1,16-dithiocyanato-8-hydroxyhexadecane | 382595-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,16-dithiocyanato-8-hydroxyhexadecane
• 英文别名: thiocyanatin A；(8-hydroxy-16-thiocyanatohexadecyl) thiocyanate
• CAS: 382595-10-0
• 化学式: C₁₈H₃₂N₂OS₂
• 分子量: 356.597
• InChiKey: VATLQZFVRAMNQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,16-dithiocyanato-8-hydroxyhexadecane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以65%的产率得到1,16-dithiocarbamyl-8-hydroxyhexadecane
  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：

  (Z)-8-hexadecenedioc acid dimethyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 88.0h， 生成 1,16-dithiocyanato-8-hydroxyhexadecane
  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

• Microwave-Assisted Cross-Metathesis of Unsaturated Thiocyanates: Application to the Synthesis of Thiocyanatins A and B and Analogues
  作者：Olivier Piva、Fanny Cros、Béatrice Pelotier

  DOI：10.1055/s-0029-1217089

  日期：2010.1

  The syntheses of thiocyanatin B and related dithiocyanates have been carried out by cross metathesis of unsaturated thiocyanates promoted by a ruthenium catalyst. The efficiency of the reaction depends strongly on the nature of the catalyst, the length of the alkenyl chain, and the mode of activation (conventional heating or microwave activation). In the later case, isomerization of double bonds took place and altered the course of the reaction. Alternatively, thiocyanatins A and B were synthesized by only a three-step and a two-step procedure, respectively, from readily available tosylates.

  硫氰酸铂 B 和相关二硫代氰酸酯的合成是通过不饱和硫氰酸盐在钌催化剂的促进下进行交叉偏析来实现的。反应的效率在很大程度上取决于催化剂的性质、烯基链的长度和活化方式（传统加热或微波活化）。在后一种情况下，双键发生了异构化，改变了反应的进程。另外，硫氰酸盐 A 和 B 也分别只需三步和两步就能从现成的对甲苯磺酸盐中合成。