Cationic palladium (Pd)- and platinum (Pt)-phosphinooxazolidine catalysts 13a-c, 15a-d, 17a-c, and 19a-c were prepared from phosphinooxazolidine ligands 1-3, MCl2 (M = Pd and Pt), and counterions, and the activities of the catalysts in the asymmetric Diels-Alder (DA) reactions of cyclic or acyclic dienes with imide dienophiles were investigated. These catalysts demonstrated high levels of catalytic activity. The cationic Pd-POZ complex 13c provided particularly excellent enantioselectivity (98% ee) in the DA reactions of cyclopentadiene with acryloyl-, crotonyl-, and fumaroyl-1,3-oxazolidin-2-ones (20a-c).
• Rational Design of Highly Effective Asymmetric Diels−Alder Catalysts Bearing 4,4′-Sulfonamidomethyl Groups
  作者：Akira Sakakura、Rei Kondo、Yuki Matsumura、Matsujiro Akakura、Kazuaki Ishihara

  DOI：10.1021/ja906098b

  日期：2009.12.16

  The rational design of bis(oxazoline)-copper(II) catalysts based on postulated intramolecular secondary n-cation interaction for the highly enantioselective Diels-Alder reaction is presented. A theoretical calculation suggested that the n electrons of the 4,4'-sulfonamidomethyl groups successfully interact with the Cu(II) cation and that the counteranions with protons of sulfonamido groups. These secondary interactions might be essential for the high catalytic activity, the broad range of substrates, and the high level of induction of the enantioselectivity.