Methanesulfonic acid (Z)-6-(4-methoxy-phenoxy)-hex-3-enyl ester | 151130-70-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methanesulfonic acid (Z)-6-(4-methoxy-phenoxy)-hex-3-enyl ester
• CAS: 151130-70-0
• 化学式: C₁₄H₂₀O₅S
• 分子量: 300.376
• InChiKey: JGWNCRSYYROQKY-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (Z)-6-(4-methoxy-phenoxy)-hex-3-enyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 1-Benzyl-aziridine-2-carboxylic acid benzyl-[(Z)-6-(4-methoxy-phenoxy)-hex-3-enyl]-amide
  参考文献：
  名称：

  Development of a strategy for synthesis of the unusual marine alkaloid sarain A

  摘要：

  An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.

  DOI：

  10.1021/jo00070a035
• 作为产物：
  描述：

  在 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 Methanesulfonic acid (Z)-6-(4-methoxy-phenoxy)-hex-3-enyl ester
  参考文献：
  名称：

  Development of a strategy for synthesis of the unusual marine alkaloid sarain A

  摘要：

  An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.

  DOI：

  10.1021/jo00070a035

文献信息

• Development of a strategy for synthesis of the unusual marine alkaloid sarain A
  作者：Joseph Sisko、James R. Henry、Steven M. Weinreb

  DOI：10.1021/jo00070a035

  日期：1993.8

  An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.