(6E,8Z,10S)-10-(methoxymethoxy)pentadeca-6,8-diene | 1225291-86-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6E,8Z,10S)-10-(methoxymethoxy)pentadeca-6,8-diene
• CAS: 1225291-86-0
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: AGFIJUCGNBNBJI-ZGDBIHKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6E,8Z,10S)-10-(methoxymethoxy)pentadeca-6,8-diene 在 水 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以83%的产率得到(Z,6R,7R,10S)-10-(methoxymethoxy)pentadec-8-ene-6,7-diol
  参考文献：
  名称：

  Synthesis of the 1,2-Anti Type of 3E-Alkene-1,2,5-triol Derivatives

  摘要：

  We invented an efficient method to obtain 3E-alkene-1,2,5-triol derivatives with 1,2-anti stereochemistry from the 2Z,4E-alkadienyl alcohol derivatives, which were synthesized by using nickel-catalyzed coupling between lithium 1E-alkenyl borates and 1-halo-1Z-alken-3-ols. The method involves (1) asymmetric dihydroxylation at the E olefin moiety of the dienyl alcohol derivatives followed by formation of a cyclic carbonates; (2) palladium-catalyzed reaction with AcOH in the presence of Et(3)N. The method was applied successfully to the synthesis of the C6-C20 part of trioxilin A(3).

  DOI：

  10.3987/com-09-s(s)89
• 作为产物：
  描述：

  (Z)-(S)-1-Bromo-oct-1-en-3-ol 、 氯甲基甲基醚 、 (E)-2-(1-heptenyl)-5,5-dimethyl-1,3,2-dioxaborinane 在 甲基锂 、 N,N-二异丙基乙胺 作用下， 生成 (6E,8Z,10S)-10-(methoxymethoxy)pentadeca-6,8-diene
  参考文献：
  名称：

  Synthesis of the 1,2-Anti Type of 3E-Alkene-1,2,5-triol Derivatives

  摘要：

  We invented an efficient method to obtain 3E-alkene-1,2,5-triol derivatives with 1,2-anti stereochemistry from the 2Z,4E-alkadienyl alcohol derivatives, which were synthesized by using nickel-catalyzed coupling between lithium 1E-alkenyl borates and 1-halo-1Z-alken-3-ols. The method involves (1) asymmetric dihydroxylation at the E olefin moiety of the dienyl alcohol derivatives followed by formation of a cyclic carbonates; (2) palladium-catalyzed reaction with AcOH in the presence of Et(3)N. The method was applied successfully to the synthesis of the C6-C20 part of trioxilin A(3).

  DOI：

  10.3987/com-09-s(s)89

文献信息

• Synthesis of the 1,2-Anti Type of 3E-Alkene-1,2,5-triol Derivatives
  作者：Yuichi Kobayashi、Akira Takeuchi、Hatsuhiko Hattori

  DOI：10.3987/com-09-s(s)89

  日期：——

  We invented an efficient method to obtain 3E-alkene-1,2,5-triol derivatives with 1,2-anti stereochemistry from the 2Z,4E-alkadienyl alcohol derivatives, which were synthesized by using nickel-catalyzed coupling between lithium 1E-alkenyl borates and 1-halo-1Z-alken-3-ols. The method involves (1) asymmetric dihydroxylation at the E olefin moiety of the dienyl alcohol derivatives followed by formation of a cyclic carbonates; (2) palladium-catalyzed reaction with AcOH in the presence of Et(3)N. The method was applied successfully to the synthesis of the C6-C20 part of trioxilin A(3).