2-but-2-enoyl-1-isoquinolin-4-ylmethyl-5,5-dimethyl-pyrazolidin-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-but-2-enoyl-1-isoquinolin-4-ylmethyl-5,5-dimethyl-pyrazolidin-3-one
• 英文别名: 2-[(E)-but-2-enoyl]-1-(isoquinolin-4-ylmethyl)-5,5-dimethylpyrazolidin-3-one
• 化学式: C₁₉H₂₁N₃O₂
• 分子量: 323.395
• InChiKey: ACAFFEBJQUCBAI-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-but-2-enoyl-1-isoquinolin-4-ylmethyl-5,5-dimethyl-pyrazolidin-3-one 、 丙二腈 在 (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 、 magnesium bromide ethyl etherate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到
  参考文献：
  名称：

  Evaluation of Achiral Templates with Fluxional Brønsted Basic Substituents in Enantioselective Conjugate Additions

  摘要：

  Enantioselective conjugate addition of malononitrile to pyrazolidinone-derived enoates proceeds in excellent yields and high enantioselectivities. A comparison of fluxional substituents with and without a Bronsted basic site and their impact on selectivity is detailed. Molecular sieves as an additive were found to be essential to achieve high enantioselectivity.

  DOI：

  10.1021/ol503275w
• 作为产物：
  描述：

  5,5-二甲基吡唑啉-3-酮 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 45.17h， 生成 2-but-2-enoyl-1-isoquinolin-4-ylmethyl-5,5-dimethyl-pyrazolidin-3-one
  参考文献：
  名称：

  Evaluation of Achiral Templates with Fluxional Brønsted Basic Substituents in Enantioselective Conjugate Additions

  摘要：

  Enantioselective conjugate addition of malononitrile to pyrazolidinone-derived enoates proceeds in excellent yields and high enantioselectivities. A comparison of fluxional substituents with and without a Bronsted basic site and their impact on selectivity is detailed. Molecular sieves as an additive were found to be essential to achieve high enantioselectivity.

  DOI：

  10.1021/ol503275w

文献信息

• Evaluation of Achiral Templates with Fluxional Brønsted Basic Substituents in Enantioselective Conjugate Additions
  作者：Shinya Adachi、Norihiko Takeda、Mukund P. Sibi

  DOI：10.1021/ol503275w

  日期：2014.12.19

  Enantioselective conjugate addition of malononitrile to pyrazolidinone-derived enoates proceeds in excellent yields and high enantioselectivities. A comparison of fluxional substituents with and without a Bronsted basic site and their impact on selectivity is detailed. Molecular sieves as an additive were found to be essential to achieve high enantioselectivity.