1,1-bis{2-[(4R)-(1-naphthyl)-5,5-dimethyloxazolinyl]}cyclopropane

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1-bis{2-[(4R)-(1-naphthyl)-5,5-dimethyloxazolinyl]}cyclopropane
• 英文别名: (4R)-2-[1-[(4R)-5,5-dimethyl-4-naphthalen-1-yl-4H-1,3-oxazol-2-yl]cyclopropyl]-5,5-dimethyl-4-naphthalen-1-yl-4H-1,3-oxazole
• 化学式: C₃₃H₃₂N₂O₂
• 分子量: 488.629
• InChiKey: YLQTWBLMZLDOIE-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  37.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.18
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,1-环丙基二羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 对二甲苯 为溶剂， 反应 7.05h， 生成 1,1-bis{2-[(4R)-(1-naphthyl)-5,5-dimethyloxazolinyl]}cyclopropane
  参考文献：
  名称：

  Studies of Copper−Bisoxazoline-Catalyzed Asymmetric Cyclopropanation of 2,5-Dimethyl-2,4-hexadiene

  摘要：

  In the [bis{(4R)-(1-naphthyl)-5,5-diniethyloxazoline}/copper]catalyzed asymmetric cyclopropanation of 2,5-dimethyl-2,4-hexadiene with tert-butyl diazoacetate, the effects of a counterion of the copper complex were studied. The[CuCl/bisoxazoline/ Ph3CPF6] catalyst was found to enhance both the catalytic efficiency and the stereoselectivity (the catalyst 0.2 mol %, yield 92%, trans/cis = 88/12, 96% ee for the trans product), compared to our previously reported CuOTf/bisoxazoline catalyst. The density functional calculations were performed to elucidate the effects of the counterion as well as the effects of the gem-dimethyl groups at the 5-position on the bisoxazoline ligand.

  DOI：

  10.1021/op050203d

文献信息

• Studies of Copper−Bisoxazoline-Catalyzed Asymmetric Cyclopropanation of 2,5-Dimethyl-2,4-hexadiene
  作者：Makoto Itagaki、Katsuhisa Masumoto、Katsuhiro Suenobu、Yohsuke Yamamoto

  DOI：10.1021/op050203d

  日期：2006.3.1

  In the [bis(4R)-(1-naphthyl)-5,5-diniethyloxazoline}/copper]catalyzed asymmetric cyclopropanation of 2,5-dimethyl-2,4-hexadiene with tert-butyl diazoacetate, the effects of a counterion of the copper complex were studied. The[CuCl/bisoxazoline/ Ph3CPF6] catalyst was found to enhance both the catalytic efficiency and the stereoselectivity (the catalyst 0.2 mol %, yield 92%, trans/cis = 88/12, 96% ee for the trans product), compared to our previously reported CuOTf/bisoxazoline catalyst. The density functional calculations were performed to elucidate the effects of the counterion as well as the effects of the gem-dimethyl groups at the 5-position on the bisoxazoline ligand.