spiro(cyclopentane-1,1'-tetralan)-2,5-dione | 152654-97-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: spiro(cyclopentane-1,1'-tetralan)-2,5-dione
• 英文别名: 3',4'-dihydro-2'H-spiro[cyclopentane-1,1'-naphthalene]-2,5-dione；spiro[2,3-dihydro-1H-naphthalene-4,2'-cyclopentane]-1',3'-dione
• CAS: 152654-97-2
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: RNNLQZIGLALRPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  spiro(cyclopentane-1,1'-tetralan)-2,5-dione 在 溴 、 碳酸氢钠 作用下， 以 溶剂黄146 、 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到spiro(3-cyclopentene-1,1'-tetralan)-2,5-dione
  参考文献：
  名称：

  Sudini; Khire; Pandey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 10, p. 738 - 745

  摘要：

  DOI：
• 作为产物：
  描述：

  二(三甲基硅氧基)环丁烯 、 spiro(tetralane-2,1'-5,5-diethyl-1,3-dioxane) 在 三氟化硼乙醚 作用下， 生成 spiro(cyclopentane-1,1'-tetralan)-2,5-dione
  参考文献：
  名称：

  Efficient photochemical transformation of spiro[4.n]-2,5-diones to γ-alkylidene γ-butyrolactones: its relevance to photostability of Fredericamycin A

  摘要：

  在 300 nm 的各种溶剂中照射与抗肿瘤抗生素 Fredericamycin A 相关的各种模型螺环酮，可提供 γ-亚烷基 γ-丁内酯的定量产率；讨论了它与 Fredericamycin 的典型形状改变、光稳定性和随后的生物反应的相关性。

  DOI：

  10.1039/c39930000870

文献信息

• Copper(I)-Catalyzed Asymmetric Desymmetrization: Synthesis of Five-Membered-Ring Compounds Containing All-Carbon Quaternary Stereocenters
  作者：Kohsuke Aikawa、Tatsuya Okamoto、Koichi Mikami

  DOI：10.1021/ja3032345

  日期：2012.6.27

  A highly stereoselective catalytic alkylation sequence for the synthesis of highly functionalized and versatile five-membered-ring compounds bearing all-carbon quaternary stereocenters was developed. Enantioselective desymmetrization of achiral cyclopentene-1,3-diones was thus executed by chiral Cu-phosphoramidite catalysts. A variety of complicated cyclopentane derivatives can be synthesized with

  开发了一种高度立体选择性催化烷基化序列，用于合成具有全碳四元立体中心的高度功能化和多功能的五元环化合物。因此，手性 Cu-亚磷酰胺催化剂实现了非手性环戊烯-1,3-二酮的对映选择性去对称化。可以在一锅操作中使用低催化剂负载量合成具有优异立体选择性的各种复杂的环戊烷衍生物。
• Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones
  作者：Tracy J. Jenkins、D. Jean Burnell

  DOI：10.1021/jo00085a041

  日期：1994.3

  Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.
• The BF₃·Et₂O-Catalyzed Reaction of 1,2-Bis[(trimethylsilyl)oxy]cyclobutene and Analogues with Aromatic Ketones
  作者：Sheldon N. Crane、D. Jean Burnell

  DOI：10.1021/jo971867r

  日期：1998.2.1