1,8,16-trihydroxyhexadecane | 58115-24-5

• 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: 1,8,16-trihydroxyhexadecane
• 英文别名: hexadecane-1,8,16-triol
• CAS: 58115-24-5
• 化学式: C₁₆H₃₄O₃
• 分子量: 274.444
• InChiKey: ZXSWHIBNTACELR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,8,16-trihydroxyhexadecane 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 (E)-16-{[(4-methylphenyl)sulfonyl]oxy}hexadec-8-enyl 4-methylbenzenesulfonate
  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 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 84.0h， 生成 1,8,16-trihydroxyhexadecane
  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

• New synthesis of nematocidal natural products dithiocynates thiocyanatin A and 1,8,16-trihydroxyhexadecane
  作者：Ashima Singh、M.L. Sharma、Jasvinder Singh

  DOI：10.1080/14786410802587073

  日期：2009.7.20

  A new and short synthesis of nematocidal natural products, thiocyanatin A and 1,8,16-trihydroxyhexadecane, from readily available starting compounds 1,7-heptanediol and 1,9-nonanediol in six steps is described.
• Nematocidal Thiocyanatins from a Southern 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/np049977y

  日期：2004.8.1

  Investigations of a southern Australian marine sponge, Oceanapia sp., have yielded two new methyl branched bisthiocyanates, thiocyanatins D-1 (3a) and D-2 (3b), along with two new thiocarbamate thiocyanates, thiocyanatins E-l (4a) and E-2 (4b). The new thiocyanatins belong to a rare class of bioactive marine metabolite previously only represented by thiocyanatins A-C (1, 2a/b). Structures were assigned on the basis of detailed spectroscopic analysis, with comparisons to the known bisthiocyanate thiocyanatin A (1) and synthetic model compounds (5-7). The thiocyanatins exhibit potent nematocidal activity, and preliminary structure-activity relationship investigations have confirmed key characteristics of the thiocyanatin pharmacophore.