13-(tetrahydropyran-2'-yloxy)-1-tridecanol | 176108-76-2

• 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: 13-(tetrahydropyran-2'-yloxy)-1-tridecanol
• 英文别名: 13-(oxan-2-yloxy)tridecan-1-ol
• CAS: 176108-76-2
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: FYKRMVGPVCGGCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  409.4±30.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  21.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  13-(tetrahydropyran-2'-yloxy)-1-tridecanol 在 sodium hexamethyldisilazane 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  花生四烯酸的单一对映异构体的合成

  摘要：

  3-Oxa-2,4-二氧代双环[3.1.0]己烷提供了一种灵活的原料，用于制备单山co酸（一种含有两个远端顺式环丙烷的长链脂肪酸）的对映体。

  DOI：

  10.1016/s0040-4039(00)01147-3
• 作为产物：
  描述：

  1-tetrahydropyranyloxyundecyl-11-triphenylphosphonium bromide 在 palladium on activated charcoal 氢气 作用下， 生成 13-(tetrahydropyran-2'-yloxy)-1-tridecanol
  参考文献：
  名称：

  摘要：

  The cuticular lipids of the wheat stem sawfly Cephus cinctus (Hymenoptera: Cephidae) were investigated as part of a chemical ecology project with this species. The major cuticular lipids were n-alkenes and n-alkanes. Alkenes were the most abundant and exhibited dramatic sexual dimorphism. (Z)-9-Tricosene accounted for about half of the total hydrocarbon in males but was nearly absent from females. The dominant alkenes in females were (Z)-9-pentacosene and (Z)-9-heptacosene. The alkane profiles were similar in both sexes, with n-tricosane being the most abundant, followed by n-pentacosane and n-heptacosane. In both sexes, there were minor amounts of alkanes and alkenes with other chain lengths and n-alkadienes of 29 and 31 carbons. In males, about one tenth of the surface lipids consisted of (Z)-9-alkene-1, omega-diol diacetates with 22-, 24-, and 26-carbon chains. The same compounds were also detected from females but in much smaller amounts. The structures of these novel diacetates were proven by synthesis. By analogy to methyl oleate, a well-studied food lipid, the alkenes and diacetates were expected to undergo slow oxidation in air to release specific aldehydes and other volatile products, and these were generally detected in volatiles collected from living sawflies. Atmospheric oxidation of the diacetates was also demonstrated in the absence of sawflies. One product from the diacetates, 9-acetyloxynonanal, was shown in other research to be particularly active electrophysiologically and was also attractive in the field. Aldehydes from the alkenes also showed strong electrophysiological activity. The concept of volatile pheromones originating from heavy, unsaturated cuticular lipids is discussed.

  DOI：

  10.1023/a:1017994410538

文献信息

• Synthesis of Squamostanal-A
  作者：Hiroyuki Konno、Hidefumi Makabe、Akira Tanaka、Takayuki Oritani

  DOI：10.1271/bbb.60.526

  日期：1996.1

  The first synthesis of squamostanal-A (1), separated as a degradation product of tetrahydrofuranic acetogenins, is described. Iodide 7, which corresponds to the latent aldehyde moiety of 1, was prepared through a 2-step sequence from 13-[tetrahydropyran-2'- yloxy]-2-tridecyn-l-ol (5). The NaHMDS-based coupling reaction of 7 with γ-lactone 8 gave compound 9, which by a 3-step sequence, was coverted to 1

  本文描述了作为四氢呋喃苷元降解产物分离出来的角鲨烷-A（1）的首次合成。碘化物 7 与 1 的潜在醛基相对应，它是由 13-[四氢吡喃-2'-氧基]-2-十三炔-l-醇（5）通过两步法制备的。7 与γ-内酯 8 发生基于 NaHMDS 的偶联反应，得到化合物 9，并通过 3 步顺序将其转化为 1
• <i>Z</i>-Selective Intramolecular Horner−Wadsworth−Emmons Reaction for the Synthesis of Macrocyclic Lactones
  作者：Kaori Ando、Kenji Narumiya、Hirokazu Takada、Taiji Teruya

  DOI：10.1021/ol100071d

  日期：2010.4.2

  When the substrates (ArO)(2)P(O)CH2CO2-CHO (Ar = Ph, o-t-BuPh) were added to a THF solution containing 3 equiv of NaH at 0 degrees C or NaI-DBU at rt over 1-10 h, the Intramolecular Horner-Wadsworth-Emmons reaction proceeded efficiently to give the 12-18-membered-ring lactones in 69-93% yields with 89-100% Z selectivity. On the other hand, (EtO)(2)P(O)CH2CO2-CHO gave the 13-18-membered-ring lactones in 52-82% yields with 89-99% E selectivity using LiCl-DBU in MeCN or THF.