trans-1-Phenyl-3-nonen-5-one | 141191-77-7

• 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: trans-1-Phenyl-3-nonen-5-one
• 英文别名: (E)-1-phenylnon-3-en-5-one；1-phenyl-3-nonen-5-one
• CAS: 141191-77-7
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: BGMYLAJANATSRK-MDWZMJQESA-N

物化性质

• 沸点：
  340.0±21.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3-Hydroxy-1-phenyl-nonan-5-one 在 bis<3,5-bis(trifluoromethyl)phenyl>borinic acid 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到trans-1-Phenyl-3-nonen-5-one
  参考文献：
  名称：

  Diarylborinic Acids as Efficient Catalysts for Selective Dehydration of Aldols

  摘要：

  芳基上带有吸电子取代基的二芳基硼酸是高效的路易斯酸催化剂，用于 Mukaiyama 羟醛缩合以及在顺式羟醛存在下选择性脱水为 α,β-烯酮。二芳基硼酸的路易斯酸度远高于相应的芳基硼酸。

  DOI：

  10.1055/s-1997-3207

文献信息

• One-Pot Consecutive Reactions Based on the Synthesis of Conjugated Enones by the Re-Catalysed Meyer-Schuster Rearrangement
  作者：Elio Mattia、Alessio Porta、Valentina Merlini、Giuseppe Zanoni、Giovanni Vidari

  DOI：10.1002/chem.201201639

  日期：2012.9.17

  Re catalysis in one‐pot reactions: An atom‐economical, one‐pot strategy that involves alkyne deprotonation and a subsequent rhenium(V)‐catalysed Meyer–Schuster rearrangement of the alkynol to provide α,ß‐unsaturated enones in high yield has been developed (see scheme). Subsequent in situ hydride reduction or Diels–Alder reaction of the enones provided products in good‐to‐high overall yields.

  单锅反应中的重催化：一种原子经济的单锅策略，涉及炔烃去质子化和随后and（V）催化的炔诺醇的Meyer-Schuster重排，以提供高产率的α，ß-不饱和烯酮开发（请参阅计划）。随后进行的烯酮的原位氢化物还原或Diels-Alder反应可提供高至高总收率的产品。
• Direct Access to α,β-Unsaturated Ketones via Rh/MgCl₂-Mediated Acylation of Vinylsilanes
  作者：Xue-Zu Deng、Zi-Yan Chen、Yang Song、Fei Xue、Motoki Yamane、Yan-Ni Yue

  DOI：10.1021/acs.joc.1c01205

  日期：2021.9.17

  We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized

  我们在此报告了通过铑催化的乙烯基硅烷与易得且丰富的羧酸的直接酰化来构建 α,β-不饱和酮的简便实用的结构。该协议的特点是可以访问各种综合有用的功能，并具有中等至出色的产量。更重要的是，药物的后期功能化也以合成有用的产率实现。
• Rearrangement of Allylic and Propargylic Alcohols Catalyzed by the Combined Use of tetrabutylammonium perrhenate (VII) and p-toluenesulfonic acid
  作者：Koichi Narasaka、Hiroyuki Kusama、Yujiro Hayashi

  DOI：10.1016/s0040-4020(01)88874-8

  日期：1992.1

  Allylic rearrangement and/or dehydration reaction of allylic alcohols proceeds smoothly by the use of catalytic amounts of tetrabutylammonium perrhenate and p-toluenesulfonic acid hydrate. Treatment of propargylic alcohols with the catalysts at room temperature affords the rearranged products, α,β-unsaturated carbonyl compounds, while, β,γ-unsaturated ketones are obtained as main products by the reaction

  通过使用催化量的高丁基酸四丁铵和对甲苯磺酸水合物，使烯丙醇的烯丙基重排和/或脱水反应顺利进行。在室温下用催化剂处理炔丙醇可得到重排产物α，β-不饱和羰基化合物，而β，γ-不饱和酮是通过在1，2-二氯乙烷中回流反应得到的主要产物。还描述了该催化体系在某些合成中间体的制备中的应用。
• 2-Benzothiazolyl Propargyl Sulfides: Versatile Precursors for Enantiopure Allenes, E-α,β-Unsaturated Ketones and Z-Sulfonylalkenes
  作者：Dagmar Kapeller、Philip Kocienski

  DOI：10.1055/s-0030-1258259

  日期：2010.11

  described. The approach proceeds via a retro-ene reaction, initiated by lithium aluminium hydride mediated cleavage of benzothiazole from the respective (chiral) 2-benzothiazolyl propargyl sulfone precursors. As such, allenes in up to 92% yield are formed under evolution of sulfur dioxide at ambient temperature. Furthermore, a new and mild way to generate E-α,β-unsaturated ketones has been discovered. These

  描述了一种新颖的立体定向路线，通往丙二烯。该方法通过逆烯反应进行，该反应由氢化锂铝介导的从各自的（手性的）2-苯并噻唑基炔丙基砜前体裂解苯并噻唑而引发。这样，在环境温度下，在释放出二氧化硫的情况下，生成了高达92％收率的丙二烯。此外，已经发现了产生E -α，β-不饱和酮的新的温和方法。通过在室温下用过氧化氢和催化量的钼酸铵处理2-苯并噻唑基炔丙基硫醚，可以约50％的产率形成这些底物。在研究过程中，还发现用硼氢化钠处理2-苯并噻唑基炔丙基砜可导致三键只还原为氢键。Z-双键。 丙二烯-α，β-不饱和酮-氧化-重排-砜
• Mo−Au Combo Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols into α,β-Unsaturated Carbonyl Compounds
  作者：Masahiro Egi、Yoshiko Yamaguchi、Noboru Fujiwara、Shuji Akai

  DOI：10.1021/ol800596c

  日期：2008.5.1

  The combination of Mo and cationic Au catalysts dramatically accelerated the rearrangement of diverse propargyl alcohols, which includes a short reaction time, mild conditions, and high product yields. A practical application to the highly challenging primary propargyl alcohols and the N-alkynyl amides is achieved.