3-己基-4-羟基-6-戊基-2-吡喃酮 | 107617-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-己基-4-羟基-6-戊基-2-吡喃酮
• 英文名称: 3-hexanoyl-4-hydroxy-6-pentyl-2H-pyran-2-one
• 英文别名: 3-Hexanoyl-4-hydroxy-6-pentylpyran-2-one
• CAS: 107617-14-1
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: BWVBXGFQVUKUCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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-己基-4-羟基-6-戊基-2-吡喃酮 在 硫酸 作用下， 反应 1.0h， 以43%的产率得到4-羟基-6-戊基吡喃-2-酮
  参考文献：
  名称：

  脂肪酸合成的天然产物抑制剂：海洋微生物代谢产物假吡喃酮A和B的合成及其抗感染活性的评估

  摘要：

  使用甲基β-氧代羧酸酯原料已完成标题天然产物假吡喃酮A（1）和B（2）的总合成。天然产物和少量组结构上相关的化合物用于针对一系列病原微生物的生长抑制活性进行了评价，发现其显示出良好的效力（IC 50 ≥0.46微克/毫升），并选择性向杜氏利什曼原虫。几种化合物抑制了恶性疟原虫和结核分枝杆菌的重组脂肪酸生物合成酶，从而在寻找新的抗感染药时验证了这些靶标。

  DOI：

  10.1016/j.tet.2007.11.075
• 作为产物：
  描述：

  3-氧代辛酸 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以21%的产率得到3-己基-4-羟基-6-戊基-2-吡喃酮
  参考文献：
  名称：

  脂肪酸合成的天然产物抑制剂：海洋微生物代谢产物假吡喃酮A和B的合成及其抗感染活性的评估

  摘要：

  使用甲基β-氧代羧酸酯原料已完成标题天然产物假吡喃酮A（1）和B（2）的总合成。天然产物和少量组结构上相关的化合物用于针对一系列病原微生物的生长抑制活性进行了评价，发现其显示出良好的效力（IC 50 ≥0.46微克/毫升），并选择性向杜氏利什曼原虫。几种化合物抑制了恶性疟原虫和结核分枝杆菌的重组脂肪酸生物合成酶，从而在寻找新的抗感染药时验证了这些靶标。

  DOI：

  10.1016/j.tet.2007.11.075

文献信息

• Gold-catalyzed homo- and cross-annulation of alkynyl carboxylic acids: a facile access to substituted 4-hydroxy 2<i>H</i>-pyrones and total synthesis of pseudopyronine A
  作者：Gayyur、Shivani Choudhary、Anchal Saxena、Nayan Ghosh

  DOI：10.1039/d0ob01700k

  日期：——

  demonstrated. The reaction tolerates various substituted alkynyl carboxylic acids and moderate to good yields of α-pyrone scaffolds have been observed. Later, a gram-scale reaction of the acid and the total synthesis of the natural product pseudopyronine A have been carried out successfully.

  已经证明了 Au( I ) 催化的炔基羧酸的均环化和交叉环化反应，提供了 3,6-二取代的 4-羟基 2 H-吡喃酮。该反应耐受各种取代的炔基羧酸，并观察到中等至良好产率的α-吡喃酮支架。随后，该酸的克级反应和天然产物假吡咯啉A的全合成已成功进行。
• 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
• Inhibition of human sputum elastase by substituted 2-pyrones. 2
  作者：Luisa Cook、Bela Ternai、Peter Ghosh

  DOI：10.1021/jm00389a010

  日期：1987.6

  Nineteen 4-hydroxy- and 4-methoxy-2-pyrones related to elasnin (I) have been assayed for in vitro inhibition of human sputum elastase (HSE), porcine pancreatic elastase, alpha-chymotrypsin, and trypsin. Inhibition is reported as Ki and Ki'; percentage inhibition was dependent on [S] in a number of cases, making it unsuitable as a measure of relative inhibition. The 3-(1-oxoalkyl)-4-hydroxy-6-alkyl-2-pyrones were found to be most effective, the octyl homologue 11 being the most potent inhibitor (Ki = 4.6 microM, 30 times better than the lead compound). A further reduction in inhibition was observed when the hitherto hydrophobic 6-substituent was substituted by a branched functionality of hydrophilic nature. Conversely, methylation of the 4-hydroxy group of the 6-alkyl-2-pyrones increased inhibitory activity. The mechanism of inhibition varied from pure noncompetitive to mixed type to uncompetitive and was found to be dependent on the pattern of substitution. We believe that the 4-hydroxy-2-pyrone binds to the S4 subsite, with the 6-substituent extending across the S4-S1 subsites and the 3-substituent occupying the S5 subsite. The length of the inhibitor binding region was calculated to be approximately 24 A. None of the hydrophobic compounds were found to have any appreciable inhibition (less than 10%) with porcine pancreatic elastase, bovine alpha-chymotrypsin, and bovine trypsin when tested at the limit of their solubility. The hydrophilic compounds were nonspecific, inhibiting all four enzymes. Dialysis was used to show that the interaction is fully reversible.
• EP0365539A4
  申请人：——

  公开号：EP0365539A4

  公开（公告）日：1990-12-05
• HUMAN LEUCOCYTE ELASTASE INHIBITOR COMPOUNDS
  申请人：AUSTRALIAN COMMERCIAL RESEARCH & DEVELOPMENT LIMITED

  公开号：EP0365539A1

  公开（公告）日：1990-05-02