(R)-(-)-15-hexadecanolide | 69297-56-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (R)-(-)-15-hexadecanolide
• 英文别名: 15R-Hexadecanolide；(16R)-16-methyl-oxacyclohexadecan-2-one
• CAS: 69297-56-9
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: GILZFLFJYUGJLX-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,10-癸二醇 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 LiOH-H₃PO₄-AcOH-H₃BO₃ buffer 、 盐酸羟胺 、 氢溴酸 、 氢气 、 sodium hexamethyldisilazane 、 magnesium sulfate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 214.33h， 生成 (R)-(-)-15-hexadecanolide
  参考文献：
  名称：

  Synthese der natürlichenR-( - )Enantiomere dreier Galbanum-Harz Macrolide

  摘要：

  从格巴胶树脂中分离出的三种大环内酯1、2和3，是以α-溴缩醛9为起始物进行合成的。关键步骤是亚甲基腾内镉14和23的缓冲内分子Wittig反应，生成α,β-不饱和内酯15、16和24。这些内酯的氢化反应得到了(R)-构型的目标大环内酯。

  DOI：

  10.1055/s-1994-25676

文献信息

• Synthesis of Both Enantiomers of 15-Hexadecanolide, a Sex Pheromone Component of the Stink Bug,<i>Piezodorus hybneri</i>
  作者：Shigefumi KUWAHARA、Tomoko TSURUTA、Walter Soares LEAL、Osamu KODAMA

  DOI：10.1271/bbb.62.1261

  日期：1998.1

  Both enantiomers of 15-hexadecanolide, a sex pheromone component of the stink bug (Piezodorus hybneri), were synthesized by using the Yamaguchi or Mitsunobu macrolactonization reaction of (R)-15-hydroxyhexadecanoic acid prepared from ethyl (R)-β-hydroxybutyrate in 5 steps.

  通过对 (R)-β-hydroxybutyrate 乙酯制备的 (R)-15-hydroxyhexadecanoic acid（(R)-15-羟基十六烷酸）进行山口或 Mitsunobu 大内酯化反应，分 5 个步骤合成了臭虫（Piezodorus hybneri）性信息素成分 15-十六烷内酯的两种对映体。
• Synthesis of Both Enantiomers of Four Different Macrocyclic Lactones
  作者：Yoshihiro Noda、Hitoshi Kashin

  DOI：10.3987/com-97-7991

  日期：——

  Both enantiomers of macrocyclic lactones, 12-tridecanolide (1), 13-tetradecanolide (2), 14-pentadecanolide (3) and 15-hexadecanolide (4), were synthesized utilizing (S)-(-)-beta-hydroxythioacetal (5) as the chiral building block. Key steps are the C-alkylation of a dianion derived from 5 with alkyl dibromides followed by conversion of functional groups and the two macrolactonization. The both enantiomers of 1 similar to 4 have been obtained by reductive desulfurization of the dithiane moiety.
• Chemoenzymatic preparation of musky macrolactones
  作者：Tancredi Fortunati、Mariantonietta D'Acunto、Tonino Caruso、Aldo Spinella

  DOI：10.1016/j.tet.2015.03.007

  日期：2015.4

  A chemoenzymatic approach to some musk macrolactones has been explored by the optimization of macrolactonization catalyzed by Candida antarctica lipase B (Novozym 435). This fast and high yield optimized methodology represents a large improvement to previously reported results. The methodology was applied to the preparation of 16-hexadecanolide, exaltolide, ambrettolide and (15R)-15-hexadecanolide. (C) 2015 Elsevier Ltd. All rights reserved.
• ——
  作者：Walter Soares Leal、Shigefumi Kuwahara、Xiongwei Shi、Hiroya Higuchi、Claudia E. B. Marino、Mikio Ono、Jerrold Meinwald

  DOI：10.1023/a:1022307600446

  日期：——

  Male-released semiochemicals of the stink bug Piezodorus hybneri (Heteroptera: Pentatomidae) elicit attraction of male and female bugs and homosexual behavior in males. Three active components were isolated from the airborne volatiles of males by flash chromatography, with the activity monitored by GC-EAD and behavioral bioassay. The pheromone system was characterized as a mixture of beta-sesquiphellandrene, (R)-15-hexadecanolide, and methyl 8-(Z)-hexadecenoate (ratio: 10:4:1), and the activity of the semiochemicals was assessed with authentic samples. Enantiomerically pure samples of the R and S macrolactones were obtained by Yamaguchi's and Mitsunobu's macrolactonization of a key intermediate, (R)-15-hydroxyhexadecanoic acid. The nonnatural S stereoisomer was neither a beneficial nor a behavioral antagonist. Individual constituents or binary mixtures were active, but the optimal male response was elicited only by the full mixture. Behavioral observation and the fact that the onset of pheromone production is coincident with ovarian development strongly suggest that these semiochemicals are, in fact, sex pheromones.
• STANCHEV, STEPHAN;HESSE, MANFRED, HELV. CHIM. ACTA., 72,(1989) N, C. 1052-1060
  作者：STANCHEV, STEPHAN、HESSE, MANFRED

  DOI：——

  日期：——