benzyl (1S,4S,7S)-7-[3,3-dimethyl-2-(naphthalen-1-ylmethyl)-5-oxopyrazolidine-1-carbonyl]-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate | 1449396-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzyl (1S,4S,7S)-7-[3,3-dimethyl-2-(naphthalen-1-ylmethyl)-5-oxopyrazolidine-1-carbonyl]-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate
• CAS: 1449396-60-4
• 化学式: C₃₂H₃₃N₃O₄
• 分子量: 523.632
• InChiKey: KWZUVWGLWDRYHX-UIUQJESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(1-naphthylmethyl)-5,5-dimethyl-pyrazolidin-3-one 在 copper(II) bis(trifluoromethanesulfonate) 、 lithium chloride 、 S-4,5-二氢-2-(2-((S)-4,5-二氢-4-异丙基噁唑-2-基)丙-2-基)-4-异丙基噁唑 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 benzyl (1S,4S,7S)-7-[3,3-dimethyl-2-(naphthalen-1-ylmethyl)-5-oxopyrazolidine-1-carbonyl]-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate
  参考文献：
  名称：

  Highly Enantioselective Synthesis of Isoquinuclidine by Diels-Alder Reaction of 1,2-Dihydropyridine Utilizing Chiral Bisoxazoline-Cu(II) Complex

  摘要：

  The enantioselective Diels-Alder (D-A) reaction between N-phenoxycarbonyl- or N-benzyloxycarbonyl-1,2-dihydropyridine (1a or 1b) and N(2)-acryloyl-N(1)-(1-naphthylmethyl)-5,5-dimethylpyrazolidin-3-one (2b) using (S,S)-bisoxazoline-Cu(II) catalyst (A, B, C or D) has been investigated. Utilizing (S,S)-t-Bu-bisoxazoline-Cu(II) catalyst C, the D-A reaction of la and 2 afforded the endo-(7S)-isoquinuclidines (3, 4 or 5) in good chemical yields with high enantioselectivity (up to 99% e.e.).

  DOI：

  10.3987/com-12-s(n)2

文献信息

• Highly Enantioselective Synthesis of Isoquinuclidine by Diels-Alder Reaction of 1,2-Dihydropyridine Utilizing Chiral Bisoxazoline-Cu(II) Complex
  作者：Haruo Matsuyama、Chigusa Seki、Takashi Shimizu、Masafumi Hirama、Hiroto Nakano、Koji Uwai、Nobuhiro Takano、N. D. M. Romauli Hutabarat、Yoshihito Kohari、Eunsang Kwon

  DOI：10.3987/com-12-s(n)2

  日期：——

  The enantioselective Diels-Alder (D-A) reaction between N-phenoxycarbonyl- or N-benzyloxycarbonyl-1,2-dihydropyridine (1a or 1b) and N(2)-acryloyl-N(1)-(1-naphthylmethyl)-5,5-dimethylpyrazolidin-3-one (2b) using (S,S)-bisoxazoline-Cu(II) catalyst (A, B, C or D) has been investigated. Utilizing (S,S)-t-Bu-bisoxazoline-Cu(II) catalyst C, the D-A reaction of la and 2 afforded the endo-(7S)-isoquinuclidines (3, 4 or 5) in good chemical yields with high enantioselectivity (up to 99% e.e.).