(R)-(+)-2-benzoyl-4,5-dimethyl-3,6-dihydro-2H-pyran | 253778-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-2-benzoyl-4,5-dimethyl-3,6-dihydro-2H-pyran
• 英文别名: [(2R)-4,5-dimethyl-3,6-dihydro-2H-pyran-2-yl]-phenylmethanone
• CAS: 253778-15-3
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: UQZTZHZDXPQMPU-CYBMUJFWSA-N

物化性质

• 沸点：
  329.5±42.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  (R)-(+)-2-benzoyl-4,5-dimethyl-3,6-dihydro-2H-pyran 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 苯 为溶剂， 反应 17.0h， 生成 2'-Methoxy-[1,1']binaphthalenyl-2-carboxylic acid (R)-((R)-4,5-dimethyl-3,6-dihydro-2H-pyran-2-yl)-phenyl-methyl ester
  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
• 作为产物：
  描述：

  苯基丙醇水合物 、 2,3-二甲基-1,3-丁二烯 在 (BF4)2 、 3 Angstroem MS 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 (R)-(+)-2-benzoyl-4,5-dimethyl-3,6-dihydro-2H-pyran 、 (S)-2-benzoyl-4,5-dimethyl-3,6-dihydro-2H-pyran
  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