(E)-11-hydroxyundec-2-enal | 61618-01-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-11-hydroxyundec-2-enal
• 英文别名: 11-hydroxy-undec-2t-enal
• CAS: 61618-01-7
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: PJSCVXLACFPOHJ-SOFGYWHQSA-N

物化性质

• 沸点：
  313.4±15.0 °C(Predicted)
• 密度：
  0.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  13.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-11-hydroxyundec-2-enal 在 sodium hydroxide 、 silver(l) oxide 作用下， 以 乙醇 为溶剂， 生成 11-Hydroxy-trans-undec-2-en-saeure
  参考文献：
  名称：

  Colonge,J. et al., Bulletin de la Societe Chimique de France, 1963, p. 551 - 553

  摘要：

  DOI：
• 作为产物：
  描述：

  1,8-辛二醇 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 Amberlyst H-15 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 27.0h， 生成 (E)-11-hydroxyundec-2-enal
  参考文献：
  名称：

  Cardillo, Giuliana; Orena, Mario; Porzi, Gianni, Gazzetta Chimica Italiana, 1980, vol. 110, # 9/10, p. 523 - 526

  摘要：

  DOI：

文献信息

• A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines
  作者：Thomas Aubineau、Janine Cossy

  DOI：10.1021/acs.orglett.8b03141

  日期：2018.12.7

  The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji–Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.

  在顺序Pd（0）催化的Tsuji–Trost / Fe（III）催化的杂环化作用下，已从乙烯基环氧乙烷和氨基醇实现了各种取代吗啉的非对映选择性合成。使用相同的策略，获得了2,6-，2,5-和2,3-二取代的吗啉，2,5,6-和2,3,5-三取代的吗啉，收率和非对映选择性都非常好。
• Tetramethylethylenediammonium Bichromate (TMEDADC): A New Selective Oxidation Reagent
  作者：S. Chandrasekhar、Mohamed Takhi、Suchismita Mohapatra

  DOI：10.1080/00397919608003816

  日期：1996.11

  Abstract TMEDADC obtained from Chromium trioxide and TMEDA has been conveniently utilized for the selective oxidation of benzylic and allylic alcohols in excellent yield for the first time.

  摘要 从三氧化铬和 TMEDA 中获得的 TMEDADC 首次以优异的收率方便地用于苯甲醇和烯丙醇的选择性氧化。
• SYNTHESIS OF α,β-UNSATURATED CARBONYLS FROM ALKENES VIA SULFONIUM INTERMEDIATES AND THEIR APPLICATION IN THE SYNTHESIS OF CONJUGATED DIENE PHEROMONES, KAIROMONES, AND RELATED COMPOUNDS
  申请人：[en]TERMÉSZETTUDOMÁNYI KUTATÓKÖZPONT

  公开号：WO2024105421A1

  公开（公告）日：2024-05-23

  α,β-Unsaturated aldehydes are useful products as such in agrochemistry, but also potential intermediates for the preparation of important insect pheromones and kairomones. Until now, primarily the thermodynamically more stable (E)-α,β-unsaturated aldehydes have been identified as useful intermediates in the production of conjugated diene pheromone compounds, however, their practical and cost-effective synthesis on an industrial scale remains challenging. The problem to be solved by the present invention is to provide a method for selective oxidation of alkenes to α,β-unsaturated carbonyls which can be further transformed into pheromones and kairomones preferably without isolation and significant loss of the existing stereochemical purity.