(S,2Z,4E)-2-iodo-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-diene-1,7-diol | 935872-68-7

• 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: (S,2Z,4E)-2-iodo-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-diene-1,7-diol
• 英文别名: (2Z,4E,7S)-2-iodo-7-[(1R,2R)-2-[(4-methoxyphenyl)methoxymethyl]cyclopentyl]hepta-2,4-diene-1,7-diol
• CAS: 935872-68-7
• 化学式: C₂₁H₂₉IO₄
• 分子量: 472.363
• InChiKey: JVJZOHHYBYQYSX-LUCRLEBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,2Z,4E)-2-iodo-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-diene-1,7-diol 、 三异丙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到(S,3E,5Z)-6-iodo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-(triisopropylsilyloxy)hepta-3,5-dien-1-ol
  参考文献：
  名称：

  Total Synthesis of Borrelidin

  摘要：

  The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2 center dot Et2O-mediated chelation-controlled allylation.

  DOI：

  10.1021/jo062089i
• 作为产物：
  描述：

  在 吡啶 、 sodium periodate 、 四丁基溴化铵 、 水 、 二异丁基氢化铝 、 potassium carbonate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 79.0h， 生成 (S,2Z,4E)-2-iodo-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-diene-1,7-diol
  参考文献：
  名称：

  Total Synthesis of Borrelidin

  摘要：

  The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2 center dot Et2O-mediated chelation-controlled allylation.

  DOI：

  10.1021/jo062089i