7-(2-oxo-oxazolidine-3-carbonyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester | 502162-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 7-(2-oxo-oxazolidine-3-carbonyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester
• 英文别名: phenyl (1R,4R,7R)-7-(2-oxo-1,3-oxazolidine-3-carbonyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate
• CAS: 502162-95-0
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: KCTLDLBQCRBGAP-NWANDNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯甲醇 、 7-(2-oxo-oxazolidine-3-carbonyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以38%的产率得到(1R,4R,6R)-2-Aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 6-benzyl ester 2-phenyl ester
  参考文献：
  名称：

  The highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine using chiral cationic palladium–phosphinooxazolidine catalyst for the synthesis of chiral isoquinuclidines

  摘要：

  The enantio selective Diets-Alder reactions of 1-phenoxycarbonyl-1,2-dihydropyridine with 1-alkylated acryloyl-pyrazolidin-3-ones using chiral cationic palladium-phosphinooxazolidine (Pd-POZ) catalyst afforded chiral isoquinuclidines with excellent enantioselectivity (up to 97% ee). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.089
• 作为产物：
  描述：

  1-(phenoxycarbonyl)-1,2-dihydropyridine 、 3-丙烯酰基-2-唑烷酮 在 chiral palladium-phosphinooxazolidine hexafluoroantimonate 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到7-(2-oxo-oxazolidine-3-carbonyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester
  参考文献：
  名称：

  在离子液体中重复使用手性阳离子Pd-膦基恶唑烷催化剂：高效催化不对称Diels-Alder反应。

  摘要：

  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）。

  DOI：

  10.1039/b611228e

文献信息

• Asymmetric synthesis of isoquinuclidines by Diels–Alder reaction of 1,2-dihydropyridine utilizing a chiral Lewis acid catalyst
  作者：Chigusa Seki、Masafumi Hirama、N.D.M. Romauli Hutabarat、Junko Takada、Chonticha Suttibut、Hideto Takahashi、Takuya Takaguchi、Yoshihito Kohari、Hiroto Nakano、Koji Uwai、Nobuhiro Takano、Mitsukuni Yasui、Yuko Okuyama、Mitsuhiro Takeshita、Haruo Matsuyama

  DOI：10.1016/j.tet.2011.12.041

  日期：2012.2

  (up to 97% de) by Diels–Alder reaction of 1 with (4R)-2 using Cu(OTf)2/(4S,4′S)-bis(oxazoline) catalyst 8 as a chiral Lewis acid catalyst in dichloromethane at 0 °C. In these reactions, the choice of solvent and the combination of titanium-(2R,3R)-TADDOLate 4 or Cu(II)/(4S,4′S)-bis(oxazoline) 8} and dienophile (4S)-2 or (4R)-2} are very important. The stereochemistry of endo-(7R)-3 has been established

  通过1-（苯氧羰基）的Diels-Alder反应，高收率地获得了手性异喹啉环衍生物2-氮杂双环[2.2.2]辛烷环系统，内-（7 R）-3，具有极好的非对映选择性（高达92％de） ）-1,2-二氢吡啶1与N-丙烯酰基-（4 S）-4-苄基恶唑烷-2--2- （4 S）-2的反应，使用钛-（2 R，3 R）-TADDOLate 4作为手性路易斯酸催化剂在0°C的甲苯中。另一方面，内-（7 S）-3通过使用Cu（OTf）2 /（4 S，4 'S）-双（恶唑啉）催化剂与1（4 R）-2进行Diels-Alder反应，以良好的非对映选择性（高达97％de）获得了高收率的化合物。在0°C下为二氯甲烷中的8手性路易斯酸催化剂。在这些反应中，选择溶剂以及钛-（2 R，3 R）-TADDOLate 4 or Cu（II）/（4 S，4 'S）-双（恶唑啉）8 }和亲二烯体的组合（4 S）-2 或（4
• Reactivity and Efficient Recycling of a Chiral Pd-BINAP Catalyst for Catalytic Asymmetric Diels-Alder Reaction in Ionic Liquid
  作者：Hiroto Nakano、Mitsuhiro Takeshita、Yasuhiro Nishiuchi、Yuta Araki、Reiko Fujita、Koji Uwai、Rina Sato

  DOI：10.3987/com-08-s(f)119

  日期：——

  Chiral cationic palladium-BINAP catalyst in ionic liquid showed an excellent asymmetric catalytic activity in the Diels-Alder reactions using several dienes and the catalyst was easily recycled 7 times with good chemical yield and excellent enantioselectivity (50-60%, 94-98% ee).
• The first catalytic enantioselective Diels–Alder reactions of 1,2-dihydropyridine: efficient syntheses of optically active 2-azabicyclo[2.2.2]octanes with chiral BINAM derived Cr(III) salen complexes
  作者：Norito Takenaka、Yong Huang、Viresh H. Rawal

  DOI：10.1016/s0040-4020(02)00980-8

  日期：2002.10

  We have synthesized a new family of enantiomerically enriched BINAM-derived Schiff base Cr(III) complexes and evaluated them as catalysts for Diels-Alder reactions. These complexes effectively catalyze, for the first time, the enantioselective Diels-Alder reactions between 1,2-dihydropyridine and N-acryloyloxazolidinone to afford 2-azabicyclo[2.2.2]octanes in high yields (89-99%) and with moderate to good enantioselectivities (79-85%). (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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）。
• The highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine using chiral cationic palladium–phosphinooxazolidine catalyst for the synthesis of chiral isoquinuclidines
  作者：Hiroto Nakano、Natsumi Tsugawa、Reiko Fujita

  DOI：10.1016/j.tetlet.2005.06.089

  日期：2005.8

  The enantio selective Diets-Alder reactions of 1-phenoxycarbonyl-1,2-dihydropyridine with 1-alkylated acryloyl-pyrazolidin-3-ones using chiral cationic palladium-phosphinooxazolidine (Pd-POZ) catalyst afforded chiral isoquinuclidines with excellent enantioselectivity (up to 97% ee). (c) 2005 Elsevier Ltd. All rights reserved.