methyl 4-acetyl-3-oxo-7-(trimethylsilyl)hept-6-ynoate | 1446991-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 4-acetyl-3-oxo-7-(trimethylsilyl)hept-6-ynoate
• CAS: 1446991-45-2
• 化学式: C₁₃H₂₀O₄Si
• 分子量: 268.385
• InChiKey: HCYCTHCBLQENRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-acetyl-3-oxo-7-(trimethylsilyl)hept-6-ynoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 3.0h， 以76%的产率得到4-hydroxy-6-methyl-5-(3-(trimethylsilyl)prop-2-yn-1-yl)-2H-pyran-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
• 作为产物：
  描述：

  乙酰丙酮 在 sodium hexamethyldisilazane 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 生成 methyl 4-acetyl-3-oxo-7-(trimethylsilyl)hept-6-ynoate
  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