(Z)-(R)-15-(tert-Butyl-dimethyl-silanyloxy)-hexadec-12-enoic acid | 212012-93-6

• 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: (Z)-(R)-15-(tert-Butyl-dimethyl-silanyloxy)-hexadec-12-enoic acid
• CAS: 212012-93-6
• 化学式: C₂₂H₄₄O₃Si
• 分子量: 384.675
• InChiKey: VZKXUOYYWWRMPY-FZWACIFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  26.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-15-(tert-Butyl-dimethyl-silanyloxy)-hexadec-12-enoic acid 在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 (R,Z)-15-hydroxy-12-hexadecenoic acid
  参考文献：
  名称：

  Synthesis of Both Enantiomers of 15-Hexadecanolide, a Sex Pheromone Component of the Stink Bug,Piezodorus hybneri

  摘要：

  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。

  DOI：

  10.1271/bbb.62.1261
• 作为产物：
  描述：

  12-溴十二烷酸 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 甲苯 、 乙腈 为溶剂， 反应 128.83h， 生成 (Z)-(R)-15-(tert-Butyl-dimethyl-silanyloxy)-hexadec-12-enoic acid
  参考文献：
  名称：

  Synthesis of Both Enantiomers of 15-Hexadecanolide, a Sex Pheromone Component of the Stink Bug,Piezodorus hybneri

  摘要：

  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。

  DOI：

  10.1271/bbb.62.1261

文献信息

• ——
  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.