(Z)-1,16-dihydroxy-8-hexadecene | 71042-24-5

• 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: (Z)-1,16-dihydroxy-8-hexadecene
• 英文别名: 1,16-Dihydroxy-cis-8-hexadecen；hexadec-8c-ene-1,16-diol；(Z)-hexadec-8-ene-1,16-diol
• CAS: 71042-24-5
• 化学式: C₁₆H₃₂O₂
• 分子量: 256.429
• InChiKey: VJZGFCYKYJEESC-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1,16-dihydroxy-8-hexadecene 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (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 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 49.0h， 生成 (Z)-1,16-dihydroxy-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

文献信息

• An easy access to symmetrical Z-olefins from phosphorus ylides
  作者：S. Poulain、N. Noiret、H. Patin

  DOI：10.1016/0040-4039(96)01737-6

  日期：1996.10

  Symmetrical Z-olefins are obtained in good to quantitative yields from phosphonium salts via an autoxidation process, in salt-free conditions.

  在无盐条件下，通过自氧化过程，可以从phospho盐以良好的定量收率获得对称的Z-烯烃。
• New synthesis of meromycolic acid
  作者：Walter J. Gensler、R. S. Prasad、Achyuta P. Chaudhuri、Iftekhar Alam

  DOI：10.1021/jo01335a006

  日期：1979.10
• 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