[(Z)-16-methylsulfonyloxyhexadec-8-enyl] methanesulfonate | 380896-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [(Z)-16-methylsulfonyloxyhexadec-8-enyl] methanesulfonate
• CAS: 380896-56-0
• 化学式: C₁₈H₃₆O₆S₂
• 分子量: 412.612
• InChiKey: IGYHHQCKLKNOQB-ARJAWSKDSA-N

物化性质

• 沸点：
  573.7±43.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium thioacyanate 、 [(Z)-16-methylsulfonyloxyhexadec-8-enyl] methanesulfonate 以 乙醇 为溶剂， 反应 16.0h， 以60%的产率得到(Z)-1,16-dithiocyanato-8-hexadecene
  参考文献：
  名称：

  The Isolation and Synthesis of Novel Nematocidal Dithiocyanates from an Australian Marine Sponge, Oceanapia sp.

  摘要：

  Bioassay-directed fractionation of the EtOH extract of an Oceanapia sp. collected off the northern Rottnest Shelf, Australia, has yielded three novel dithiocyanates, thiocyanatins A (1), B (2a), and C (2b). The structures were determined by detailed spectroscopic analysis and confirmed by total synthesis. In addition to featuring an unprecedented dithiocyanate functionality, thiocyanatins possess an unusual 1,16-difunctionalized n-hexadecane carbon skeleton and are revealed as a hitherto unknown class of nematocidal agents

  DOI：

  10.1021/jo0106750
• 作为产物：
  描述：

  8-溴辛酸 在 N,N-二甲基丙烯基脲 、 lithium aluminium tetrahydride 、 硫酸 、 氧气 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 50.0h， 生成 [(Z)-16-methylsulfonyloxyhexadec-8-enyl] methanesulfonate
  参考文献：
  名称：

  The Isolation and Synthesis of Novel Nematocidal Dithiocyanates from an Australian Marine Sponge, Oceanapia sp.

  摘要：

  Bioassay-directed fractionation of the EtOH extract of an Oceanapia sp. collected off the northern Rottnest Shelf, Australia, has yielded three novel dithiocyanates, thiocyanatins A (1), B (2a), and C (2b). The structures were determined by detailed spectroscopic analysis and confirmed by total synthesis. In addition to featuring an unprecedented dithiocyanate functionality, thiocyanatins possess an unusual 1,16-difunctionalized n-hexadecane carbon skeleton and are revealed as a hitherto unknown class of nematocidal agents

  DOI：

  10.1021/jo0106750

文献信息

• The Isolation and Synthesis of Novel Nematocidal Dithiocyanates from an Australian Marine Sponge, <i>Oceanapia </i>sp.
  作者：Robert J. Capon、Colin Skene、Edward Hsiang-Te Liu、Ernest Lacey、Jennifer H. Gill、Kirstin Heiland、Thomas Friedel

  DOI：10.1021/jo0106750

  日期：2001.11.1

  Bioassay-directed fractionation of the EtOH extract of an Oceanapia sp. collected off the northern Rottnest Shelf, Australia, has yielded three novel dithiocyanates, thiocyanatins A (1), B (2a), and C (2b). The structures were determined by detailed spectroscopic analysis and confirmed by total synthesis. In addition to featuring an unprecedented dithiocyanate functionality, thiocyanatins possess an unusual 1,16-difunctionalized n-hexadecane carbon skeleton and are revealed as a hitherto unknown class of nematocidal agents