13-tetrahydropyranyloxytridecanal | 304435-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 13-tetrahydropyranyloxytridecanal
• 英文别名: 13-((tetrahydro-2H-pyran-2-yl)oxy)tridecanal；13-(oxan-2-yloxy)tridecanal
• CAS: 304435-28-7
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: AFHKVRKVCQVZCP-UHFFFAOYSA-N

物化性质

• 沸点：
  404.3±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)：
  5.02
• 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：
  0.94
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  13-tetrahydropyranyloxytridecanal 在 potassium permanganate 、 sodium periodate 、 硫酸 、 十六烷基三甲基溴化铵 、 sodium hexamethyldisilazane 、 potassium carbonate 、 对甲苯磺酸 、 copper(II) sulfate 、 间氯过氧苯甲酸 、 三苯基膦 、 肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 异丙醇 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：

  2-[(11-bromoundecyl)oxy]tetrahydro-2H-pyran 在 palladium on activated charcoal 重铬酸吡啶 、 氢气 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 13-tetrahydropyranyloxytridecanal
  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

• Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**
  作者：Guillaume Force、Anna Perfetto、Robert J. Mayer、Ilaria Ciofini、David Lebœuf

  DOI：10.1002/anie.202105882

  日期：2021.9

  towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables

  大环内酯是一类特殊的天然和合成产品，在精细化学品和制药行业有着广泛的应用。尽管在合成方面取得了所有进展，特别是从seco-酸，一种有效的、选择性的、灵活的、容易获得的并且尽可能与多种官能团相容的大环内酯化促进剂系统仍然缺乏。在这里，我们描述了一种策略，该策略依赖于形成包含五氟苯基的混合酸酐，由于其高电子活化，可以方便地获得具有广泛多功能性的大环内酯、大二内酯和酯。进行动力学研究和 DFT 计算以合理化五氟苯基在大环内酯化反应中的反应性。