1,9,18-trihydroxyoctadecane | 719287-13-5

• 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: 1,9,18-trihydroxyoctadecane
• 英文别名: Octadecane-1,9,18-triol
• CAS: 719287-13-5
• 化学式: C₁₈H₃₈O₃
• 分子量: 302.498
• InChiKey: VHNYRSLRUMRKOG-UHFFFAOYSA-N

物化性质

• 熔点：
  58-62 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  440.0±10.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  17
• 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：

  1,9,18-trihydroxyoctadecane 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 32.0h， 以42%的产率得到[10-Hydroxy-18-(4-methylphenyl)sulfonyloxyoctadecyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Nematocidal Thiocyanatins from a Southern Australian Marine Sponge Oceanapia sp.

  摘要：

  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.

  DOI：

  10.1021/np049977y
• 作为产物：
  描述：

  2-(9-溴壬基-1-氧基)四氢吡喃 在 N,N-二甲基丙烯基脲 、 lithium aluminium tetrahydride 、 硫酸 、 sodium hexamethyldisilazane 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 82.5h， 生成 1,9,18-trihydroxyoctadecane
  参考文献：
  名称：

  Nematocidal Thiocyanatins from a Southern Australian Marine Sponge Oceanapia sp.

  摘要：

  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.

  DOI：

  10.1021/np049977y