5-异丙基-3-吡唑烷酮 | 174470-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-异丙基-3-吡唑烷酮
• 中文别名: 3-吡唑烷酮,5-(1-甲基乙基)-(9CI)
• 英文名称: 5-isopropyl-3-pyrrazolidinone
• 英文别名: (RS)-5-iso-propylpyrazolidin-3-one；5-Isopropylpyrazolidin-3-one；5-propan-2-ylpyrazolidin-3-one
• CAS: 174470-57-6
• 化学式: C₆H₁₂N₂O
• 分子量: 128.174
• InChiKey: ZBKUUAFRZWBLBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-异丙基-3-吡唑烷酮 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 Methanesulfonic acid 5-isopropyl-1-isopropylcarbamoyl-4,5-dihydro-1H-pyrazol-3-yl ester
  参考文献：
  名称：

  Synthesis, insecticidal and anti-acetylcholinesterase activity of a new class of heterocyclic methanesulfonates

  摘要：

  A series of 3-methanesulfonyloxy-2-pyrazolines were prepared by mesylation of the corresponding pyrazolidin-3-ones, The compounds exhibited strong insecticidal and anti-acetylcholinesterase activity.

  DOI：

  10.1016/0960-894x(95)00562-8
• 作为产物：
  描述：

  (E)-乙基4-甲基戊-2-烯酯 在 肼 作用下， 以 乙醇 为溶剂， 生成 5-异丙基-3-吡唑烷酮
  参考文献：
  名称：

  Synthesis, insecticidal and anti-acetylcholinesterase activity of a new class of heterocyclic methanesulfonates

  摘要：

  A series of 3-methanesulfonyloxy-2-pyrazolines were prepared by mesylation of the corresponding pyrazolidin-3-ones, The compounds exhibited strong insecticidal and anti-acetylcholinesterase activity.

  DOI：

  10.1016/0960-894x(95)00562-8

文献信息

• Structural effects in pyrazolidinone-mediated organocatalytic Diels–Alder reactions
  作者：Eoin Gould、Tomas Lebl、Alexandra M.Z. Slawin、Mark Reid、Andrew D. Smith

  DOI：10.1016/j.tet.2010.09.021

  日期：2010.11

  promoted Diels–Alder reactions evaluated. Systematic variation of the C(5)- and N(2)-substituents indicates that the incorporation of an electron withdrawing substitutent at N(2) and either a Ph or CF3 substitution at C(5) results in optimal catalytic activity. The diastereoisomeric resolution of a model C(5)-Ph substituted pyrazolidinone and its ability to impart modest levels of asymmetric induction

  制备了一系列吡唑烷丁-3-酮，并评估了它们作为亚胺离子促进的Diels-Alder反应的催化剂的活性。C（5）-和N（2）-取代基的系统变化表明，在N（2）引入吸电子取代基和在C（5）取代Ph或CF 3导致最佳的催化活性。还证明了模型C（5）-Ph取代的吡唑烷酮的非对映异构体拆分及其在有机催化Diels-Alder反应中赋予适度水平的不对称诱导的能力。
• Diels−Alder Cycloaddition Strategy for Kinetic Resolution of Chiral Pyrazolidinones
  作者：Mukund P. Sibi、Keisuke Kawashima、Levi M. Stanley

  DOI：10.1021/ol901504p

  日期：2009.9.3

  A rare example of the application of a catalytic, enantioselective Diels−Alder cycloaddition to affect a kinetic resolution has been developed. Chiral pyrazolidinones are resolved with high selectivity through a process that utilizes a relay of stereochemical information from a permanent chiral center to a fluxional chiral center to enhance the inherent selectivity of the chiral Lewis acid catalyst

  已经开发了一个罕见的催化，对映选择性Diels-Alder环加成反应影响动力学拆分的例子。通过利用将立体化学信息从永久性手性中心转移至流动性手性中心以增强手性路易斯酸催化剂的固有选择性的方法，以高选择性拆分手性吡唑烷酮。
• Kinetic Resolutions of Azomethine Imines via Copper-Catalyzed [3 + 2] Cycloadditions
  作者：Andrés Suárez、C. Wade Downey、Gregory C. Fu

  DOI：10.1021/ja052876h

  日期：2005.8.1

  An effective method has been developed for the kinetic resolution of racemic azomethine imines via [3 + 2] cycloadditions with alkynes catalyzed by a chiral copper complex. Efficient kinetic resolution is observed for a variety of N1 and C5 substituents on the dipole, thereby furnishing a wide array of useful enantioenriched azomethine imines, which can readily be transformed into monocyclic and bicyclic pyrazolidinones.
• Synthesis, insecticidal and anti-acetylcholinesterase activity of a new class of heterocyclic methanesulfonates
  作者：George Holan、Chris T. Virgona、Keith G. Watson、Bruce L. Finkelstein

  DOI：10.1016/0960-894x(95)00562-8

  日期：1996.1

  A series of 3-methanesulfonyloxy-2-pyrazolines were prepared by mesylation of the corresponding pyrazolidin-3-ones, The compounds exhibited strong insecticidal and anti-acetylcholinesterase activity.