(2S,3Z)-2-ethyl-5-(4-methoxybenzyloxy)-3-hexen-1-ol | 1040233-49-5

• 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: (2S,3Z)-2-ethyl-5-(4-methoxybenzyloxy)-3-hexen-1-ol
• CAS: 1040233-49-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: DLIXYDDOCUCHRP-ZFDPJTLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3Z)-2-ethyl-5-(4-methoxybenzyloxy)-3-hexen-1-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到(2S,3Z)-2-ethyl-5-(4-methoxybenzyloxy)-3-pentenal
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  Leustroducsin B was synthesized via a convergent route based on division of the leustroducsin molecule into three segments A, B, and C. Two coupling reactions (Julia coupling reaction and Nozaki-Hiyama-Kishi (NHK) reaction) were employed for coupling of segments A and 13: segment A, for the Julia coupling reaction was prepared by a combination of Sharpless asymmetric epoxidation and an epoxide-cleavage reaction with an organoaluminum reagent, while segment A, for the NHK reaction was synthesized from optically active alcohol that had previously been prepared by lipase-catalyzed kinetic resolution. Segment B, whose structure was modified with some functional groups, was synthesized from (R)-malic acid by a combination of Wittig reaction and Sharpless asymmetric dihydroxylation, and segment C, containing a cyclohexane moiety, was prepared by asymmetric Diels-Alder reaction. Segment B was first coupled with segment A, via the Julia coupling reaction, but the yield was low due to unexpected epimerization. The NHK reaction of segment A2 proceeded to give the coupling product in good yield. This product was coupled with segment C via Wittig and Stille coupling reactions, and finally, phosphorylation was carried out by partial hydrolysis of a cyclic phosphate to give leustroducsin B.

  DOI：

  10.1021/jo8005599
• 作为产物：
  描述：

  在 DOWEX 50W-X₂ 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以588 mg的产率得到(2S,3Z)-2-ethyl-5-(4-methoxybenzyloxy)-3-hexen-1-ol
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  Leustroducsin B was synthesized via a convergent route based on division of the leustroducsin molecule into three segments A, B, and C. Two coupling reactions (Julia coupling reaction and Nozaki-Hiyama-Kishi (NHK) reaction) were employed for coupling of segments A and 13: segment A, for the Julia coupling reaction was prepared by a combination of Sharpless asymmetric epoxidation and an epoxide-cleavage reaction with an organoaluminum reagent, while segment A, for the NHK reaction was synthesized from optically active alcohol that had previously been prepared by lipase-catalyzed kinetic resolution. Segment B, whose structure was modified with some functional groups, was synthesized from (R)-malic acid by a combination of Wittig reaction and Sharpless asymmetric dihydroxylation, and segment C, containing a cyclohexane moiety, was prepared by asymmetric Diels-Alder reaction. Segment B was first coupled with segment A, via the Julia coupling reaction, but the yield was low due to unexpected epimerization. The NHK reaction of segment A2 proceeded to give the coupling product in good yield. This product was coupled with segment C via Wittig and Stille coupling reactions, and finally, phosphorylation was carried out by partial hydrolysis of a cyclic phosphate to give leustroducsin B.

  DOI：

  10.1021/jo8005599