4-Hydroxy-6-methyl-5-prop-2-ynylpyran-2-one | 1446991-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-Hydroxy-6-methyl-5-prop-2-ynylpyran-2-one
• 英文别名: 4-hydroxy-6-methyl-5-prop-2-ynylpyran-2-one
• CAS: 1446991-44-1
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: DJTACFPQRMJLOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰丙酮 在 四丁基氟化铵 、 sodium hexamethyldisilazane 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 20.0h， 生成 4-Hydroxy-6-methyl-5-prop-2-ynylpyran-2-one
  参考文献：
  名称：

  Expanding the Structural Diversity of Polyketides by Exploring the Cofactor Tolerance of an Inline Methyltransferase Domain

  摘要：

  A strategy for introducing structural diversity into polyketides by exploiting the promiscuity of an in-line methyltransferase domain in a multidomain polyketide synthase is reported. In vitro investigations using the highly-reducing fungal polyketide synthase CazF revealed that its methyltransferase domain accepts the nonnatural cofactor propargylic Se-adenosyl-L-methionine and can transfer the propargyl moiety onto its growing polyketide chain. This propargylated polyketide product can then be further chain-extended and cyclized to form propargyl-alpha pyrone or be processed fully into the alkyne-containing 4'-propargyl-chaetoviridin A.

  DOI：

  10.1021/ol401723h

文献信息

• Expanding the Structural Diversity of Polyketides by Exploring the Cofactor Tolerance of an Inline Methyltransferase Domain
  作者：Jaclyn M. Winter、Grace Chiou、Ian R. Bothwell、Wei Xu、Neil K. Garg、Minkui Luo、Yi Tang

  DOI：10.1021/ol401723h

  日期：2013.7.19

  A strategy for introducing structural diversity into polyketides by exploiting the promiscuity of an in-line methyltransferase domain in a multidomain polyketide synthase is reported. In vitro investigations using the highly-reducing fungal polyketide synthase CazF revealed that its methyltransferase domain accepts the nonnatural cofactor propargylic Se-adenosyl-L-methionine and can transfer the propargyl moiety onto its growing polyketide chain. This propargylated polyketide product can then be further chain-extended and cyclized to form propargyl-alpha pyrone or be processed fully into the alkyne-containing 4'-propargyl-chaetoviridin A.