(+)-3-benzoyl-2-oxabicyclo[2.2.2]oct-5-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-3-benzoyl-2-oxabicyclo[2.2.2]oct-5-ene
• 英文别名: 2-Oxabicyclo[2.2.2]oct-5-en-3-yl(phenyl)methanone；2-oxabicyclo[2.2.2]oct-5-en-3-yl(phenyl)methanone
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: PGNWZISISIOBOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯基丙醇水合物 、 1,3-环己二烯 在 3 Angstroem MS 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以74%的产率得到(+)-3-benzoyl-2-oxabicyclo[2.2.2]oct-5-ene
  参考文献：
  名称：

  Asymmetric Hetero Diels−Alder Reaction Catalyzed by Chiral Cationic Palladium(II) and Platinum(II) Complexes

  摘要：

  The hetero Diels-Alder reaction of nonactivated conjugated dienes 1 with arylglyoxals 2 and glyoxylate esters 7 proceeded enantioselectively in the presence of a catalytic amount of cationic chiral BINAP-palladium or -platinum complexes and 3 Angstrom molecular sieves (MS3A). The addition of MS3A effectively improved the enantioselectivity of the reaction. Excellent ee's were obtained from the reactions of 2,3-dimethyl-1,3-butadiene (1a) and 1,3-cyclohexadiene (1d) with dienophiles 2 and 7. The square-planar structure of [Pd(S-BINAP)(PhCN)(2)](PF6)(2) was determined by X-ray diffraction, and a chiral induction model involving the square-planar palladium complex coordinated with BINAP and a dienophile is proposed.

  DOI：

  10.1021/jo9906680

文献信息

• Asymmetric Hetero Diels−Alder Reaction Catalyzed by Chiral Cationic Palladium(II) and Platinum(II) Complexes
  作者：Shuichi Oi、Eiji Terada、Kazuei Ohuchi、Tomoko Kato、Yukari Tachibana、Yoshio Inoue

  DOI：10.1021/jo9906680

  日期：1999.11.1

  The hetero Diels-Alder reaction of nonactivated conjugated dienes 1 with arylglyoxals 2 and glyoxylate esters 7 proceeded enantioselectively in the presence of a catalytic amount of cationic chiral BINAP-palladium or -platinum complexes and 3 Angstrom molecular sieves (MS3A). The addition of MS3A effectively improved the enantioselectivity of the reaction. Excellent ee's were obtained from the reactions of 2,3-dimethyl-1,3-butadiene (1a) and 1,3-cyclohexadiene (1d) with dienophiles 2 and 7. The square-planar structure of [Pd(S-BINAP)(PhCN)(2)](PF6)(2) was determined by X-ray diffraction, and a chiral induction model involving the square-planar palladium complex coordinated with BINAP and a dienophile is proposed.