3-butyryl-4-hydroxy-6-propyl-2H-pyran-2-one | 18742-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-butyryl-4-hydroxy-6-propyl-2H-pyran-2-one
• 英文别名: 3-butanoyl-4-hydroxy-6-propylpyran-2-one
• CAS: 18742-93-3
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: BUBOFHGDORBTTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-butyryl-4-hydroxy-6-propyl-2H-pyran-2-one 在 盐酸 、 乙酸酐 作用下， 反应 14.0h， 生成 2,6-di-n-propyl-4H-pyran-4-ylidenemalononitrile
  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
• 作为产物：
  描述：

  N-acetylcysteamine thioester of β-ketohexanoic acid 在 Aspergillus oryzae acylalkylpyrone synthase CsyB, I₃₇₅F mutant, hydrate form 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.33h， 生成 3-butyryl-4-hydroxy-6-propyl-2H-pyran-2-one
  参考文献：
  名称：

  真菌III型聚酮化合物合酶CsyB由两个β-酮酰基单元形成酰基烷基吡喃酮的结构基础。

  摘要：

  米曲霉的酰基烷基吡喃酮合酶CsyB催化由乙酰乙酰辅酶A，脂肪酰基辅酶A和丙二酰辅酶A一锅形成3-酰基-4-羟基-6-烷基-α-吡喃酮支架。这是第一种III型聚酮化合物合酶，不仅可以进行聚酮化合物链的延伸，还可以使两个β-酮酰基单元缩合。野生型CsyB及其I375F和I375W突变体的晶体结构分别以1.7-，2.3-和2.0-A的分辨率解析。晶体结构揭示了一个独特的活性位点结构，该结构具有迄今无法识别的新颖口袋，可容纳乙酰乙酰辅酶A起始物，此外还具有带有Cys-His-Asn催化三联体的常规延伸/环化口袋和用于结合脂肪的长疏水通道酰基链。该结构还表明存在一个假定的亲核水分子，该分子被氢键网络激活，其活性位点中心处有His-377和Cys-155。此外，体外酶反应证实，H2（18）O分子的（18）O原子通过酶法结合到最终产物中。这些观察结果表明，酶反应是通过将乙酰乙酰辅酶A负载到Cys-155

  DOI：

  10.1074/jbc.m114.626416

文献信息

• Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs
  作者：Leah M. Bouthillette、Catherine A. Darcey、Tess E. Handy、Sarah C. Seaton、Amanda L. Wolfe

  DOI：10.1016/j.bmcl.2017.04.067

  日期：2017.6

  for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50=0.04-3.8µg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50=223-304µg/mL)

  天然产物是具有抗菌活性的结构多样的化合物的丰富来源，可用于开发新型有效的抗生素。一类这样的天然产物是假吡喃酮。在这里，我们介绍了从北卡罗莱纳州西部花园土壤中发现的假单胞菌属物种中分离出假吡喃酮B（2），以及对天然产物的C3和C6烷基类似物对革兰氏阳性和革兰氏阴性细菌的抗菌活性的SAR评估。我们发现抗菌活性和C3 / C6烷基链长之间存在直接关系。为了抑制革兰氏阳性菌，发现6​​至7个碳原子之间的烷基链长度最活跃（IC50 = 0.04-3.8µg / mL），而短链烷基类似物对革兰氏阴性菌的活性中等（IC50 = 223） -304µg / mL）。
• Syntheses of α-Pyrones Using Gold-Catalyzed Coupling Reactions
  作者：Tuoping Luo、Mingji Dai、Shao-Liang Zheng、Stuart L. Schreiber

  DOI：10.1021/ol200794w

  日期：2011.6.3

  Sequential alkyne activation of terminal alkynes and propiolic acids by gold(I) catalysts yields compounds having α-pyrone skeletons. Novel cascade reactions involving propiolic acids are reported that give rise to α-pyrones with different substitution patterns.

  通过金 (I) 催化剂对末端炔烃和丙炔酸进行顺序炔烃活化产生具有 α-吡喃酮骨架的化合物。据报道，涉及丙炔酸的新型级联反应会产生具有不同取代模式的 α-吡喃酮。
• US3989504A
  申请人：——

  公开号：US3989504A

  公开（公告）日：1976-11-02
• Design of optimized photorefractive polymers: A novel class of chromophores
  作者：Rüdiger Wortmann、Constantina Poga、Robert J. Twieg、Christian Geletneky、Christopher R. Moylan、Paul M. Lundquist、Ralph G. DeVoe、Patricia M. Cotts、Hans Horn、Julia E. Rice、Donald M. Burland

  DOI：10.1063/1.472950

  日期：1996.12.15

  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.
• Structural Basis for the Formation of Acylalkylpyrones from Two β-Ketoacyl Units by the Fungal Type III Polyketide Synthase CsyB
  作者：Takahiro Mori、Dengfeng Yang、Takashi Matsui、Makoto Hashimoto、Hiroyuki Morita、Isao Fujii、Ikuro Abe

  DOI：10.1074/jbc.m114.626416

  日期：2015.2

  The acylalkylpyrone synthase CsyB from Aspergillus oryzae catalyzes the one-pot formation of the 3-acyl-4-hydroxy-6-alkyl-alpha-pyrone scaffold from acetoacetyl-CoA, fatty acyl-CoA, and malonyl-CoA. This is the first type III polyketide synthase that performs not only the polyketide chain elongation but also the condensation of two beta-ketoacyl units. The crystal structures of wild-type CsyB and its

  米曲霉的酰基烷基吡喃酮合酶CsyB催化由乙酰乙酰辅酶A，脂肪酰基辅酶A和丙二酰辅酶A一锅形成3-酰基-4-羟基-6-烷基-α-吡喃酮支架。这是第一种III型聚酮化合物合酶，不仅可以进行聚酮化合物链的延伸，还可以使两个β-酮酰基单元缩合。野生型CsyB及其I375F和I375W突变体的晶体结构分别以1.7-，2.3-和2.0-A的分辨率解析。晶体结构揭示了一个独特的活性位点结构，该结构具有迄今无法识别的新颖口袋，可容纳乙酰乙酰辅酶A起始物，此外还具有带有Cys-His-Asn催化三联体的常规延伸/环化口袋和用于结合脂肪的长疏水通道酰基链。该结构还表明存在一个假定的亲核水分子，该分子被氢键网络激活，其活性位点中心处有His-377和Cys-155。此外，体外酶反应证实，H2（18）O分子的（18）O原子通过酶法结合到最终产物中。这些观察结果表明，酶反应是通过将乙酰乙酰辅酶A负载到Cys-155