[C1-(18)O]-3-benzyl-2-hydroxy-cyclopent-2-en-1-one | 1330064-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [C1-(18)O]-3-benzyl-2-hydroxy-cyclopent-2-en-1-one
• 英文别名: 3-benzyl-2-hydroxycyclopent-2-en-1-(18O)one
• CAS: 1330064-93-1
• 化学式: C₁₂H₁₂O₂
• 分子量: 190.227
• InChiKey: QDZZKNIAXGCWQL-ALWQSETLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [C1-(18)O]-3-benzyl-2-hydroxy-cyclopent-2-en-1-one 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 68.33h， 以17%的产率得到
  参考文献：
  名称：

  Oxidation of cyclopentane-1,2-dione: a study with 18O labeled reagents

  摘要：

  The asymmetric oxidation of 3-alkyl-cyclopentane-1,2-diones with the Ti((OPr)-Pr-i)(4)/tartaric ester/t-BuOOH complex, which gives, in a cascade process, highly enantiomerically enriched gamma-lactone acids, was studied by O-18 isotopic labeling in the substrate and in the oxidant. The path of the labeled atoms was followed by C-13 NMR spectroscopy. It was found that the oxidative ring cleavage of 1,2-dione proceeds via a Baeyer-Villiger-type oxidation mechanism. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.036
• 作为产物：
  描述：

  3-苄基-2-羟基环戊烯-2-酮 在 盐酸 、 重氧水 作用下， 以 1,4-二氧六环 、 二氧六环-d8 为溶剂， 反应 60.0h， 以96%的产率得到[C1-(18)O]-3-benzyl-2-hydroxy-cyclopent-2-en-1-one
  参考文献：
  名称：

  Oxidation of cyclopentane-1,2-dione: a study with 18O labeled reagents

  摘要：

  The asymmetric oxidation of 3-alkyl-cyclopentane-1,2-diones with the Ti((OPr)-Pr-i)(4)/tartaric ester/t-BuOOH complex, which gives, in a cascade process, highly enantiomerically enriched gamma-lactone acids, was studied by O-18 isotopic labeling in the substrate and in the oxidant. The path of the labeled atoms was followed by C-13 NMR spectroscopy. It was found that the oxidative ring cleavage of 1,2-dione proceeds via a Baeyer-Villiger-type oxidation mechanism. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.036

文献信息

• Oxidation of cyclopentane-1,2-dione: a study with 18O labeled reagents
  作者：Indrek Reile、Anne Paju、Aleksander-Mati Müürisepp、Tõnis Pehk、Margus Lopp

  DOI：10.1016/j.tet.2011.06.036

  日期：2011.8

  The asymmetric oxidation of 3-alkyl-cyclopentane-1,2-diones with the Ti((OPr)-Pr-i)(4)/tartaric ester/t-BuOOH complex, which gives, in a cascade process, highly enantiomerically enriched gamma-lactone acids, was studied by O-18 isotopic labeling in the substrate and in the oxidant. The path of the labeled atoms was followed by C-13 NMR spectroscopy. It was found that the oxidative ring cleavage of 1,2-dione proceeds via a Baeyer-Villiger-type oxidation mechanism. (C) 2011 Elsevier Ltd. All rights reserved.