2-acryloyl-1-ethyl-5,5-dimethylpyrazolidin-3-one | 864379-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-acryloyl-1-ethyl-5,5-dimethylpyrazolidin-3-one
• 英文别名: 2-acryloyl-5,5-dimethyl-1-ethyl-3-pyrazolidinone；1-Ethyl-5,5-dimethyl-2-prop-2-enoylpyrazolidin-3-one；1-ethyl-5,5-dimethyl-2-prop-2-enoylpyrazolidin-3-one
• CAS: 864379-98-6
• 化学式: C₁₀H₁₆N₂O₂
• 分子量: 196.249
• InChiKey: XVEKNUODRWFYIV-UHFFFAOYSA-N

物化性质

• 沸点：
  255.5±23.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acryloyl-1-ethyl-5,5-dimethylpyrazolidin-3-one 、 1-(phenoxycarbonyl)-1,2-dihydropyridine 在 silver hexafluoroantimonate 、 chiral PdCl₂-phosphinooxazolidine 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以42%的产率得到7-(2-Ethyl-3,3-dimethyl-5-oxo-pyrazolidine-1-carbonyl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid 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：

  5,5-二甲基吡唑啉-3-酮 在 potassium carbonate 、 sodium iodide 、 lithium chloride 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 9.0h， 生成 2-acryloyl-1-ethyl-5,5-dimethylpyrazolidin-3-one
  参考文献：
  名称：

  An efficient synthetic methodology of chiral isoquinuclidines by the enantioselective Diels–Alder reaction of 1,2-dihydropyridines using chiral cationic palladium–phosphinooxazolidine catalyst

  摘要：

  High purity chiral isoquinuclidines (97%ee) were obtained from the enantioselective Diels-Alder reaction of 1-phenoxycarbonyl-1,2-dihydropyridine with 1-benzyl-2-acry loylpyrazolidin-3-one using chiral cationic palladiurn-phosphinooxazolidine (Pd-POZ) catalyst. The obtained DA adduct was easily converted to the chiral piperidine derivative bearing three stereogenetic centers in the structure. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.099

文献信息

• Asymmetric Cycloaddition Reactions of Diazoesters with 2-Alkenoic Acid Derivatives Catalyzed by Binaphthyldiimine–Ni(II) complexes
  作者：Hiroyuki Suga、Yasuhisa Furihata、Atsushi Sakamoto、Kennosuke Itoh、Yukihisa Okumura、Teruko Tsuchida、Akikazu Kakehi、Toshihide Baba

  DOI：10.1021/jo201061f

  日期：2011.9.16

  (R)-BINIM-4Ph-2QN (ligand C) and Ni(ClO4)2·6H2O) afforded 2-pyrazolines having a methine carbon substituted with an oxazolidinonyl group in moderate ratios (70:30 to 72:28), along with high enantioselectivities (90–92% ee) via 1,3-proton migration. On the basis of the investigations on the counteranions of the Ni(II) complex, the N-substituent of pyrazolidinone, and reaction temperatures, the optimal enantioselectivity

  评估了手性联萘二胺（BINIM）-Ni（II）配合物对重氮乙酸乙酯与3-丙烯酰基-2-恶唑烷酮和2-（2-烯酰基）-3-吡唑烷二酮衍生物的不对称对映选择性重氮烷环加成反应的催化活性。在BINIM–Ni（II）络合物（10 mol％；由（R）-BINIM-4Ph-2QN（配体C）和Ni（ClO 4）2 ·6H 2O）通过1,3-质子迁移，以中等比例（70:30至72:28）提供了一个被吡唑啉酮基取代的次甲基碳的2-吡唑啉，以及高对映选择性（90-92％ee）。在对Ni（II）络合物的抗衡阴离子，吡唑烷酮的N-取代基和反应温度进行研究的基础上，获得了2-吡唑啉的最佳对映选择性（97％ee）和比率（85:15）。 （R）-BINIM-4Ph-2QN-Ni（II）（（R）-C / Ni（II））存在下2-丙烯酰基-1-苄基-5,5-二甲基-3-吡唑烷酮的反应Ni（BF 4）2 ·6H 2制备的配合物O
• Copper(II)-Catalyzed Exo and Enantioselective Cycloadditions of Azomethine Imines
  作者：Mukund P. Sibi、Digamber Rane、Levi M. Stanley、Takahiro Soeta

  DOI：10.1021/ol800904t

  日期：2008.7.17

  A strategy for exo and enantioselective 1,3-dipolar cycloaddition of azomethine imines to 2-acryloyl-3-pyrazolidinone is described. The corresponding cycloadducts are isolated with high diastereoselectivities (up to >96:4 exo/endo) and enantioselectivities (up to 98% ee).
• An efficient synthetic methodology of chiral isoquinuclidines by the enantioselective Diels–Alder reaction of 1,2-dihydropyridines using chiral cationic palladium–phosphinooxazolidine catalyst
  作者：Hiroto Nakano、Natsumi Tsugawa、Kouichi Takahashi、Yuko Okuyama、Reiko Fujita

  DOI：10.1016/j.tet.2006.08.099

  日期：2006.11

  High purity chiral isoquinuclidines (97%ee) were obtained from the enantioselective Diels-Alder reaction of 1-phenoxycarbonyl-1,2-dihydropyridine with 1-benzyl-2-acry loylpyrazolidin-3-one using chiral cationic palladiurn-phosphinooxazolidine (Pd-POZ) catalyst. The obtained DA adduct was easily converted to the chiral piperidine derivative bearing three stereogenetic centers in the structure. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.