Ethyl 3-(2-oxo-1,3-oxazolidine-3-carbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

• 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-(2-oxo-1,3-oxazolidine-3-carbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: BEEDOFDKBAUYRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  环戊二烯 、 3-[(E)-3-(ethoxycarbonyl)propenoyl]-2-oxazolidinone 在 Pd(SbF₆)2-[(R)-BINAP] complex 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以96%的产率得到Ethyl 3-(2-oxo-1,3-oxazolidine-3-carbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate
  参考文献：
  名称：

  Counterions of BINAP−Pt(II) and −Pd(II) Complexes:  Novel Catalysts for Highly Enantioselective Diels−Alder Reaction

  摘要：

  Platinum and palladium chiral bisphosphine complexes and their counterion effects in asymmetric Diels-Alder reactions have been investigated. The reaction of cyclopentadiene and various bidentate dienophiles in the presence of a catalytic amount of Pt(ll)- or Pd(ll)-BINAP complex proceeds with excellent endo/exo selectivity as well as endo enantioselectivity (up to 99% ee).

  DOI：

  10.1021/ol990346i

文献信息

• Reuse of chiral cationic Pd–phosphinooxazolidine catalysts in ionic liquids: highly efficient catalytic asymmetric Diels–Alder reactions
  作者：Kouichi Takahashi、Hiroto Nakano、Reiko Fujita

  DOI：10.1039/b611228e

  日期：——

  Chiral cationic palladium-phosphinooxazolidine catalysts in ionic liquid afforded excellent enantioselectivity in Diels-Alder reactions and the catalyst was easily recycled eight times without any significant decrease in chemical yields or enantioselectivity (89-99%, 88-99% ee).

  离子液体中的手性阳离子钯-膦基恶唑烷催化剂在Diels-Alder反应中具有出色的对映选择性，该催化剂易于回收八次，而化学收率或对映选择性没有明显降低（89-99％，88-99％ee）。
• A novel and efficient chiral palladium–phosphinooxazolidine catalyst for the enantioselective Diels–Alder reactionElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b2/b201625g/
  作者：Hiroto Nakano、Yuko Okuyama、Yuichiro Suzuki、Reiko Fujita、Chizuko Kabuto

  DOI：10.1039/b201625g

  日期：2002.5.9

  An efficient ruthenium-catalyzed transfer dehydrogenation of amines to imines was acheived under mild conditions using 2,6-dimethoxy benzoquinone (2) or cat. 2/MnO2 as oxidant.

  在温和的条件下，使用2,6-二甲氧基苯醌（2）或催化剂，可实现有效的钌催化的胺向亚胺的转移脱氢。2 / MnO2作氧化剂。
• 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.
• US7262299B2
  申请人：——

  公开号：US7262299B2

  公开（公告）日：2007-08-28
• Counterions of BINAP−Pt(II) and −Pd(II) Complexes:  Novel Catalysts for Highly Enantioselective Diels−Alder Reaction
  作者：Arun K. Ghosh、Hideho Matsuda

  DOI：10.1021/ol990346i

  日期：1999.12.1

  Platinum and palladium chiral bisphosphine complexes and their counterion effects in asymmetric Diels-Alder reactions have been investigated. The reaction of cyclopentadiene and various bidentate dienophiles in the presence of a catalytic amount of Pt(ll)- or Pd(ll)-BINAP complex proceeds with excellent endo/exo selectivity as well as endo enantioselectivity (up to 99% ee).