(E)-7-nonadecen-11-one | 63408-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-7-nonadecen-11-one
• 英文别名: (E)-nonadec-12-en-9-one
• CAS: 63408-51-5
• 化学式: C₁₉H₃₆O
• 分子量: 280.494
• InChiKey: LLUGFFSGUQULMF-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-12-(diphenylphosphinyl)-9-(methylthio)-8-dodecene 在 盐酸 、 正丁基锂 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (E)-7-nonadecen-11-one
  参考文献：
  名称：

  Chemistry of cyclic phosphorus compounds. 3. Synthesis of pheromones having an .gamma.,.delta.-unsaturated ketone system from 1,1-diphenylphospholanium perchlorate

  摘要：

  DOI：

  10.1021/jo00265a006

文献信息

• Synthesis and Biological Testing of Ester Pheromone Analogues for Two Fruitworm Moths (Carposinidae)
  作者：Andrew M. Twidle、David M. Suckling、Asha Chhagan、Lisa I. Pilkington、Kye Chung Park、David Barker

  DOI：10.1021/acs.jafc.0c04131

  日期：2020.9.2

  A range of ester pheromone analogues for carposinid moths were synthesized and evaluated for biological activity. The analogues aimed to take advantage of the structural commonality of (7Z)-alken-11-ones found in this family. Analogues were tested on two pest species: Heterocrossa rubophaga and Coscinoptycha improbana. Two of the analogues, (2Z)-nonenyl nonanoate and (4Z)-heptyl undecenoate, elicited

  合成了一系列用于类胡萝卜素的酯信息素类似物，并对其生物学活性进行了评估。这些类似物旨在利用在该家族中发现的（7 Z）-α酮11-酮的结构共性。对两种害虫种类进行了类似物测试：异花杂种和杂种Coscinoptycha improbana。其中的两个类似物，（2 Z）-壬烯基壬酸酯和（4 Z）-庚基十一烯酸酯，引起显着的脑电图反应。仅（4 Z）-十一碳烯酸庚酯在单个sensillum记录中对两种蛾类都给出了一致的响应。分别对这两种类似物以及与两种蛾类中每种信息素的结合进行了野外诱捕试验。蛾类物种对单独的任一类似物均未观察到吸引力。然而，当（4 Z）-十一碳烯酸十一碳酸酯与信息素偶联时，它对红花丝藻产生了强大的抑制作用，使雄蛾的诱捕量降低了95％以上。没有抑制作用的雄性蛾陷阱捕获在C. improbana。
• Organometallic reactions of .omega.-heterosubstituted N-acyl lactams. A new route to .gamma.-keto aldehydes from 5-ethoxy-2-pyrrolidinone
  作者：Diego Savoia、Vittorio Concialini、Sergio Roffia、Luca Tarsi

  DOI：10.1021/jo00005a030

  日期：1991.3

  A new route to gamma-keto aldehydes has been developed in which 5-ethoxy-2-pyrrolidinone is the key intermediate, easily available from 2-pyrrolidinone or succinimide. The lactam undergoes the selective ring opening, previous ''in situ'' N-acylation reaction with pivaloyl chloride or di-tert-butyl dicarbonate and attack of Grignard reagents or pyridyllithium compounds, whereupon the gamma-keto aldehydes are produced by acidic hydrolysis. By this way the gamma-keto aldehydes, which are precursors of natural compounds, such as dihydrojasmone and methyl dihydrojasmonate, a feromone component of the peach fruit moth Carposina niponensis, and nicotine derivatives have been prepared. A practical synthesis of pyridyl-substituted pyrroles (alpha- and beta-nicotyrine and the nor derivatives) can be achieved without purification of the intermediates. N-Acylated 6-ethoxy-2-piperidinone is less reactive toward the organometallic attack, affording in low yields 5-phenyl-5-oxopentanal using phenylmagnesium chloride, and 2-pentylcyclohex-2-en-1-one using n-hexylmagnesium bromide.
• Sorochinskaya, A. M.; Ishchenko, R. I.; Kovalev, B. G., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 237 - 241
  作者：Sorochinskaya, A. M.、Ishchenko, R. I.、Kovalev, B. G.

  DOI：——

  日期：——
• Ramiandrasoa, F.; Descoins, C., Synthetic Communications, 1990, vol. 20, # 13, p. 1989 - 1999
  作者：Ramiandrasoa, F.、Descoins, C.

  DOI：——

  日期：——
• Dasaradhi, Lakkaraju; Rao, Jagadishwar; Bhalerao, Uday T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 167 - 168
  作者：Dasaradhi, Lakkaraju、Rao, Jagadishwar、Bhalerao, Uday T.

  DOI：——

  日期：——