(R)-4-methyldodecanal | 927868-89-1

• 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: (R)-4-methyldodecanal
• 英文别名: (4R)-4-methyldodecanal
• CAS: 927868-89-1
• 化学式: C₁₃H₂₆O
• 分子量: 198.349
• InChiKey: MKZKRCROQPZLMF-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-4-methyldodecanal 在 吡啶 、 4-二甲氨基吡啶 、 aluminum oxide 、 potassium permanganate 、 四丁基溴化铵 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 181.0h， 生成 3-O-benzyl-2-O-((R)-10-methyloctadecanoyl)-1-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and Structure of Phosphatidylinositol Dimannoside

  摘要：

  (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (S)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl)phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.

  DOI：

  10.1021/jo0625599
• 作为产物：
  描述：

  己基溴化镁 在 lithium aluminium tetrahydride 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 (R)-4-methyldodecanal
  参考文献：
  名称：

  由甲基化的四烯酸脂肪酸形成的手性聚集体：由单个对映异构体和时间依赖性立体突变形成的两个手性聚集体的对映体。

  摘要：

  甲基化的丁烯二酸（TE-FAs）的手性聚集体的形成和行为已有报道。在C-24 TE-FA系列中，通过将C-24 TE-FA 1b的乙醇储备溶液分散到磷酸钠缓冲液中制备的聚集体产生很强的棉花效应，而由甲醇储备溶液制备的聚集体产生负的棉花效应。棉花效果。在C-20 TE-FA系列中，由C-20 TE-FA 2b的乙醇储备溶液制得的聚集体表现出随时间变化的手性反转。[见文字]。

  DOI：

  10.1021/ol062834d

文献信息

• Contact sex pheromone component of the Emerald Ash Borer Agrilus planipennis Fairmaire (Coleoptera: Buprestidae)
  申请人：Silk Peter

  公开号：US20100143429A1

  公开（公告）日：2010-06-10

  The invention disclosed relates to the detection of the Emerald Ash Borer (EAB), Agrilus planipennis Fairmaire (Coleoptra: B-prestidae) and in particular to the use of contact sex phenomones therefor. Analyses of the elytral hydrocarbons from male and female emerald ash borer, that were freshly emerged vs. sexually mature (>10 days old) revealed a female-specific compound, 9-methyl-pentacosane (9-Me-C 25 ), only present in sexually mature females. This material was synthesized by the Wittig reaction of 2-decanone with (n-hexadecyl)-triphenylphosphonium bromide followed by catalytic reduction to yield racemic 9-Me C 25 , which matched the natural compound by GC/MS (retention time and EI-mass spectrum). In field bioassays with freeze-killed sexually mature A. planipennis females, feral males spent significantly more time in contact and attempting copulation with unwashed females than with females that had been washed in n-hexane to remove the cuticular hydrocarbons. Hexane-washed females to which 9-Me-C 25 had been reapplied elicited similar contact time and percentage of time attempting copulation as unwashed females, indicating that 9-methyl-pentacosane is a contact sex-pheromone component of A. planipennis . This is the first contact sex pheromone identified in the Buprestidae.

  该发明涉及检测翠绿山梨树天牛（EAB），即平板天牛（Agrilus planipennis Fairmaire）（鞘翅目：B-prestidae），特别是其接触性性信息素的使用。对新出现和性成熟（>10天）的雄性和雌性翠绿山梨树天牛的鞘翅烃的分析显示，只有性成熟雌性才含有一种特异的化合物，即9-甲基-戊二十五烷（9-Me-C25）。通过2-癸酮与（正十六烷基）三苯基膦溴化铵的Wittig反应合成了这种物质，然后经催化还原得到外消旋的9-Me C25，通过GC/MS（保留时间和EI-质谱）与天然化合物相匹配。在使用冷冻杀死的性成熟A. planipennis雌性进行的野外生物测定中，野外雄性与未清洗的雌性接触并尝试交配的时间明显多于与用正己烷清洗去除角质烃的雌性。重新涂抹了9-Me-C25的正己烷清洗的雌性引起了与未清洗雌性相似的接触时间和尝试交配的时间百分比，表明9-甲基-戊二十五烷是A. planipennis的接触性性信息素成分。这是首次在平板天牛科中鉴定的接触性性信息素。
• A new short synthesis of 10R-tuberculostearic acid and its enantiomer
  作者：Ieuan O. Roberts、Mark S. Baird

  DOI：10.1016/j.chemphyslip.2006.03.006

  日期：2006.7

  Tuberculostearic acid (10R-methyloctadecanoic acid) and its 10S-enantiomer were synthesised by a chiral pool strategy, in four steps from citronellyl bromide. (c) 2006 Elsevier Ireland Ltd. All rights reserved.
• US8404225B2
  申请人：——

  公开号：US8404225B2

  公开（公告）日：2013-03-26