trans-1-Phenyl-4-tert-butylbut-2-ene-1,4-dione | 177093-14-0

• 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-4-tert-butylbut-2-ene-1,4-dione
• 英文别名: (E)-5,5-dimethyl-1-phenylhex-2-ene-1,4-dione
• CAS: 177093-14-0
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: YNPFIPJTERVPJG-MDZDMXLPSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  327.0±34.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  trans-1-Phenyl-4-tert-butylbut-2-ene-1,4-dione 在 sodium hydroxide 、 immobilised poly-L-leucine 、 双氧水 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以75%的产率得到1-((2R,3R)-3-Benzoyl-oxiranyl)-2,2-dimethyl-propan-1-one
  参考文献：
  名称：

  Development of the Juliá asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters

  摘要：

  Polyleucine-based systems have been used to catalyse the asymmetric oxidation of a variety of alkyl enones 1-4,9-14, an enynone 16 and a dienone 17 to afford the corresponding epoxides 5-8, 18-26 in good to excellent yield and optical purity. A range of enediones 30-32, 34 and one unsaturated keto ester 33 have also been epoxidised stereoselectively to afford optically active epoxides 35-39. The epoxidations were carried out with basic peroxide as the oxidant; the polyleucine catalyst was prepared from leucine N-carboxyanhydride using 1,3-diaminopropane, water (employing a humidity cabinet) or a polystyrene immobilised amine as the initiator. Preliminary mass spectral data on material derived from L-leucine and 1,3-diaminopropane (DAP-PLL) suggest that the catalyst consists of material that contains 22 +/- 10 leucine residues.

  DOI：

  10.1039/p19960002837
• 作为产物：
  描述：

  2,2-dimethyl-6-phenylhexan-3-one 在 氧气 、 copper diacetate 、 palladium diacetate 、 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以81%的产率得到trans-1-Phenyl-4-tert-butylbut-2-ene-1,4-dione
  参考文献：
  名称：

  酮的好氧氧化脱氢成1,4-烯酮

  摘要：

  通过钯催化的氧化脱氢，已经开发出一种有效且空前的从饱和酮合成1,4-二烯酮的策略。该协议采用分子氧作为唯一的氧化剂，代表了原子经济和逐步经济的过程。该方法显示出广泛的底物范围，良好的官能团耐受性和完全的E-立体选择性。通过氘标记实验和中间实验研究了反应机理。

  DOI：

  10.1021/acs.orglett.0c04174

文献信息

• Unexpected asymmetric epoxidation reactions catalysed by polyleucine-based systems
  作者：Wolfgang Kroutil、Patrick Mayon、M. Elena Lasterra-Sánchez、Samuel J. Maddrell、Stanley M. Roberts、Steven R. Thornton、Christine J. Todd、Melek Tüter

  DOI：10.1039/cc9960000845

  日期：——

  Polyleucine-based systems have been shown to catalyse the asymmetric epoxidation of a variety of enones, an enynone, selected enediones and an unsaturated ketoester.
• Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones
  作者：Bao-Yin Zhao、Xing-Long Zhang、Rui-Li Guo、Meng-Yue Wang、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.0c04174

  日期：2021.2.19

  An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism

  通过钯催化的氧化脱氢，已经开发出一种有效且空前的从饱和酮合成1,4-二烯酮的策略。该协议采用分子氧作为唯一的氧化剂，代表了原子经济和逐步经济的过程。该方法显示出广泛的底物范围，良好的官能团耐受性和完全的E-立体选择性。通过氘标记实验和中间实验研究了反应机理。
• Development of the Juliá asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters
  作者：Wolfgang Kroutil、M. Elena Lasterra-Sánchez、Samuel J. Maddrell、Patrick Mayon、Phillip Morgan、Stanley M. Roberts、Steven R. Thornton、Christine J. Todd、Melek Tüter

  DOI：10.1039/p19960002837

  日期：——

  Polyleucine-based systems have been used to catalyse the asymmetric oxidation of a variety of alkyl enones 1-4,9-14, an enynone 16 and a dienone 17 to afford the corresponding epoxides 5-8, 18-26 in good to excellent yield and optical purity. A range of enediones 30-32, 34 and one unsaturated keto ester 33 have also been epoxidised stereoselectively to afford optically active epoxides 35-39. The epoxidations were carried out with basic peroxide as the oxidant; the polyleucine catalyst was prepared from leucine N-carboxyanhydride using 1,3-diaminopropane, water (employing a humidity cabinet) or a polystyrene immobilised amine as the initiator. Preliminary mass spectral data on material derived from L-leucine and 1,3-diaminopropane (DAP-PLL) suggest that the catalyst consists of material that contains 22 +/- 10 leucine residues.