6-((2S,4R)-2,4,11-trihydroxyundecyl)-4-hydroxy-3-methyl-2H-pyran-2-one | 1542981-22-5

• 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: 6-((2S,4R)-2,4,11-trihydroxyundecyl)-4-hydroxy-3-methyl-2H-pyran-2-one
• 英文别名: 4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxyundecyl)-2H-pyran-2-one；4-hydroxy-3-methyl-6-[(2S,4R)-2,4,11-trihydroxyundecyl]pyran-2-one
• CAS: 1542981-22-5
• 化学式: C₁₇H₂₈O₆
• 分子量: 328.406
• InChiKey: NAFBSCAXPHZFLQ-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,8-辛二醇 在 2,6-二甲基吡啶 、 camphor-10-sulfonic acid 、 sodium acetate 、 四氯化钛 、 sodium hydride 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 mineral oil 、 苯 为溶剂， 反应 8.86h， 生成 6-((2S,4R)-2,4,11-trihydroxyundecyl)-4-hydroxy-3-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis and Determination of Absolute Configuration of α-Pyrones Isolated from Penicillium corylophilum

  摘要：

  The first total synthesis of (S)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one, 4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxyundecyl)-2H-pyran-2-one, and its unnatural 2R,4R-isomer starting from commercially available 1,8-octanediol is described. The synthesis led to the revision of the proposed structural assignment of the natural product as (R)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one. The key steps include chiral auxiliary mediated asymmetric acetate aldol reaction, dianion addition, and base mediated cyclization to form an alpha-pyrone ring.

  DOI：

  10.1021/jo5015382

文献信息

• Synthesis and Determination of Absolute Configuration of α-Pyrones Isolated from <i>Penicillium corylophilum</i>
  作者：J. S. Yadav、B. Ganganna、Palash Dutta、Kiran K Singarapu

  DOI：10.1021/jo5015382

  日期：2014.11.21

  The first total synthesis of (S)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one, 4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxyundecyl)-2H-pyran-2-one, and its unnatural 2R,4R-isomer starting from commercially available 1,8-octanediol is described. The synthesis led to the revision of the proposed structural assignment of the natural product as (R)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one. The key steps include chiral auxiliary mediated asymmetric acetate aldol reaction, dianion addition, and base mediated cyclization to form an alpha-pyrone ring.