(5E)-dec-5-en-2-one | 42521-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5E)-dec-5-en-2-one
• 英文别名: (E)-dec-5-en-2-one；dec-5t-en-2-one
• CAS: 42521-57-3
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: QYPLUMNWWBFAJS-VOTSOKGWSA-N

物化性质

• 沸点：
  217.0±9.0 °C(Predicted)
• 密度：
  0.836±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式-1-己烯-1-基硼酸 在 acetylacetonatodicarbonylrhodium(l) potassium hydrogen bifluoride 、 1,4-双(二苯基膦)丁烷 作用下， 以 甲醇 、 水 为溶剂， 反应 16.25h， 生成 (5E)-dec-5-en-2-one
  参考文献：
  名称：

  Potassium Alkenyl- and Aryltrifluoroborates:  Stable and Efficient Agents for Rhodium-Catalyzed Addition to Aldehydes and Enones

  摘要：

  [GRAPHICS]Potassium alkenyl- and aryltrifluoroborates undergo addition to enones and aldehydes in the presence of Rh(1) catalysts to give beta-functionalized ketones and allylic/benzylic alcohols, respectively. Reaction proceeds more rapidly than with the corresponding boronic acids, and the choice of phosphine ligand does not signifcantly influence the overall efficiency of addition.

  DOI：

  10.1021/ol9910767

文献信息

• Metal-Catalyzed Release of Supported Boronic Acids for C−C Bond Formation
  作者：Christelle Pourbaix、François Carreaux、Bertrand Carboni

  DOI：10.1021/ol000338y

  日期：2001.3.1

  The viability of solid-supported boronic acids as reagents for Suzuki couplings and nucleophilic additions to aldehydes and enones was successfully demonstrated. This metal-catalyzed cleavage strategy allows the synthesis of a series of functionalized biphenyl products, benzylic alcohols, and beta-substituted ketones.

  成功证明了固体负载的硼酸作为Suzuki偶联剂和向醛和烯酮的亲核加成试剂的可行性。这种金属催化的裂解策略可以合成一系列官能化的联苯产物，苯甲醇和β-取代的酮。
• [EN] USING MIXTURES OF E/Z ISOMERS TO OBTAIN QUANTITATIVELY SPECIFIC PRODUCTS BY COMBINED ASYMMETRIC HYDROGENATIONS<br/>[FR] UTILISATION DE MÉLANGES D'ISOMÈRES E/Z EN VUE D'OBTENIR DES PRODUITS SPÉCIFIQUES DE MANIÈRE QUANTITATIVE PAR HYDROGÉNATIONS ASYMÉTRIQUES COMBINÉES
  申请人：DSM IP ASSETS BV

  公开号：WO2014096106A1

  公开（公告）日：2014-06-26

  The present invention relates to a process of manufacturing compound having stereogenic centres from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centres. The process involves two asymmetric hydrogenation steps. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.

  本发明涉及一种从具有可拆手双键的E/Z异构体混合物中制造具有立体中心的化合物的过程。氢化产物在立体中心处具有特定的期望构型。该过程涉及两个不对称氢化步骤。该过程非常有利，因为它以高效的方式从起始产物的立体异构体混合物中形成所需的手性产物。
• Unsymmetrical Unsaturated Ketones from Lactones and Carboxylic Acids in One Step
  作者：Wolfgang Giersch、Ferdinand Naef

  DOI：10.1002/hlca.200490154

  日期：2004.7

  A one-step transformation of γ- and δ-(spiro)lactones into γ,δ- and δ,ε-unsaturated ketones in the presence of carboxylic acids in the vapor phase at 400° over a supported manganese catalyst is reported for the first time. The scope of this new transformation is exemplified with a series of lactones, and a mechanistic rationale is proposed.

  首次报道了在负载型锰催化剂上在400°C气相存在羧酸的情况下，将γ-和δ-（螺）内酯一步转化为γ，δ-和δ，ε-不饱和酮的过程。时间。该新转化的范围以一系列内酯为例，并提出了机械原理。
• (5<i>E</i>/<i>Z</i>,7<i>E</i>,9)-Decatrien-2-ones, Pineapple-like Flavors from <i>Fomitopsis betulina</i>—Structure Elucidation and Sensorial Properties
  作者：Miriam Grosse、Tim Pendzialeck、Jörg Fohrer、Ralf G. Berger、Ulrich Krings

  DOI：10.1021/acs.jafc.9b06105

  日期：2020.9.23

  and most characteristic pineapple-like odor was found for (5Z,7E,9)-decatrien-2-one. Global minimum energy calculation of the methyl ketones and the comparison to (1,3E,5Z)-undecatriene, a character impact compound of fresh pineapple, showed that a chain length of at least 10 carbon atoms and a terminal double bond embedded in a “L”-shaped conformation were common to compounds imparting an intense pineapple-like

  在农用工业支流上栽培食用菌Fetopsis betulina的过程中，感觉到令人强烈联想到菠萝的令人愉悦的味道。香精提取物稀释分析确定了两种具有明显菠萝味的风味成分。根据质谱数据，进行了（E）-戊-2,4-二烯-1-基三phosph溴化膦与乙酰丙酸乙酯的维蒂希反应。结果（5 E / Z，7 E，9）-癸三烯-2-酮与从真菌培养物中分离的化合物相同。合成了一些结构相关的甲基酮，经核磁共振和质谱法证实，并对其气味进行了表征。对于（5 Z，7 E，9）-十碳三烯-2-酮，发现最低的气味阈值和最典型的菠萝状气味。甲基酮的全球最小能量计算以及与（1,3 E，5 Z）-十一碳三烯（一种新鲜菠萝的特征冲击化合物）的比较表明，链长至少10个碳原子，并且末端嵌入了一个双键“ L”形构象是赋予强烈菠萝状气味的化合物所共有的。两者（5 E / Z，7 E，9）-癸三烯-2-酮尚未被描述为天然香料化合物。
• [EN] PROCESS FOR THE DIRECT CONVERSION OF LACTONES INTO UNSATURATED KETONES OR ALDEHYDES<br/>[FR] PROCEDE DE CONVERSION DIRECTE DE LACTONES EN CETONES OU ALDEHYDES INSATURES
  申请人：FIRMENICH & CIE

  公开号：WO2004089861A1

  公开（公告）日：2004-10-21

  The present invention refers to a process for the preparation of unsaturated ketones or aldehydes by pyrolysis of a lactone, in the presence of a reducing agent such as molecular hydrogen or a carboxylic acid, and in the presence of a catalyst, optionally supported, comprising at least one metal selected from the group consisting of Y, Ti, Cd, Mn, Zn, Sc and Zr.

  本发明涉及一种制备不饱和酮或醛的过程，通过在还原剂（如分子氢或羧酸）存在下，在催化剂的存在下（可选支撑），在至少选择自Y、Ti、Cd、Mn、Zn、Sc和Zr组成的金属中选择的情况下，通过对内酯进行热解实现。