methyl (2S)-2-(oxan-2-yloxymethyl)-2-pent-4-enoyloxypent-4-enoate | 1134400-97-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2S)-2-(oxan-2-yloxymethyl)-2-pent-4-enoyloxypent-4-enoate
• CAS: 1134400-97-7
• 化学式: C₁₇H₂₆O₆
• 分子量: 326.39
• InChiKey: RLNVHIVNCNREKW-LWKPJOBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-(oxan-2-yloxymethyl)-2-pent-4-enoyloxypent-4-enoate 在 lithium hexamethyldisilazane 、 氯甲基甲基醚 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以88%的产率得到4-(methoxymethoxy)-5-(oxan-2-yloxymethyl)-3,5-bis(prop-2-enyl)furan-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative

  摘要：

  A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched alpha-acyloxy-alpha,alpha-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.

  DOI：

  10.3987/com-08-s(f)11
• 作为产物：
  描述：

  4-戊烯酰氯 、 methyl (2S)-2-hydroxy-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pent-4-enoate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到methyl (2S)-2-(oxan-2-yloxymethyl)-2-pent-4-enoyloxypent-4-enoate
  参考文献：
  名称：

  Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative

  摘要：

  A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched alpha-acyloxy-alpha,alpha-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.

  DOI：

  10.3987/com-08-s(f)11

文献信息

• Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative
  作者：Ken-ichi Takao、Kin-ichi Tadano、Yuki Kojima、Tomo Miyashita、Kentaro Yashiro、Tatsuya Yamada

  DOI：10.3987/com-08-s(f)11

  日期：——

  A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched alpha-acyloxy-alpha,alpha-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.