2,6-di-n-propyl-γ-pyrone | 14774-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,6-di-n-propyl-γ-pyrone
• 英文别名: 2,6-dipropyl-4H-pyran-4-one；2,6-dipropyl-pyran-4-one；2,6-Dipropyl-pyran-4-on；2,6-dipropylpyran-4-one
• CAS: 14774-16-4
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: MBJBNTAZZNOHJH-UHFFFAOYSA-N

物化性质

• 沸点：
  136 °C(Press: 5 Torr)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-di-n-propyl-γ-pyrone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、2.5 MPa 条件下， 以56%的产率得到cis-tetrahydro-2,6-dipropyl-4H-pyran-4-one
  参考文献：
  名称：

  Diastereoselective Synthesis of cis-2,6-Disubstituted Perhydro-4-pyranones Using Elevated Pressure Hydrogenation

  摘要：

  A diastereoselective strategy for the synthesis of gamma-pyrons was developed, starting from the Mg diacetonedicarboxylate complex. Initial cyclization with suitable anhydrides or acid chlorides, followed by hydrolytic decarboxylation leads to 2,6-disubstituted pyrans. Elevated pressure hydrogenation using Pd/C affords the title compounds in high diastereoselectivity. Scope and limitations of the method are outlined on selected examples.

  DOI：

  10.1007/s00706-005-0317-8
• 作为产物：
  描述：

  在 盐酸 、 sodium carbonate 作用下， 反应 14.0h， 生成 2,6-di-n-propyl-γ-pyrone
  参考文献：
  名称：

  Design of optimized photorefractive polymers: A novel class of chromophores

  摘要：

  It is demonstrated that the microscopic mechanism of the photorefractive (PR) effect in organic composites with low glass transition temperatures involves the formation of refractive index gratings through a space-charge field-modulated Kerr effect. A tensorial formulation of the macroscopic aspects of the PR Kerr effect and its microscopic interpretation is presented. The second-order dipole orientation term containing the anisotropy of the first-order optical polarizability α(−ω;ω) is shown to yield the dominant contribution to the Kerr susceptibility χ(3)(−ω;ω,0,0). A class of special chromophores having negligible second-order polarizabilities β(−ω;ω,0) and large dipole moments μ has been identified in order to optimize this term. These chromophores are not subject to the efficiency-transparency tradeoff typically encountered with second-order nonlinear optical (NLO) chromophores, providing highly transparent materials with large PR Kerr response. Contrary to previous approaches in this field, the best-performing PR polymers are then expected to employ chromophores that would be useless for second- order applications (negligible β). We report PR of the material 30% 2,6-di-n-propyl-4H-pyran-4-ylidenemalononitrile (DPDCP): 15% N,N′-bis(3-methylphenyl)- N,N′-bis(phenyl)benzidine (TPD):55% poly(methyl methacrylate) (PMMA):0.3% C60 as an illustration of this principle. A 100 μm thick film of this material exhibits a steady-state diffraction efficiency of η=25% and net two-beam coupling of Γ=50 cm−1 at a bias field of 100 V/μm and a wavelength of 676 nm. The macroscopic Kerr susceptibility of the material is related to molecular electronic properties of the chromophore DPDCP which were independently determined by experiments in solution and by quantum chemical calculations.

  DOI：

  10.1063/1.472950

文献信息

• Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
  作者：Yi-Feng Qiu、Fang Yang、Zi-Hang Qiu、Mei-Jin Zhong、Li-Jing Wang、Yu-Ying Ye、Bo Song、Yong-Min Liang

  DOI：10.1021/jo402055a

  日期：2013.12.6

  Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

  发现布朗斯台德酸催化的串联环化对于从二炔酮制备一系列多取代的4-吡喃酮非常有效（收率高达99％）。还通过使用NIS和/或布朗斯台德酸选择性地合成了4-吡啶酮和3-吡咯烷酮衍生物。NIS作为亲电子试剂可以在非常温和的反应条件下有效而迅速地促进这些反应。
• Synthesis and Enantioselective Baeyer-Villiger Oxidation of Prochiral Perhydro-pyranones with Recombinant<b> <i>E. coli</i> </b>Producing<b> <i>Cyclohexanone Monooxygenase</i> </b>
  作者：Marko D. Mihovilovic、Florian Rudroff、Wolfgang Kandioller、Birgit Grötzl、Peter Stanetty、Helmut Spreitzer

  DOI：10.1055/s-2003-42035

  日期：——

  Recombinant whole cells of Escherichia coli overex-pressing Acinetobacter sp. NCIMB 9871 cyclohexanone monooxygenase (E.C. 1.14.13.22) have been utilized for the Baeyer-Villiger oxidation of prochiral perhydro-pyranones. The spatial limitations of the enzyme's active site have been estimated by increasing the chain length of cis-substituents in positions 2 and 6. A diastereoselective synthetic sequence

  过表达不动杆菌属的大肠杆菌的重组全细胞。NCIMB 9871 环己酮单加氧酶 (EC 1.14.13.22) 已用于前手性全氢吡喃酮的 Baeyer-Villiger 氧化。已经通过增加位置 2 和 6 中顺式取代基的链长度来估计酶活性位点的空间限制。利用高压氢化开发了所需底物酮的非对映选择性合成序列。
• Atom-Economic Synthesis of 4-Pyrones from Diynones and Water
  作者：Yan-Li Xu、Qing-Hu Teng、Wei Tong、Heng-Shan Wang、Ying-Ming Pan、Xian-Li Ma

  DOI：10.3390/molecules22010109

  日期：——

  Transition-metal-free synthesis of 4-pyrones via TfOH-promoted nucleophilic addition/cyclization of diynones and water has been developed. This transformation is simple, atom economical and environmentally benign, providing rapid and efficient access to substituted 4-pyrones.

  已经开发出通过 TfOH 促进二炔酮和水的亲核加成/环化来无过渡金属合成 4-吡喃酮。这种转化简单、原子经济且环境友好，可快速有效地获得取代的 4-吡喃酮。
• Deshapande, Journal of the Indian Chemical Society, 1932, vol. 9, p. 303,306
  作者：Deshapande

  DOI：——

  日期：——