Undeca-3,8-diene-2,10-dione | 173728-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Undeca-3,8-diene-2,10-dione
• 英文别名: undeca-3,8-diene-2,10-dione
• CAS: 173728-41-1
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: OBMRFRQSZHUVBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  Undeca-3,8-diene-2,10-dione 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-(2-hydroxy-2-methyl-3,3a,4,5,6,6a-hexahydro-1H-pentalen-1-yl)ethanone
  参考文献：
  名称：

  io二碘化物介导的双-α，β-不饱和羰基化合物的分子内环二聚

  摘要：

  investigated（II）二碘化物介导的简单双烯-烯酸酯和-烯酸酯在THF / MeOH中的分子内环二聚。以合成上有用的产率获得包括立体定义的顺式-双环[3.3.0]辛烷和反式-双环[4.3.0]壬烷的螺环和精细的多环产物。

  DOI：

  10.1016/j.tetlet.2009.03.031
• 作为产物：
  描述：

  戊二醛 、 1-三苯基膦-2-丙酮 以 甲苯 为溶剂， 反应 3.0h， 以58%的产率得到Undeca-3,8-diene-2,10-dione
  参考文献：
  名称：

  源自小球蛋白的结构单元和小球蛋白类似物的合成与反应性

  摘要：

  石蒜碱生物碱是独特的（通常在结构上令人印象深刻）多环生物碱，从生物学的角度引起了极大的兴趣，并为全合成提供了理想的靶标。与小丸碱密切相关的丙基哌啶单元参与这些生物碱的生物合成。因此，制备了稳定的颗粒状类化合物，尤其是基于（R）-苯基甘醇的恶唑并哌啶类似物，并研究了它们的反应性。这项工作中描述的化合物扩展了哌啶系列和小丸碱类似物的小结构单元的工具箱，并且可能适合于遵循生物合成策略的合成石蒜碱生物碱。

  DOI：

  10.1016/j.tet.2012.05.051

文献信息

• ortho-Acidic aromatic thiols as efficient catalysts of intramolecular Morita–Baylis–Hillman and Rauhut–Currier reactions
  作者：Philipp S. Selig、Scott J. Miller

  DOI：10.1016/j.tetlet.2010.11.077

  日期：2011.4

  ortho-Mercaptobenzoic acid and ortho-mercaptophenols were discovered as efficient thiol catalysts of both the intramolecular Morita–Baylis–Hillman (MBH) and Rauhut–Currier (RC) reaction. High reaction rates were achieved under mildly basic, aqueous conditions. The unprecedented catalytic activity of these protic nucleophiles could originate from a Brønsted acid induced destabilization of intermediate

  邻-Mercaptobenzoic酸和邻-mercaptophenols被发现既作为分子内森田-的Baylis-希尔曼（MBH）和劳胡特-柯里尔（RC）反应的有效的硫醇的催化剂。在温和的碱性水溶液条件下，可以达到较高的反应速率。这些质子亲核试剂的空前的催化活性可能源自布朗斯台德酸诱导的中间硫醚的去稳定作用，因此代表了多功能路易斯碱催化的独特机理。
• Development of a Cysteine-Catalyzed Enantioselective Rauhut−Currier Reaction
  作者：Carrie E. Aroyan、Alpay Dermenci、Scott J. Miller

  DOI：10.1021/jo101018t

  日期：2010.9.3

  Herein, we report a full account of the development of an enantioselective Rauhut-Currier process that affords products in high yields and enantioselectivities using a cysteine-based catalyst. While traditional Morita-Baylis-Hillman catalysts were found to be essentially ineffective, various derivatives of protected cysteine were found to exhibit extraordinary reactivity and enantiotopic control. Extensive screening of reaction conditions led us to discover the enhanced effects of water as an additive and the chelating power of potassium in achieving higher enantiomer ratios. Mechanistic experiments also provided insight on the potential mechanism of the reaction in addition to possible transition states that provide the absolute stereochemistry formed in the observed products. Also included is a brief survey of the reaction scope involving different ring sizes as well as functionalized substrates.
• Synthesis and reactivity of pelletierine-derived building blocks and pelletierine analogs
  作者：Lok-Hang Yan、Flore Dagorn、Edmond Gravel、Blandine Séon-Méniel、Erwan Poupon

  DOI：10.1016/j.tet.2012.05.051

  日期：2012.8

  units closely related to pelletierine are involved in the biosynthesis of these alkaloids. Therefore, stable pelletierine-like compounds, especially a (R)-phenylglycinol-based oxazolopiperidine analog, were prepared and their reactivity investigated. The compounds described in this work expand the tool-box of small building blocks in the piperidine series and pelletierine analogs and could be suitable

  石蒜碱生物碱是独特的（通常在结构上令人印象深刻）多环生物碱，从生物学的角度引起了极大的兴趣，并为全合成提供了理想的靶标。与小丸碱密切相关的丙基哌啶单元参与这些生物碱的生物合成。因此，制备了稳定的颗粒状类化合物，尤其是基于（R）-苯基甘醇的恶唑并哌啶类似物，并研究了它们的反应性。这项工作中描述的化合物扩展了哌啶系列和小丸碱类似物的小结构单元的工具箱，并且可能适合于遵循生物合成策略的合成石蒜碱生物碱。
• Samarium diiodide-mediated intramolecular cyclodimerisation of bis-α,β-unsaturated carbonyl compounds
  作者：Jonathan R. Powell、Sally Dixon、Mark E. Light、Jeremy D. Kilburn

  DOI：10.1016/j.tetlet.2009.03.031

  日期：2009.7

  Samarium(II) diiodide-mediated intramolecular cyclodimerisation of simple bis-enones and -enoates in THF/MeOH has been investigated. Spirocyclic and elaborated polycyclic products, including stereodefined cis-bicyclo[3.3.0]octane and trans-bicyclo[4.3.0]nonanes, are obtained in synthetically useful yield.

  investigated（II）二碘化物介导的简单双烯-烯酸酯和-烯酸酯在THF / MeOH中的分子内环二聚。以合成上有用的产率获得包括立体定义的顺式-双环[3.3.0]辛烷和反式-双环[4.3.0]壬烷的螺环和精细的多环产物。